Molecules with Silly or Unusual Names

Believe it or not, some chemists do have a sense of humour, and this page is a testament to that. Here we'll show you some real molecules that have unusual, ridiculous or downright silly names. If you know of any other potential candidates for this page, please let me know. People from all over the world have sent me so many contributions to this page, that I've now had to split it into three smaller pages.

The 3D structure files of many of these molecules can be obtained by clicking on the images. Information on what you need to view these structure files can be found here.

Stop Press: Due to the popularity of this site, I've now written it up as a book, entitled 'Molecules with Silly or Unusual

Names', by Paul May, to be published by World Scientific Press, Summer/Autumn 2008. It should be available at all good bookstores. It will include all your favourite molecules from this website, plus some extra information about them. More details shortly...

Arsole

Yes, believe it or not, there is actually a molecule called Arsole... and it's a ring! It is the arsenic equivalent of pyrrole, and although it is rarely found in its pure form, it is occasionally seen as a sidegroup in the form of organic arsolyls. For more information, see the paper with probably the best title of any scientific paper I've ever come across: "Studies on the Chemistry of the Arsoles", G. Markl and H. Hauptmann, J. Organomet. Chem., 248 (1983) 269. Contrary to popular belief, new research (see reference below) shows that arsoles are only moderately aromatic... Incidentally US patent number US 3 412 119 by the Dow Chemical Company is entitled 'Substituted Stannoles, Phospholes, Arsoles, and Stiboles' - I didn't know there was a substitute for an arsole...Furthermore, the structure where arsole is fused to a benzene ring is called 'benzarsole', and apparently when it's fused to 6 benzenes it would be called 'sexibenzarsole' (although that molecule hasn't been synthesised yet). Another well known poisonous arsenic molecule is the simple hydride, called 'arsine', with formula AsH3.And on a related theme, I've been told of an Aryl Selenide compound with the superb shorthand of ArSe, which is both toxic and smelly. The paper it comes from in J. Am. Chem. Soc. was published by authors from, of course, the University of Aarhus!Also, the related molecule phosphole (which just replaces As with P) is quite amusing if you are a French speaker, since it's pronounced the same as 'fausse folle'. Fausse means 'fake' or 'false', and folle means both a 'crazy woman' and a 'drag-queen' or 'ladyboy'.

Adamantane

This molecule always brings a smile to the lips of undergrads when they first hear its name, especially in the UK. For those not in the know, Adam Ant was an English pop star in the early 1980's famous for silly songs and strange make-up.

Bastardane

This is actually a close relative of adamantane, and its proper name is ethano-bridged noradamantane. However because it had the unusual ethano bridge, and was therefore a variation from the standard types of structure found in the field of hydrocarbon cage rearrangements, it came to be known as bastardane - the "unwanted child".

[A. Nickon and E.F. Silversmith, 'Organic Chemistry: The Name Game', Pergamon, 1987].Buckminster Fullerene

This is the famous soccerball-shaped molecule that won its discoverers the Nobel prize for Chemistry in 1996. It is named after the architect Buckminster Fuller who designed the geodesic dome exhibited at Expo '67 in Montreal, from which Sir Harry Kroto got the idea how 60 Carbon atoms could be arranged in a perfectly symmetrical fashion. Because the name of the molecule is a bit of a mouthful, it is often

referred to just as a Bucky Ball. It's also known as 'Footballene' by some researchers. In fact, there is now a whole 'fullerene zoo', with oddly coined names, including: Buckybabies (C32, C44, C50, C58), Rugby Ball (C70), Giant Fullerenes (C240, C540, C960), Russian Egg or Bucky Onions (balls within balls), Fuzzyball (C60H60), Bunnyball (C60(OsO4)(4-t-Butylpyridine)2), Platinum-Burr Ball ({[(C2H5)3P]2Pt}6C60) and Hetero-fullerenes (in which some Cs are replaced by other atoms).There is also a fullerene paper in which the authors describe a method for severing two adjacent bonds in C60, entitled "There Is a Hole in My Bucky" [J. Am. Chem. Soc., 117 (1995) 7003].

Thanks to A. Haymet for the info regarding footballene, and to Charles Turner for the names of the other fullerenes which came from: 'Fullerenes', by Robert F. Curl and Richard E. Smalley, Scientific American October 1991, and to Tom Hawkins for the JACS reference.

Megaphone

Despite having a ridiculous name, the molecule is quite ordinary. It gets its name from being both a constituent of Aniba Megaphylla roots and a ketone.

[S.M. Kupchan et al, 'J.Org.Chem.', 43 (1987) 586].Munchnones

No, these aren't the favourite compound of the Munchkins from The Wizard of Oz, but are in fact a type of mesoionic compound. These are ring structures in which the positive and negative charge are delocalised, and which cannot be represented satisfactorily by any one polar structure. They got their name when Huisgen called them after the city Munich (München), after similar compounds were called sydnones after Sydney.

Huisgen et al. Chem. Ber. 1970, 103, 2611. Thanks to Matthew J. Dowd, Virginia Commonwealth University, Richmond, VA, for supplying this one.

Unununium

I know this is technically an element, not a molecule, but it had such a ridiculous name I thought I'd include it. This is actually element number 111, and was called by the IUPAC temporary systematic name of unununium before it was recently renamed roentgenium. This is a pity, because if it formed ring or cage structures, previously we might have ended up with unununium onions...

[See Pure and Appl. Chem. 51 (1979) 381 for the naming scheme]. Thanks to Chris Fellows for info about its new name.

A sample of pyroxmangite, with white pieces of cummingtonite visible toward

the lower left.

Cummingtonite

This mineral must have the silliest name of them all! Its official name is magnesium iron silicate hydroxide, and it has the formula (Mg,Fe)7Si8O22(OH)2. It got its name from the locality where it was first found, Cummington, Massachusetts, USA.

Putrescine, Cadaverine, Spermine and Spermidine

Putrescine originates in putrefying and rotting flesh, and is quite literally, the smell of death. It is one of the breakdown products of some of the amino-acids found in animals, including humans. Although the molecule is a poisonous solid, as flesh decays the vapour pressure of the putrescine it contains becomes sufficiently large to allow its disgusting odour to be detected. It is usually accompanied by cadaverine (named after the cadavers that give rise to it), a poisonous syrupy liquid with an equally disgusting smell. Putrescine and cadaverine also contribute towards the smells of some living processes. Since they are both poisonous, the body normally excretes them in whatever way is quickest and most convenient. For example, the odour of bad breath and urine are 'enriched' by the presence of these molecules, as is the 'fishy' smell of the discharge from the female medical condition bacterial vaginosis. Putrescine and cadaverine also contribute to the distinctive smell of semen, which also contains the related molecules spermine and spermidine.

Thanks to Bill Longman for suggesting spermine and spermidine, and to Dr Chris Valentine for the info about bacterial vaginosis.Moronic Acid

This is a triterpenoid organic acid that is found in Pistacia resin, and is therefore of interest to people studying archaeological relics, shipwrecks and the contents of ancient Egyptian jars. But why it's called moronic acid is still unknown... Derivatives of this are called moronates, as in 'which moron-ate the contents of this jar?'

Curious Chloride and Titanic Chloride

The trivial name for some curium compounds can be either curous or 'curious', so curium trichloride becomes curious chloride. However the only curious property it has is that it's sufficiently radioactive that a solution, if concentrated enough, will boil spontaneously after a while. (I wonder if a molecule with 2 Cm atoms in would be 'bi-curious'...?)In a similar way, titanium compounds can be 'titanic', so we get the wonderfully named titanic chloride, TiCl4. It's also interesting to know that in the titanium industry, TiCl4 is known as 'tickle'. Furthermore, curium oxides are called 'curates', so the titanium compound would be Titanic Curate, and since curium can have more than one valency we could end up with Curious Curates. But I'm sure these are already a well-known phenomenon...In a similar way, some nickel compounds can be referred to as 'nickelous' - so we get compounds like Nickelous Sulfate (a nice guy by all accounts...)

Fukalite

This wonderfully named mineral gets its name from the Fuka mine in the Fuka region of southern Japan. It is very rare, and is a form of calcium silico-carbonate, with formula Ca4Si2O6(CO3)(OH,F) 2.

More details from: Henmi, C., Kusachi, I., Kawahara, A., and Henmi, K., Mineral. J., 8, (1977) 374. Thanks to Matthew Latto for info on this mineral.

Traumatic Acid

This is a plant hormone which causes injured cells to divide and help repair the trauma - hence its name, and its synonym 'wound hormone'.

Thanks to Dr Neil Edwards of Sussex University for supplying this one, and to Han Wermaat in the Dutch Chemistry magazine 'Chemisch2weekblad' for its information.

Arabitol

No, this has nothing to do with rabbits - it's an organic alcohol that's one constituent of wine. It's also known as pentahydric alcohol. A related sugar molecule, arabinose, also has nothing to do with rabbits, nor with the size of a Rabbi's nose (A Rabbi Nose).

Thanks to David Brady for supplying this arabitol, and to Darren Sydenham for arabinose.Fucitol

Although this sounds like what an undergraduate chemist might exclaim when their synthesis goes wrong, it's actually an alcohol, whose other names are L-fuc-ol or 1-deoxy-D-galactitol. It gets its wonderful trivial name from the fact that it is derived from the sugar fucose, which comes from a seaweed found in the North Atlantic called Bladderwrack whose latin name is Fucus vesiculosis. Interestingly, there are a few articles in the Journal of Biochemistry throughout 1997 concerning a kinase enzyme which acts on fucose. The creators of these articles were Japanese, and seemed to have missed the fact that fucose kinase should not be abbreviated as 'fuc-K'. Similarly, the E. coli K-12 Gene has other proteins that have been named Fuc-U and Fuc-R.

Erotic Acid

No, this isn't the world's best aphrodisiac. Its correct name is orotic acid, but it has been misspelt so often in the chemical literature that it is also known as erotic acid! Another name for it is vitamin B13. Apparently, if you add another carbon to it, it becomes homo-erotic acid...

Thanks to Gerard J. Kleywegt of Uppsala University for info on this molecule.Kinoshitalite

Although it sounds like the trade name of a laxative, this is a type of mica found in Japan and Sweden, and has the formula (Ba,K)(Mg,Mn)3Si2Al2O10(OH) 2. It is green and vitreous, and is about as hard as fingernails, apparently. Its name comes from the Japanese for "under the tree" (ki = tree; no = possessive particle; shita = under).

Thanks to Van King for info on this mineral and Melita Rowley for the Japanese translation.

2 layers of dickite.

Dickite

Dickite, Al2Si2O5(OH)4, is a (kaolin) clay-like mineral which exhibits mica-like layers with silicate sheets of 6-membered rings bonded to aluminium oxide/hydroxide layers. Dickite is used in ceramics, as paint filler, rubber, plastics and glossy paper. It got its name from the geologist that discovered it around the 1890s, Dr. W. Thomas Dick, of Lanarkshire, Scotland.

Structure from the Virtual Museum of Minerals and Molecules

Bastadin-5

This is just one of a number of bastadins, which are molecules isolated from the marine sponge Ianthella basta. They possess antibacterial, cytotoxic and anti-inflammatory properties.

Thanks to Neil Edwards for info on this molecule.

Vomicine

This poisonous molecule gets its name from the nut Nux Vomica, which is the seed of a tree found on the coasts of the East Indies. The seeds are sometimes called 'Quaker buttons', and are a source of strychnine as well as the emetic vomicine.

Thanks to Bill Longman and Alan Howard Martin for info on this molecule.

Rhamnose

This sounds like the molecule that's created when you walk into doors...in fact it's a type of sugar.

Thanks to Bill Longman for info on this molecule.

Gossypol

This ridiculously named molecule is found in cotton seeds. It was used as a male contraceptive in China, but was never used in the West (and may have since been banned in China as well), since its effects were permanent in about 20% of patients! Its name originated from being present in the flowers of the Indian cotton plant Gossypium herbaceum L. Apart from its contraceptive effects, gossypol has properties that might make it useful in treating a number of ailments, including cancer, HIV, malaria and some bacterial/viral illnessness. Related to this molecule are the equally strangely named gossypetin and gossypin. I always thought 'gossypin' was frowned upon in polite labs...

Thanks to Lionel Hill for suggesting this molecule, and to Anthony Argyriou and Kristina Turner for providing some of the info.

Skatole

This molecule's name comes from 'skatalogical', meaning concerning fecal material. Its proper name is 3-methylindole, but it gets its trivial name from the fact that it is a component of feces. Surprisingly, it is also found in coal tar and beetroot (!), and can be obtained synthetically by mixing egg albumin and KOH. As you might guess, skatole consists of white to brownish scales which are soluble in hot water. Apparently, coriander can be used to cover up bad smells such as these, as testified in the classic paper: "Deodorizing Effect of Coriander on the Offensive Odor of the Porcine Large Intestine" [Kohara et al, Food Sci. Technol. Res. 12 (2006) 38.]

Thanks to Allen Knutson for suggesting this molecule, and to Samuel Knight for providing the info.

Arsenolite

This is a naturally occurring mineral, whose correct name is cubic arsenic trioxide (As2O3). It is also the primary product whenever arsenic ores are smelted, and is used in industry as a glass decolourising agent. Another related mineral with a similar silly name is arsenolamprite, which is a native form of arsenic.

Thanks to Matthew Latto and Nicholas Welham for suggesting these minerals.Sexithiophene

This is a 'sexi' molecule - which means it has 6 sub-units, in this case of thiophene rings. Because of its conjugated system of double bonds, this organic molecule conducts electricity quite well. As a result, it is one of a number of similar molecules being studied for possible uses in organic polymer electronics. Incidentally, the Latin for 5 sub-units is quinque (pronounced 'kinky'), so by adding one subunit a quinque molecule becomes sexi... Nine units would be nonakis...which shows what always happens if you try to take things too far.

Bis(pinacolato)diboron

Although it sounds like it, this isn't the active ingredient in a pina colada cocktail. Rather it is a versatile reagent for the preparation of boronic esters from halides, the diboration of olefins, and solid-phase Suzuki coupling. See, for example J.Org. Chem. 60 (1995) 7508. A proper Pina Colada cocktail is a concoction of pineapple juice, coconut milk and rum, often served with crushed ice and a little paper umbrella stuck in the glass.

Thanks to Victoria Barclay of Advanced Chemistry Development, Inc., Toronto, for providing the info on this molecule.

Lucifer yellow

I think Lucifer Yellow is a food colouring used especially in hot sauces, like salsa pickle. It is also used in plant microscopy anatomy studies, because it fluoresces under ultraviolet light and stains certain regions between plant cells.

For more info, see here. Thanks to Gavin Shear of Advanced Chemistry Development, Inc., Toronto, and to Seranne Howis, of Rhodes University, South Africa, for providing the info on this molecule.

Crapinon

Crapinon (also known as Sanzen) is another molecule with an excellent name, and is apparently used therapeutically as an anticholinergic. These are drugs which dry secretions, increase heart rate, and decrease lung constriction. More importantly, they also constipate quite strongly - so 'crappy-non' is most appropriate. It would be nice to think that this molecule could find an alternative use as a toilet cleaner (as in "Who's been crapinon the seat?").

Thanks to Gavin Shear of Advanced Chemistry Development, Inc., Toronto, and Tom Simpson of the Royal Hobart Hospital, Austalia for providing the info on this molecule.

Sparassol

This molecule sounds like what you'd need the day after eating a very hot curry (spare-assol). Sparassol is an antibiotic produced by the fungus Sparassis ramosa.

Thanks to Eric Walters from The Chicago Medical School for providing the info on this molecule.

Periodic Acid

Ok, I know it should really be per-iodic acid, but without the hyphen it sounds like it only works some of the time...It has also been described as that acid extracted by boiling of old periodic tables found in chemistry lecture halls and laboratories.

Thanks to Allen Knutson for suggesting this molecule, and to Prof Walter Maya of California State Polytechnic University for some of the details.

Phthalic Acid

This molecule is often pronounced with a silent 'th' for comic effect. I wonder if phthalyl side-groups have a shorthand symbol in chemical structures, in the same way that phenyl groups are shortened to -Ph? If so, would it be a 'phthalic symbol'...?Again, adding an extra carbon makes homo-phthalic acid - say no more...

Thanks to Neil Edwards of Sussex University for info about this molecule.

Psicose

This molecule has nothing to do with axe-murderers, but is a sugar which gets its name because it's isolated from the antibiotic psicofurania. Its other name is ribo-hexulose.

Commic Acid

This molecule's always good for a laugh! It gets its 'commical' name since it's a constituent of the plant Commiphora pyracanthoides, one of the Myrrh trees. When reduced to the aldehyde, I presume the product would be named commical?

Thanks to Michael F Aldersleyfor info about this molecule.

Fruticolone

This sounds like what you get after a baked bean meal...but it actually gets its name from being both a constituent of the plant Teucrium fruiticans and a ketone.

Nonanone

Although maybe not quite as silly as some of the other molecular names, I like this one for its n-n-nice alliteration. Many nonanones act as alarm pheremones in wasps, ants and bees. Interestingly, in Danish, Norwegian, Swedish and German molecular names are spelt without the end "e" (e.g. butane is butan, etc.). Therefore nonanone becomes 'nonanon', and is quite an exceptional molecule name, being spelled the same way forwards and

backwards - a palindromic molecule! The molecule shown is 2-nonanone, but 5-nonanone with the C=O group in the middle would be the same forward as well as backwards, thus being palindromic in spelling and in structure!

Thanks to Carl Kemnitz for supplying some info about this molecule.

Fukugetin

This chemical with a most amusing name is also called Morellofavone, and is a constituent of the bark of the Garcenia species of tree. Its glucoside goes by the equally wonderful name of Fukugiside.

Pubescine

Also known as Reserpinine. It got its name since it was extracted from the plant Vinca pubescens. I don't know much else about pubescine, but I bet it forms short, curly crystals...

Thanks to Michael J. Mealy of the University of Conneticut and to ShadowFox for providing the info on this molecule.

Spamol

Monty Python's favourite molecule? Spamol might also conjure images of unwanted "Make Money Fast" emails circulating the globe at the speed of light ("spam - all"). Its other names are aminopromazine, lispamol or lorusil, and it's actually used as an anti-spasmodic therapeutic agent.

Thanks to Victoria Barclay of Advanced Chemistry Development, Inc., Toronto, for providing the info on this molecule.

Fukiic Acid

Fuki is the Japanese word for the butterbur flower, and Fukiic acid is the hydrolysis product from this plant, Petasites japonicus. Interestingly, further oxidation of this produces the wonderfully named Fukinolic acid. (I wonder if fukanolic is anything like alcoholic...) Anyway, since the conjugate base of fukinolic acid is fukinolate, it's probably about time we stopped!

Thanks to Anton Sherwood for info on fukiic acid, and to Andrew Reinders for suggesting fukinolate.

Funicone

This gets its name, not from being funny and cone shaped, but because it's the metabolism product of the fungus Penicillium funiculosum.

Housane, Churchane and Basketane

Obviously, these molecules get their name from their shapes. Although I do think that housane (how sane?) should be closely linked to psicose, above.

Thanks to A. Rich for suggesting these molecules.Windowpane

Windowpane C9H12 gets its name from its resemblance to a set of windows, and is more accurately kown as fenestrane. But unfortunately it has never been synthesised. However, the version with a corner carbon missing C8H12 has been made, and goes by the name 'broken window'. Interestingly, a hypothetical derivative of windowpane has been suggested which includes a double bond, and this would of course be called Windowlene...

Thanks to Adrian Davis of Pfizer Global Research & Development for providing the info on these molecules, and to Iain Fenton for suggesting windowlene.

Godnose

Ok, so this is a bit of a cheat, since it's not an official molecular name...but it makes a nice story. When Albert Szent-Gyorgyi isolated ascorbic acid and published his findings, he called the new substance 'ignose' since he was convinced it was a sugar that resembled glucose and fructose, but was ignorant of its structure. When the journal editor refused to accept ignose as a sensible name, Szent-Gyorgyi suggested 'Godnose' instead! Alas the editor was neither imaginative nor humorous, and suggested that a more proper name had to be used. The structure of the carbohydrate was elucidated in collaboration with Haworth at Birmingham and the alternative name given was hexuronic acid (hex = six). During the same period (1928–1931), Charles Glen King of the Columbia University of USA isolated Vitamin C from lemon juice and it was observed that hexuronic acid and Vitamin C were identical. Szent-Györgyi documents the episode in the essay "Lost in the Twentieth Century," which is in Volume 32 of the Annual Review of Biochemistry, and dates from 1963.

Thanks to John P Oliver, Peter Macinnis and Charles Turner for providing the info and story. Incidentally, Godnose is also the name of an Australian punk band.Luciferase

This molecule is an enzyme which reacts with ATP to cleave luciferin, its substrate. This cleavage reaction causes the firey glow in fireflies and certain types of fish, hence its name.

Thanks to Melissa Harrison for suggesting this molecule.

Diabolic Acid

Diabolic acids are actually a class of compounds where the m and n chains can have different lengths and can contain unsaturation. They were named after the Greek diabollo, meaning to mislead, since they were particularly difficult to isolate using standard gas chromatography techniques. One of the inventors, Prof Klein, also thought that they had 'horns like the devil'.

Domperidone

This molecule sounds like it should be the active ingredient in Dom Perignon champagne, but it's actually an anti-emetic drug. It is also used to promote the production of breast milk in lactating (or non lactating women). It's also been used to induce lactation in a male!

Gardenin

If you fancy a bit of gardenin', this is the molecule for you. In fact, these are many different gardenins, which are flavones extracted from Gardenia lucida, a plant from India. The structure left is for gardenin A, which forms yellow crystals.

Thanks to Eric Walters from The Chicago Medical School for suggesting this molecule. Ref: A.V.R. Rao, et al, Indian J. Chem. 8 (1970) 398.

Germane

This is a particularly relevant molecule that is pertinent and has a bearing on a number of inorganic reactions...

Thanks to Eric Walters from The Chicago Medical School for suggesting this molecule.Uranate

The various uranium oxide anions (UO22-, UO3

2-, UO42-, etc) go by the glorious name of 'uranates'. I wonder if unwanted

reactions of these ions with certain compounds is called 'involuntary uranation'...? And is nickel uranate what you'd need to 'spend a penny'?Related to this, uranium nitrate is also known as uranyl nitrate, which sounds like the entry fee for a gents toilet after 8pm...

Thanks to Victor Sussman from Carleton College in Northfield, MN, USA for suggesting this molecule, and to Amy

Roediger for suggesting nickel uranate.

Kunzite (Spodumene)

This mineral is a pink (of course...) gemstone, named after the gemologist G.F. Kunz who described it in 1902. Kunzite is a fragile stone, which shows different shades of colour when viewed from different directions. Called an "evening" stone, it should not be exposed to direct sunlight which can fade its color in time. Its alternative name, Spodumene, sounds like an American shop that sells computer nerds ("Spod-U-Mean")

Conantokin

This chemical sounds like Conan the Barbarian has been smoking something he shouldn't... In fact it's a peptide neurotoxin found in the marine snail Conus geographus. Researchers have found that some conantokins cause young mice to fall asleep, and older mice to become hyperactive, but they don't say what happens to middle-aged mice...It probably gets its name because it was isolated from Conus snails hence "con-". And, "antok" is a Filipino word which means "sleepy", which refers to its effect on young mice. Apparently, there is also a related molecule called "contulakin". "Tulak" is a Filipino term for "push". It seems that this molecule causes mice to be sluggish and thus, they had to be pushed.

Thanks to Dr. Andrew P. Rodenhiser from McGill University, Canada, for suggesting this molecule, and to Jesper Karlsson of the University of Kalmar, Sweden, and Rene Angelo Macahig of Ateneo de Manila University, Philipines, for more info about it.

Welshite

This wonderfully named mineral is called after the US amateur mineralogist Wilfred R. Welsh. Its formula is Ca2SbMg4FeBe2Si4O20. Some people think it's quite a nice mineral, but others think it's 'well-shite'.

Thanks to Matthew Latto for suggesting this mineral.Propellane and Cubane

These two molecules are both named after their distinctive shapes. Propellane (left), C5H6, resembles a propeller, whereas cubane (right), C8H8, is a cube (but doesn't come from Cuba). Other molecules that get their name from their geometric shapes are: dodecahedrane C20H20, prismane C6H6, spherands and hemispherands, squaric acid C4H2O4 and deltic acid C3H2O3, tetrahedranes C4H4 and C20H36 and finally twistane C10H16.

Thanks to Kay Brower for suggesting propellane, and to Martin A. Iglesias Arteaga from the University of Havana, Cuba for suggesting cubane. Thanks also to Mark Minton for suggesting the other list of geometrical molecules. First reference for propellane: J. Altman , E. Babad, J. Itzchaki, D. Ginsburg , Tetrahedron, Suppl. 8(1), (1966) 279.

Clitoriacetal

This gets its name from the root of the Clitoria macrophylla plant, and is a constituent of the Thai drug "Non-tai-yak" which is used to treat respiratory disorders, including pulmonary tuberculosis and bronchitis, and also works as an insecticide.

Vaginatin

I know you can get most things nowadays in a tin, but this is getting silly... Actually it gets its name from the plant Selinum Vaginatum. The related molecule is Vaginol, which also goes by the name Archangelicin.

Thanks to Matti.Lepisto and Stephen Yabut for the info on this molecule.

Anol

Anol is a synonym for 4-(1-propenyl)phenol, and it is apparently used in the flavour industry. Are compounds that bond strongly to this molecule called 'anolly retentive'?

Urospermal

The European Union has standardised everything else (apple sizes, the shapes of bananas, etc...) and it now sounds like they're going even further (Euro-sperm-all). In reality, it gets its name from being a constituent of the roots of the Urospermum delachampii plant.

Buccalin

This sounds like the molecule from which car seat-belts are made, but it's actually a neuropeptide which acts in nerves to stop acetylcholine release.

Thanks to Dr. Andrew P. Rodenhiser from McGill University, Canada, for suggesting this molecule.

Antipain

Antipain is a protease inhibitor, which means it prevents proteins from being degraded. Despite its promising name, it is a very toxic compound, and it causes severe itch or pain (!) when contacted with the skin. Its name is actually a contraction of anti-papain, since it inhibits the action of papain, an enzyme found in papayas.

Thanks to Marcel Volker from Leiden University Medical Center, Netherlands, for suggesting this molecule.

Dinile

Why did the two cyanide groups go to see a psychiatrist? Because they were both 'in dinile'... In fact, dinile is another name for butanedinitrile or succinonitrile, and is a waxy solid that if ingested forms cyanides in the body.

Thanks to Hazel Mottram and Phil van Ess for suggesting this molecule.

Fornacite

This is a mineral that is composed of a basic chromate-arsenate compound of Pb and Cu with the formula: (Pb,Cu2+)3[(Cr,As)O4]2(OH). If it could be polished into a gemstone, it sounds ideal for a ring that a cheating husband might buy his mistress.

Thanks to Alan Plante, a New Hampshire, USA, "Rockhound", for suggesting this mineral.

The dark lumpy bits on the white background are Fornacite

Butanal

This molecule sounds better if it's hyphenated (but-anal), but it is actually quite a common aldehyde.

Thanks to Shawn McClements, Amsterdam NY, USA, and his high school class for suggesting this molecule.

Angelic Acid

Angelic acid isn't very angelic at all - it's a defence substance for certain beetles. It gets its name from the Swedish plant Garden Angelica (Archangelica officinalis) from whose roots it was first obtained in the 1840s. Its proper name is (Z)-2-methyl-2-butenoic acid. The other isomer (E) goes by the equally silly name of tiglic acid (from the plant Croton tiglium, the source of croton oil) and is also a beetle defence substance.

Thanks to Andrew Walden for suggesting these molecules and to Florian Raab and Bo Ohlson for providing some of the information about them.

Ciglitizone

This molecule sounds like the places reserved for smokers to light up. Actually, ciglitizone is is a member of a class of compounds that are used as anti-diabetics. The drug Avandia (Rosiglitazone), used to treat type II diabetes, is a member of this class of compounds. Another related molecule is troglitazone, which I've mentioned for all fans of the eponymous rock group or small cave dwelling dwarfs.

Thanks to Robin Brown of Galapagos Genomics, Belgium, and to Joerg Fruechtel for the info on this molecule. (More info, see: Br. J. Pharmacol. 131 (2000) 651).

Clitorin

I don't know much about clitorin, except that it's a flavenol glycoside (make of that what you will), but I've heard it's touch sensitive ;-).

Thanks to Joerg Fruechtel and Nicholas J. Welham for the info on this molecule. (More info, see: Phytochemistry 55 (2000) 67).

Constipatic Acid

This is a constituent of some Australian lichens, but I don't know how it got its name. Derivatives of this are protoconstipatic acid, dehydroconstipatic acid, and methyl constipatate.

See D.O. Chester and J.A. Elix, Austr. J. Chem. 32 (1979) 2565. Thanks to Ronald Wysocki of the University of Arizona for suggesting this molecule.

Fucol

This sugar sounds like it doesn't do very much! Actually the L-Fucol form is obtained from the eggs of sea urchins, frog spawn and milk. The L-fucol form also goes by the name of rhodeose.

Thanks to Ronald Wysocki of the University of Arizona for suggesting this molecule.

Penguinone

This gets its name from the similarity of its 2D structure to a penguin. The effect is slightly lost in the 3D model, though. It's real name is: 3,4,4,5-tetramethylcyclohexa-2,5-dienone.

Thanks to Chris Scotton for suggesting this molecule.Ovalene

Ovalene is a polycyclic aromatic hydrocarbon, C32H14. Funnily enough it's oval-shaped... In the series of polycyclic aromatic hydrocarbons to which ovalene belongs, the next one is circumanthracene...(is it also known as oy-vane?).

Thanks to Terry Frankcomb of the University of Queensland, Australia for suggesting this molecule, and to Professor Juan Murgich of the Venezuelan Institute for Scientific Research, Caracas, for providing a correct structure.

Aenigmatite

This mineral gets its 'enigmatic' name from the fact that its chemical composition was originally difficult to determine. It is an iron and titanium silicate with sodium as a charge balancing cation, although because it does not easily fit into the current classification system, it is classified as an 'Unclassified Silicate'.

Thanks to Phillip Barak of the Virtual Museum of Minerals and Molecules for suggesting this mineral.

Dogcollarane

Dogcollaranes are a group of molecules made from alternating bicyclo [2,2,0] and norbornyl segments. When there are 24 such components, the ends can be linked together to form a ring, which looks like a dogcollar. Unfortunately, although many of the intermediate structures have been made, none of the dogcollaranes have yet been synthesised.

For more info, see: Aust. J. Chem. 40 (1987) 1951.Thanks to John Lambert of the University of Melbourne for suggesting this molecule.

Fuchsite

Fuchsite is a mineral, and is the green form of Muscovite, KAl2(AlSi3O10)(F, OH)2. It is used as an ornamental stone, and apparently has perfect cleavage...

Thanks to Tanuki for suggesting this mineral.

Sepulchrate and Sarcophagene

These spooky sounding molecules both have structures which wrap around and enclose metal atoms, such as cobalt, in a coffin-like cage. Hence their names.

Thanks to Mark Minton for suggesting this molecule.

Pagodane

This C20H20 molecule gets its name because it resembles a Japanese pagoda - well, two pagodas, back-to-back.

Thanks to Mark Minton for suggesting this molecule.

DEAD

DEAD is actually the acronym for diethyl azodicarboxylate, which is an important reagent in the well-known Mitsunobu reaction which performs a stereospecific conversion of an alcohol to a primary amine. It's quite a good acronym, as DEAD is an orange liquid that's explosive, shock sensitive, light sensitive, toxic, a possible carcinogen or mutagen, and an eye, skin and respiratory irritant! A version of diethyl azodicarboxylate mixed with acid and triphenylphosphine has also been termed DEADCAT.

Apatite

A mineral for hungry people? Apatite is a phosphate mineral with the composition Ca5[PO4]3(OH,F,Cl). It has been used extensively as a phosphorus fertilizer and is still mined for that purpose today. The mineral called "asparagus stone" is a appropriately a type of green apatite. Ironically, apatite is the mineral that makes up the teeth in all vertebrate animals as well as their bones.

Thanks to 'Sparkly' Sally Ewen for suggesting this molecule and to Sean and to Kay Dekker for some info about it.

Lepidopterene or Biplanene

Lepidopterenes are a whole class of molecules named after their structural similarity to a butterfly. When the two wings are directly over one another, they look like a WW1 biplane, and so this group of molecules has been termed 'biplanenes'.

Thanks to Mark Minton for suggesting this molecule.Snoutene

This strange looking molecule resembles the nose or snout of an animal, but I don't know if it smells...

Thanks to Mark Minton for suggesting this molecule.Crown Ethers and Lariat Ethers

Both these molecules get their names from their distinctive shapes. Crown ethers look like crowns (shown in red in the picture on the right), whereas lariat ethers look like lassos, and are really just crown ethers with extended 'tails' (shown in blue). Some lariat ethers are so flexible that they can stick their tails into their rings (nice trick!), and so have been termed 'ostrich complexes', or 'tail biters'. Lariat ethers with two tails are called 'bibrachial lariat ethers' (bracchium means 'arm'), and are abbreviated as BiBLEs.

Thanks to Mark Minton for suggesting this molecule.Cacodyl

This molecule gets its name from the Greek kakodes, meaning 'stinking', as it has a really pungent smell of manure with a delicate hint of garlic. It is sometimes spelled 'kakodyl', but its correct name is tetramethyl diarsenic. Its main claim to fame is that it was one of the compounds worked on by Bunsen (of burner fame).

Thanks to Birgit Schulz for suggesting this molecule and to Lars Finsen for correcting the spelling of the name.

Betweenanene (Screwene)

Betweenanenes are molecules which have a trans double bond shared between two cycloalkanes. There is a whole family of them, depending upon the size of each ring. The one shown on the right is the [10,10] betweenanene. If there are two double bonds linked together, the molecules are called screwenes, but this terminology isn't that popular, for obvious reasons!

More info see: J. Am. Chem. Soc. 99 (1977) 3508.Thanks to Mark Minton for suggesting this molecule.

Paddlane

Paddlanes are molecules which have bicyclic cyclohexane units, which look a bit like the paddles on Mississippi steamboats.

Thanks to Mark Minton for suggesting this molecule.

Furfuryl Furfurate

A ridiculously-named molecule, about which I know virtually nothing, although I'm told it's quite smelly and may be used as a vapour phase polymerisation inhibitor. It got its name from the Latin "furfur", meaning "bran" (the source of the compound). A related molecule, furfural alcohol is apparently used in the fabrication process of the Reinforced Carbon-Carbon (RCC) sections used in the space shuttle.

Thanks to Steve Colley for suggesting this molecule, and to Calli Arcale and Ogpusatan and Danny Sichel for info about it.

Carnallite

Carnallite is KMgCl3·6H2O, an evaporite mineral. Surprisingly for a mineral called carnallite, it doesn't exhibit any cleavage... It's used as an ore for potassium fertilizers, and is named after Rudolf von Carnall, a Prussian mining engineer, whose knowledge of the subject was famous...

Thanks to Phillip Barak of the Virtual Museum of Minerals and Molecules for suggesting this mineral.

Draculin

Draculin is the anticoagulant factor in vampire bat saliva. It is a large glycoprotein made from a sequence of 411 amino acidsbeen able to find a picture of it yet.

Thanks to Mark Baxter for suggesting this molecule and to Eric Walters for some of the info about it.Rudolphomycin and Rednose

Rudolphomycin is a antitumor antibiotic compound. It was named following a series of such molecules derived from 'bohemic acid' - which was given its name because the discoverer Dr Nettleton was an avid opera fan and called it after the Puccini opera La Bohème. Derivatives of this were then given names from characters in the opera, such as mussettamycin and marcellomycin, after Musetta and Marcello, and rudolphomycin after the character Rudolph. On degradation of rudolphomycin, a new sugar was obtained, which was christened 'rednose'. This rather silly name was probably allowed to stand

since the paper was submitted on December 21st 1978, and the journal editor probably had the Yuletide spirit!

Thanks to Janet McBride for suggesting these Christmas-ey molecules.

George and Bi-George

The story goes that when undergraduate James Carnahan achieved the synthesis of a new cage structure at Columbia University, he asked his supervisor Prof Katz to suggest a name for it. Since trivial names are often arbitrary, he suggested 'George'. When George was heated with a Rh catalyst, it dimerised to produce Bi-George!

Eurekamic Acid

Eureka! was supposedly the exclamation used by Archimedes when he found something interesting in his bath water. It means 'I have found it', and so when researchers at May and Baker discovered this acid, they felt it was such a 'Eureka moment' that they named the molecule after it.

Catherine

I don't know much about this molecule except that its name comes from the plant Catharanthus roseus. I'm surprised, though, that it's not wheel shaped...

Complicatic Acid

This molecule didn't get its name because it was complicated to make, rather from the plant Stereum complicatum from which it was isolated.

Ptelefolone

This molecule rings a bell...It gets its name from the hop tree Ptelea trifoliata, but I don't know much else about it.

Pterodactyladiene

This is a group of molecules that resemble the ancient flying reptiles. The R groups can be altered to give different sized 'heads' or 'tails'.

Thanks to Ewart Shaw for suggesting this molecule.Miazole and Urazole

If you pronounce the 'a' as in 'cat', and the 'z' as an 's', then you get the classic chemistry joke: What's the difference between miazole and urazole? The size of the ring...And shouldn't there be a 'herazole', a 'theirazole' and an 'ourazole' to get a complete bunch of azoles? Actually, the proper name for miazole is imidazol, but that spoils the joke a bit....

Thanks to Steve Stinson for suggesting these molecules.Ethyl Lactate

This is another standard undergraduate chemistry joke, based around the fact that Ethyl sounds like a common female name. "How do you make Ethyl lactate...?" Other names involving "Ethyl" such as Ethyl palpitate, Ethyl fornicate and the spinster Ethyl celibate also make good jokes, but unfortunately the corresponding acids (palpitic, fornic and celibatic) are unknown. In a similar vein, is copper tartrate what's paid to policewomen who are impersonating prostitures?

Thanks to John Figueras for suggesting this molecule and to Suds Mixer for info about it, and Colin Metcalf and to Peter Rice for the ethyl celibate and tartrate jokes, respectively.

Cristane

So what's so amusing about cristane? Well, for the non-biologists amongst you, a 'crissum' is the name given to the anus of a bird! Tricyclo[5.3.0.0]decane, was nicknamed cristane since on the evening it was first discovered in Brown University, someone left the window open. A pigeon got into the lab overnight and did what pigeons do - all over the lab and equipment. The clean-up crew named the new molecule in honour of the part of the bird's anatomy that had provided the 'surprisingly abundant gift'.

Birdcage

This molecule is so called because it, um, resembles a birdcage, duh. Maybe it should have been used to capture the aberrant pigeon from cristane, above...

Apolloane and Rocketene

Apolloane was created at the same time as the Apollo 11 moon landings. When drawn as a flat diagram the structure bears a striking similarity to a rocket, with side fins and exhaust. And the OH is even located at carbon 11, to get apolloane-11-ol. Apparently, Neil Armstrong's personal memorabilia include a reprint of the chemistry publication which named it: [A. Nickon, et al., J. Am. Chem. Soc. 92 (1970) 1688.]On a similar theme, Rocketene was also named for its structural resemblance to a rocket.

Thanks to Jarrod Ward for suggesting this molecule.

Manxane and Manxine

Manxane resembles the coat of arms of the Isle of Man (called a triskelion) which consists of 3 armoured legs in a circle. Bicyclo[3.3.3]undecane was named Manxane since it closely resembles this Manx emblem. Later on, a group of researchers at the University of Illinois created an analog of Maxane with a bridgehead nitrogen, and so called it Manxine. Professor Leonard, who created this molecule, thought Manxine sounded like a girl's name - so we now have the male (manxane) and female (manxine) versions of the molecule, with the difference being what is situated between their legs!

Cornerstone

Ok, this is a bit of a cheat, since its real name is b-corrnorsterone, but it's known as 'cornerstone' by all those that work with it. It got its name since it's a ketone with a norsteroid structure (hence 'norsterone') and the discoverer, Robert Woodward at Harvard, thought it might eventually be possible to transform it into a corrinoid.

Adamsite

This molecule was named after the renowned chemist Roger Adams of the University of Illinois. It's actually a chemical warfare agent, and is 'a damn sight' better at killing people than most other molecules...

BON-BONs

These ring structures are not what makes French sweets taste sweet. Heterocyclic dimers like the one shown in the picture (where you vary the R, R' and R" groups) are named from the fact that the ring atoms in sequence spell out BON-BON.

Performic Acid

An actor's favourite chemical? As you might expect from a per-acid, it's a very strong oxidising agent, and always puts on a great per-formance!

Thanks to Andy Dicks of the University of Toronto, for suggesting this molecule.R-CMP

As anyone from Canada will know, RCMP are the initials for the Royal Canadian Mounted Police, but this molecule isn't their emblem. R-CMP is actually short for R-cytidine monophosphate, and is actually a component of RNA, the nucleic acid which transcribes the genetic information from the DNA so that it can be translated into protein.

Thanks to Amanda Musgrove from the University of Alberta, Canada (of course) for suggesting this molecule.Sonic Hedgehog

Fruitfly genetics has a rich history of 'creative' nomenclature, often based on the appearance of flies that have the gene in a mutated form. One of these mutated genes made fruitfly embryos look like hedgehogs, since their spines grew all over their body rather than just in specific places - so it was name the 'hedgehog' gene. The vertebrate analogue was called 'Sonic' Hedgehog in order to distinguish it from its insect-forming version, and was given the abbreviation Shh. Geneticists studying other organisms are happy to elaborate on this when they can get away with it, and there are other variety of hedgehog genes called Indian hedgehog (Ihh), Desert hedgehog (Dhh), and even 'Tiggy-Winkle hedgehog' (TWhh)! There are also genes called Sleeping Beauty, Tubby, and most recently the puberty gene, "Harry Potter".

Thanks to Greg Valure for suggesting this gene, and to Richard Williams from the Institute of Cancer Research and Geraldine VdA for providing some of the info about it, and to David Bradley for the other gene names. More fruitfly gene names and their stories can be obtained from www.flynome.com, and thanks to Jeremy Bracegirdle for supplying this link.

Gibberelic Acid

Gibberelic acid isn't a psychotropic drug that makes you gibber insanely like a monkey...it's actually one of a number of gibberelins, which are plant hormones which control various aspects of plant growth.

Thanks to Mathias Disney for suggesting this molecule.Darlingine

This molecule is lovingly extracted from the Brown Silky Oak tree, Darlingia darlingiana.. It hasn't been analyzed biologically yet, but may have activities similar to other tropane alkaloids, such as muscle contraction and stimulation...(But it only works if you treat it nicely...)

Thanks to Christopher Wells for info on this molecule.Jesterone

This playful and mischievous molecule is found in a fungus, Pestalotiopsis jesteri, which lives inside yew trees.

Thanks to Christopher Wells for info on this molecule.

Trunkamide

Trunkamide has nothing to do with elephants, although its spacefill structure shown right looks a bit like an elephant. It was isolated from a sea squirt living in the Great Barrier Reef, and is reported to have anti-tumor properties.

Thanks to Christopher Wells for info on this molecule.

Diurea

As you might expect, this molecule and its derivatives are often used as a fertiliser, being splattered liberally around fields of crops. It's also known as biurea, but its proper chemical name is N,N'-dicarbamoylhydrazine. It's also sometimes used as flow improver in paints and greases. So next time you paint your house you can tell people you're covering it with diurea...

Thanks to Gene Morselander for info on this molecule.Parisite

This mineral sounds like it grows on other minerals. It is found in Columbia, and it's named after J. J. Paris, who was a mine proprietor at Muzo, north of Bogota, Columbia. It is a member of the Bastnasite group of complex carbonate-fluoride minerals, and has the formula Ca(Nd,Ce,La)2(CO3)3F2.

Thanks to Tanuki the Raccoon-dog for info on this mineral.Clintonite

This mineral sounds like it should be found in close proximity to 'internite' or 'lewinskyite'..., but it was actually named after American Statesman De Witt Clinton (1769-1828), not the notorious ex-President. Its formula is Ca(Mg,Al)3(Al3Si)O10(OH)2 (a calcium magnesium aluminosilicate hydroxide mineral), and it's related to margarite. It is found abundantly in the northern extent of New York.

Thanks to Friedrich.Menges and Steven A. Hardinger for info on this mineral, and to Hans Hillewaert for the link to the image.

Sodamide

This is the shorthand name given to the common chemical, sodium amide, NaNH2. It sounds like it belongs in close proximity to other molecules in this list, such as arsole, anol, skatole, and maybe fruticolone...But I'm not letting it get anywhere near miazole!

Thanks to Germanicus Hansa-Wilkinson for suggesting this molecule.

dUMP

dUMP is the acronym for 2'-deoxyuridine-5'-monophosphate, and is an RNA transcription subunit - or a bit of the thing that makes proteins, and is one of the building blocks of DNA. dUMP is a deoxygenated form of RUMP, which is another of the bases found in RNA. If you want to have a 3D dump, click on the structure to the left.

Thanks to Christopher Putnam of the Ludwig Institute For Cancer Research, La Jolla, CA, and Peter Traill from the University of Dundee, and John Gosden for info on this molecule.

BARF

There are two molecules that are called by their shorthand name of BARF. The first, often written as BArF, is a halide abstracting reagent B[3,5-(CF3)2C6H3]4

-, i.e. two CF3 groups on each phenyl, and four of those phenyls on a boron. The second is written BARF, and is the shorthand for tripentafluorophenylborane (B-Ar-F), see structure on the right. It is mainly used as a strong Lewis acid to abstract a methyl group in the reaction to make a highly active ethylene polymerization catalyst. So you really can barf into a plastic bag...

Thanks to Ken Weakley for suggesting the second BARF, and to Thomas Vaid at Washington University for the first BArF.

Small-breasted-dog

Yes, it really is called that, but in Spanish! The molecule is actually named 'Perrottetin-a' which (almost) literally means "small-breasted-dog" (Perro=dog, tetita=small breast). The molecule gets its name from the liverwort plant from whence it is extracted, Hepatica Radula perrottetii, but I don't know why the plant is named after a small breasted dog?

Thanks to Enrique Pandolfi for providing the info on this molecule. See: Y. Asakawa, K. Takikawa, M. Toyota, T. Takemoto, Phytochem., 21, (1982) 2481.

Centaureidin

Centaurs are creatures which are half horse, half human. The molecule centaureidin got its name because it was extracted from a flower called Centaurea corcubionensis, which is related to the cornflower. It was discovered along with a molecule named centaurein, found in the same plant.

Thanks to Victoria Barclay from ACD in Toronto and to ShadowFox for providing the info on this molecule. Here is a scientific article about Centaureidin.

Sandwicensin

John Montagu, The Fourth Earl of Sandwich, was a notorious gambler who would often go from pub to pub in London on gambling marathons. To satisfy his hunger while continuing to gamble, he would order slices of meat between two pieces of bread. Thus, was the sandwich born. But how about "Sandwicensin"? As a newly identified cytotoxin, isolated from a soggy old sponge at that, we guess that it must be somewhat less than appetizing!

Thanks to Victoria Barclay from ACD in Toronto for providing the info on this molecule.Magic Acid

'Magic Acid' is the name given to one of the strongest of the inorganic 'superacids'. It is made by mixing together antimony pentafluoride (SbF5) and fluorosulphonic acid (HSO3F), and it is so strong (pKa = -20) that it is capable of protonating even saturated alkanes, like methane, to

produce carbonium ions.

Thanks to Indranil Sen from the Utah State University for suggesting this molecule.Profilactin

Actin is an intracellular fiber protein (best known in muscle contraction), and profilin is a protein that interacts with actin to "promote filament" formation. When profilin and actin are bound together, the complex was originally labelled: "Profilactin", which is most appropriate since it was first isolated in sea urchin sperm. However, I'm told this name was not officially recognised. Also, the first submission of a name for this protein was "screw-in"...because when the filament is ejected from the tip of the sperm, the globular actin shoots outward in a screwlike motion. Although this, too, was a clever name given the protein's location...it was turned down as well. Its official name is now 'the profilin-actin complex'.

Thanks to Blair Boehmer from Duke University, Shefa Gordon at Berkeley and to Leigh Arino de la Rubia for info on this molecule.

Crocidolite

This has nothing to do with crocodiles, but is actually the name of the mineral form of blue asbestos, with formula Na2Fe5Si8O22(OH)2. It either got its name from the Greek word for 'woolly', or it was named from the geographic location of where it was first discovered. viz. the Crocodile River Valley in South Africa. This is just outside Nelspruit in Mpumalanga South Africa (look on the Eastern part of a SA map - next to the Kruger National Game Park).

Thanks to Indranil Sen for suggesting this molecule and to Stuart Kidd and Grant Little for providing some of the information about it.

Bellendine

For non-English readers, I won't tell you what 'bell-end' is slang for, but a clue might be that the molecule is extracted from the flower Bellenda Montana, which should have a purple head...

Piano Stool

These are a group of molecules made from a transition metal bonded to a cyclopentadienyl ligand, so that the resemble a 3-legged piano stool. I don't know if molecules have been made with other numbers of 'legs', such as milking stools, etc.

Thanks to Sean Pearce for suggesting this molecule.Megatomic Acid

This molecule has nothing to do with nuclear explosions, and neither is it the magic formula that creates a superhero. But it is in fact named after the black carpet beetle Attagenus megatoma (Fabricius), in which it is the principle component of the beetle's sex attractant. Its proper name is (3E,5Z)-3,5-tetradecadienoic acid.

Grass-Hopper Ketone

I'm guessing that this molecule gets its name as a result of laziness. It's extracted from the defensive secretions of the flightless grasshopper Romalea microptera, and I assume that after spending hours in the field, annoying the grasshoppers, and then catching them and 'milking them', the scientists involved were too tired to think of a proper IUPAC name, so they came up with the inspired name, grasshopper ketone.

Thanks to Polyploid2 for suggesting this molecule, and for more info see: J. Meinwald and L. Hendry, Tetrahedron Lett., 1657 (1969)

Shattuckite

This mineral sounds painful, but is actually just named after the locality in which it is found, the Shattuck mine in Arizona. Its actual formula is Cu5Si4O12(OH)2.

Thanks to Martin Harris for suggesting this mineral.

G(olf) proteins

These are a class of proteins called G-type proteins, some of which are linked to the olfactory system - hence the name G(olf) proteins. They help trigger the biochemical synthesis of neurotransmitters, which eventually leads to signalling, and gives us a sense of smell.

Germylene

The GeH2 radical is called germylene, which is similar to an antiseptic ointment found in the UK called Germolene. I doubt that germolene contains germylene, though, as GeH2 is very toxic...

Thanks to Victor Sussman for suggesting this molecule.

Khanneshite

It's amazing how this name got past the International Mineralogical Association when they approved the new mineral name. It was named after the discovery locality at Khanneshin, Afghanistan. All minerals have the suffix '-ite'. and so the name they gave to this mineral is - Khanneshite. I can only presume that there were no Scots on the committee that approved the name... I can't find any photos or structural images of khanneshite, so the image on the right is actually of the burbankite structure which, according to the literature is identical to that of khanneshite.

Thanks to Brian Jackson from the National Museums of Scotland for suggesting this mineral.

BCNU

Bis(Chloroethyl) NitrosoUrea has got quite an appropriate acronym, BCNU (be seein' you...), since in early medical studies it was found to be so toxic, it killed the patient! It is actually highly carcinogenic, causing tumors in rats, mice, rabbits, and probably humans as well. Ironically, it is actually used as a treatment for brain cancer and other diseases such as Hodgkin's lymphoma.

Thanks to Terence Bartlett for suggesting this molecule.SEX

SEX is the official abbreviation of sodium ethyl xanthate, which is a flotation agent used in the mining industry. Apparently you can get SEX in both solid and liquid forms (should that be hard and wet SEX?), and according to Australia's National Industrial Chemicals Notification and Assessment Scheme signs of high exposure to SEX include 'dizziness, tremors, difficulty breathing, blurred vision, headaches, vomiting and death'. Sound familiar...?On a related note, there's another flotation reagent, KAX, potassium amyl xanthate, which has the same function, and the same smell!

Austin

Austin has nothing to do with Austin cars, Austin Texas, or even Austin Powers...it's actually a mycotoxin, which comes from the fungus Aspergillus ustus, which might have given it it's name but I'm not sure.

Thanks to Chris Fellows for suggesting this molecule and to Mark Johnston for suggesting how it got its name.

Pantolactone

This molecule sounds like it belongs in underwear, or on stage in a pantomime. As you might expect, it is used as a reagent in the synthesis of CAMP ligands (cis-2-(aminomethyl)-1-carboxycyclopropane)...

Thanks to Gary Randall for suggesting this molecule.Technetium Cow

'Cow' terminology comes from the nuclear industry, and it has nothing to do with the unfortunate cattle that live near nuclear power plants. A radionuclide, such as 99Mo (as its ammonium salt), is stored in a column, called a 'cow'. Its decay product, technetium-99m, is continually produced, and it can be flushed out of the "cow column" in a process called 'milking the cow'. The 'technetium cow' isotope is then used in bone scans, and has a 6 hour half-life. On a related theme, molybdic acid anhydride (MoO3) is often referred to as 'Moo'.

Thanks to 'Plutonium' Page Sebring for providing the info about this element, and to Jonathan Montgomery for info on Moo.

Erectone

No, this isn't one of the ingredients in Viagra...but is actually one of a group of compounds extracted from the Japanese/Chinese herb Hypericum erectum, which is often used in traditional Chinese medicine to treat arthritis, rheumatism, and as an astringent.

Thanks to Christopher C. Wells for providing the info about this molecule.

Abiguene

Ambiguenes are cytotoxic and fungicidal indole alkaloids that are extracted from blue-green algae. As many as 7 are known. Although it could just be 5. Or 10. Or maybe they are a different type of molecule altogether...?

Thanks to Christopher C. Wells for providing the info about this molecule.

Lovenone

This is a cytotoxic agent isolated from the skin of a nudibranch (of course) Adalaria loveni which lives in the North Sea.

Thanks to Christopher C. Wells for providing the info about this molecule.

Boldine

This is an aporphine alkaloid extracted from the plant Peumus boldus. It is a good antioxidant and can protect the liver, although there are rumours it makes your hair fall out...

Thanks to Christopher C. Wells for providing the info about this molecule.Inflatene

This is a hydrocarbon compound that is isolated from soft coral (Clavularia inflata) and is apparently toxic to fish - maybe it makes them all look like puffer fish ;-).

Thanks to Christopher C. Wells for providing the info about this molecule.

Bowtiediene

This is another molecule named after its shape - although the preferred name is spiropentadiene.

Thanks to Isaiah Shavitt for providing the info about this molecule.

Prodigiozan

This molecule has a name that sounds like the Biblical 'prodigal son', who finally returned home. The structure shown is actually the related molecule, prodigiosin, since I can't find the structure of Prodigozan...well, not until it finally comes back here. :-) Both molecules are antibiotic pigments produced by Chromobacterium prodigiosum, with antimicrobial and cytotoxic properties.

Thanks to Susanne Wikman from Vaxjo University, Sweden, for providing the info about this molecule.

Arachidonic Acid

This molecule sounds like it has something to do with spiders, but it's actually made in the human body. It is synthesised from linoleic acid and plays an important stage in the inflammatory process of the human body - some Non-Steroidal Anti-Inflammatory Drugs (NSAID's) are believed to work by inhibiting this stage. But nobody has managed yet to artificially produce medical grade arachadonic acid (it's mainly used in infants) so the only source is rats urine - it needs a day's worth of urine from 10,000 rats to produce a single dose! Now, that really is taking the p***!

Thanks to Mark Croker for providing the info about this molecule.Warfarin

This molecule sounds like it could be a warfare agent, and it is...if you're a rat. It's a rat poison which stops the blood clotting, so the rats bleed to death. It also has medical uses in blood thinning and clot prevention. Apparently it gets its name since WARFarin was the first patentable product of the Wisconsin Alumni Research Foundation (WARF). An interesting story about warfarin is that it may have been used to kill Stalin.

Thanks to Charles Turner and Michael Bailey and Larry Baum for providing the info about this molecule.

(R)-DICHED

This is the abbreviation for (R,R)-1,2-dicyclohexyl-1,2-ethanediol. The authors of the paper which describes it (Organometallics, 2001, 20, 2920) state "a number of DICHED boronic esters were screened by NMR...". I wonder who the real DIC-HED is?

Thanks to Alex Yuen of the University of Sydney for providing the info about this molecule.

Lunatoic Acid

Lunatoic acid is an azaphilone isolated from Cochliobolus lunatus. It is a good antibiotic and also causes sporation in fungi. Perhaps it kills bacteria by causing them to die by insanity, in the same way canine distemper kills animals.

Thanks to Christopher Wells of the University of Sydney for providing the info about this molecule.

Microlite

Microlite is not one of the components of a small airplane, but is a tantalum/niobium oxide mineral that can be slightly radioactive. Its correct formula is: (Ca, Na)2Ta2O6(O, OH, F).

Thanks to Neil Brew for suggesting this mineral. More info can be found here.

beta-BuTX

This molecule sounds like the sales pitch for an exercise regime (get better buttocks using this!), but it's actually a snake venom with full name beta-Bungarotoxin). maybe the venom is more potent if the snake bites you on the Butx. :-)

Thanks to Satan's Little Helper and Joerg Fruechtel for info on this molecule.

DAMN

DAMN is the acronym for diaminomaleonitrile, which is a particularly nasty molecule containing lots of cyanide groups.

Thanks to Michael Stewart for suggesting this molecule.Allene

Allene is quite a sad molecule in Holland, since in Dutch it is called 'alleen', which simply means 'alone'. And if you add a benzene-ring you'll get Benzo-allene which means "I'm so lonely" in Dutch. Ahhhh....

Thanks to Karel Vervaeke and Harmen Lelivelt for info on this molecule.Proton Sponge

This molecule is 1,8-bis(dimethylamino)naphtalene, and according to the Aldrich Chemical Catalog, it is a very strong base with weak nucleophilic character due to steric effects. Therefore it goes by the

nickname 'proton sponge', since it mops up all available protons.

Thanks to Fernando Perna for info on this molecule.Mirasorvone

This molecule is part of the defensive chemistry of Thermonectus marmoratus, a beetle recently named the "sunburst diving beetle". The discoverers' at Cornell University named it in honour of the actress Mira Sorvino (right), who, as Dr Susan Tyler in the motion picture Mimic, successfully confronted the ultimate insect challenge.

Thanks to Andy Cal for info on this molecule, and more info is available at: http://www.pnas.org/cgi/content/full/95/6/2733.

Stichtite

Stichtite is a lilac coloured mineral which is a hydrated magnesium chromium carbonate hydroxide. This is fairly common as streaks and small lenses in the green Serpentine in the metamorphic rocks of Western Tasmania, but is very rare elsewhere. It was named after Robert Sticht, a director of a mining company.

Thanks to Martin Harris for info on this mineral.Cumene

Luckily, this molecule is actually pronounde 'coo-mene', so as to avoid sticky problems when ordering it. It's a fairly standard organic solvent, with a distinctive odour, that is used to make resins, polycarbonate, synthetic fibers such as nylon, and other plastics. Although pronounced the same, it has nothing to do with the Indian curry spice, cumin.

Thanks to J.J. Keating for info on this molecule.Flea

This is the commonly used name for the amphetamine, N-hydroxy-N-methyl-3,4-methylenedioxymethamphetamine (the N-hydroxylated version of MDMA, Ecstasy). The origin of its name is a bit strange, and is related to the fact that a commonly used code name for the parent compound, MDMA was ADAM. The 6-Methyl homologue was then called MADAM, and, following this pattern, the 6-Fluoroanalogue was to be FLADAM. So, with the N-Hydroxy analogue, the obvious choice was HADAM. But this brought to mind the classic description of Adam's earliest complaint, an infestation of fleas. The poem was short and direct: "Adam had 'em." So, in place of HAD 'EM, the term FLEA jumped into being.

See: http://www.erowid.org/library/books_online/pihkal/pihkal081.shtml for a full description of this naming process. Thanks to J.J. Keating for info on this molecule.

Wheelbarrow Molecule

Here's a molecule that has been designed to look like a wheelbarrow. It doesn't seem to have a full name yet, so it's just called Wheelbarrow Molecule. What's next, a molecular lawn mower? Pruning shears?

Thanks to Plutonium Page for info on this molecule, and the full paper can be seen at: Tet. Lett. 44 (2003) 6261.

Syringic Acid

This molecule is named after the lilac plant, since the Latin name of lilac genus is Syringa. Lilac bushes possess hollow sticks which were used in ancient times to make flutes. In fact, there is a kind of flute that is called "siringa" in Spanish. In Latin the meaning of the word siringa was extended to include hollow tubes made of any material, including metal. Later, when hollow needles began to be used to inject liquids in the body, quite naturally they were called syringes. Funnily enough, syringic acid can be found in blueberry plants, which, in Latin, are called Vaccinium. Quite a coincidence! On a related theme, there is also a Vaccenic acid (Z-11-octadecenoic acid, also known as asclepic acid) although its structure is not related to that of Syringic Acid.

Thanks to Andrei V. Rogoza, Kastytis Beitas, Gabriel Tojo and to ShadowFox for info on this molecule, and to Tue Bruun Petersen for the info about vaccenic acid./p>

Tortuosine

This molecule is an alkaloid extracted from the plant Amaryllidaceae, but I bet it was extracted very sloooowwwllly. In fact, this naturally occurring organic compound and the following one (assoanine) had plant-derived names that were so compelling that Lee Flippin designed and executed total syntheses of them just for the fun of it.

Thanks to Lee Flippin for info on this molecule. More details: J. Org. Chem., 65 (2000) 3227.

Assoanine

This molecule gets its superb asinine name from the plant from which it is extracted, the gloriously named Narcissus assoanus!

Thanks to Lee Flippin for info on this molecule. More details: J. Org. Chem., 59 (1994) 3497.

Bicyclohexyl

This molecule not only has a name that sounds like a bicycle, ironically it even looks like one too. In fact, the bicyclohexyl compound with isopropyl and methyl sidechains (2-isopropyl-3'-methylbicyclohexyl, shown in the diagram) looks even more like a bicycle. There is also tricyclene, but unfortunately its structure looks nothing like a tricycle.

Thanks to Joris van den Heuvel for suggesting this molecule and to Geoff Hallas for correcting the structure.

NanoPutian Molecules

And today's award for the 'How did they possibly get a grant to do that?' paper, goes to the J. Org. Chem . article by Chanteau and Tour from Rice University in Texas. It concerns making anthropomorphic molecules - i.e. molecules that look like humans...but why anyone would want to do this I don't know... They have been named NanoPutians, after the little men from Lilliput in the book 'Gulliver's Travels'. They come in many forms - the basic building block is the NanoKid (shown right), and from this other variants can be made, such as NanoAthlete and NanoBaker.

Thanks to Neil Edwards for suggesting these molecules.

Nanocars and Nanotrikes

These are the perfect vehicles for driving Nanoputians around their nanoworld. They are made from a rigid framework of benzenes and acetylene groups, with either three or four C60 molecules attached at the ends as 'wheels'. I always wanted a compact...

Thanks to Andrew Byro for suggesting these molecules.See: Y. Shirai et al, Nano Letts. 5(11), (2005) 2330.

Anisole

Anisole sounds like a molecule the devil would be very interested in collecting, or maybe it's James Brown's ('The Godfather of Soul') favourite molecule? Anisole is aromatic in both the chemical and olfactory sense, and is used in perfumery. It is also an insect pheromone. If you have a lisp, please don't confuse anisole with anethole, which is a structurally related natural product which, incidentally, has the flavour of aniseed.

Dopamine

Dopamine (pronounced DOPE-a-mean) is a neurotransmitter in the brain. It is connected to pleasurable sensations (feeling doped) and has been shown to be connected to drug abuse and addiction. Maybe that's why Dopey always had that silly grin on his face...

Thanks to Andrew Byro for suggesting this molecule.BIG CHAP

This wonderfully named molecule has nothing to do with reproductive hormones, but is actually a detergent with proper name N,N-bis(3-D-gluconamidopropyl)cholamide. Apparently the molecule has reduced electrostatic interactions that prevent your BIG CHAP getting stuck in a chromatography column...

Thanks to Stephen FTM Thompson for suggesting this molecule.

ASS

This is the commonly used acronym for argininosuccinate synthetase, which is a chemical found in the brain. So it seems some people really do think with their ASSes...

Thanks to Allart Kok for suggesting this molecule.

Horseradish Peroxidase

This is the version of the peroxidase enzyme that is isolated from the horseradish plant. Like all peroxidases, it converts harmful peroxide molecules (H2O2) into water molecules (H2O). It is also used to label proteins and nucleic acids as an alternative to radio labelling. The molecule to be labelled is attached to the horseradish peroxidase molecule, and the mixture is then exposed to a substrate that changes from clear to coloured when it is oxidized by HRP. When some of the variations of this enzyme are used as a labels for antibodies, they go by names such as anti-mouse, anti-rabbit, and

worryingly...anti-human.

Thanks to Andrew Patterson for suggesting this molecule.Kojik Acid

This sounds like Telly Savalas' favourite molecule. He was the star of the US TV cop show from the 1970s called 'Kojak'. Kojic acid is used as a skin whitener...but does it work especially well on bald heads?

Thanks to Jerry Van Cleeff for suggesting this molecule.Porkane

I'm pretty certain this is a spoof molecule, since one of the carbons has 5 bonds. These pig-shaped molecules, where the 'tail' can point up or down, are apparently isolated from porcine lard (pig fat). There are various derivatives of this, including norporkanone, epiporkanone and neoporkanone. For more info on the porkanes, see here.

Thanks to Victor Nikolaev for suggesting this molecule.Spiroagnosterol (Vice Presidential Steroid)

Years ago this molecule was called the "Vice Presidential Steroid" because of the similarity in name to Spiro Agnew. Mr Agnew was, of course, the Vice President of the U.S. from January 1969 until October 1973, when he resigned. (I've never found a proper reference to this molecule in the literature - does anyone have it?)

Thanks to John L. Meisenheimer, Sr for suggesting this molecule.

Nagarse

Nagarse is a broad-specificity protease, also known as Bacillus amyloliquefaciens subtilisin. It seems to be used to break apart proteins and DNA strands for analysis purposes. Its source is a bacterium and a leech (hirudo medicinalis).

Thanks to Richard Cammack for suggesting this molecule.Hardwickiic acid

This is a diterpene which got its name since it was first isolated from the Indian tree Hardwickia pinnata. I assume the tree was named after someone called Hardwick. Anyone know?

Thanks to J.J. Keating from University College Cork for suggesting this molecule and to ShadowFox for more info about it. Ref: R. Misra, R.C. Pandey, S. Dev, Tetrahedron 35 (1979) 2301.

Aristolochic acid A

This aristocratic sounding molecule is derived from species of the birthwort plant (aristolochia). Plants containing the compound were used in herbal medicine as anti-inflammatory agents, but they are now banned in the US and Europe as the compound is nephrotoxic (toxic to the kidney).

Thanks to J.J. Keating from University College Cork for suggesting this molecule. Ref: Fundamentals of Pharmacognosy and Phytotherapy by M. Heinrich, J. Barnes, S. Gibbons and E. Williamson (Churchill Livingstone, 2004., pg 165)

CAMP

This is actually short for cyclic adenosine monophosphate (cAMP) and is a signalling molecule which can be found in almost all eukaryotic organisms. For example, it is used as a nutrient sensor in yeast, and is one of the building blocks of DNA. I wonder if it's responsible for the so-called 'gay gene'...

Thanks to Han Lim for suggesting this molecule and to Tom for info about it.

Cucurbituril

This molecule, which is shaped like a Halloween Jack'o'Lantern, is named after the Latin word for pumpkin (Curcubita pepo). It is now finding lots of use in medical drugs or in potential molecular electronic devices due to the fact that other long thin molecules can be threaded through the hole in the centre to make so-called 'rotaxanes'.

Hipposudoric Acid

This is a malodorous blood-red pigment found in hippo sweat. It absorbs ultraviolet light, thus blocking out the sun's rays like a sunscreen. It is also a natural antiseptic. Its red colour is responsible for the myth that hippos sweat blood.And still on the hippo theme, there's a molecule called Hipposulphate A, which is a poisonous sulfated sesterterpenoid that's found in a sponge, Hippospongia metachromans, living near Okinawa.

Thanks to Charles Turner for suggesting Hipposudoric Acid, and to Christopher Wells for Hipposulphate A.

Old Yellow Enzyme

This is a flavoprotein that reversibly oxidises NADPH to NADP and a reduced acceptor. In fact, yellow enzymes are any of a number of enzymes having a flavin as a prosthetic group. Historically, NADPH dehydrogenase (occurring in plants and yeast) was called the Old Yellow Enzyme to distinguish it from D-amino acid oxidase, known as, of course, the New Yellow Enzyme.

Thanks to John Moody for suggesting this enzyme.Ladderane

Ladderane is a chain of fused cyclobutane rings that make up the bulk of dense membranes in certain unusual bacteria. They were discovered in anammox bacteria, which anaerobically oxidize ammonia to dinitrogen. The staircaselike structure of cis-fused cyclobutanes has never before been seen in nature. The most abundant lipid in the bacteria is the methyl ester of a C20 fatty acid with five fused rings. Other ladderane lipids contain three fused cyclobutane rings attached to a cyclohexane.

Thanks to Erik Holtzapple for suggesting this molecule.

Snottites

These are gelatinous, dripping microbial draperies ("mucus stalactites") composed of elemental sulphur, iron oxide crusts, gypsum, and densely packed bacteria, and are found in caves. They are formally known as biovermiculations, although snottite is more descriptive. Snottites are produced by sulfurphilic micro-organisms and drip sulfuric acid with a pH of 0.3 to 0.7. Other microbial structures include "blue goo," which are lavender structures attached to the walls of the cave, and "red goo," a complex clay breakdown product containing clusters of bacterial cells and having a pH ranging from 3.9 to 2.5. Other microbial stalactites go by the fancifully names of "phlegm balls," "green slime," "punk rocks," "hairy sausages," "slime balls," and "beads on a string."On a similar theme we also have: Coprolites, which are fossil feces, Regurgitalites, which are fossil vomit or pellets, and Cololites, fossilised stomach, gut, or colon contents.

Coalingite

This superbly named mineral takes some licking... It is actually an interstratified hydroxyl carbonate, but whenever anyone says its name, they normally lower their voices for the rest of the discussion, probably because it sounds like a contraction of coitus and lingus. But it was fact a mineral named after being found in the vicinity of the town of Coalinga, California, which was itself named after 'Coaling Station A'.

Thanks to Phillip W Barak of the Virtual Museum of Minerals and Molecules for suggesting this mineral.

Nootkatone

This molecule with a very silly name is used as a food additive to give grapefruit flavours, as well as in the perfume industry to give odours of citrus fruits and orange peel. It got its name from the yellow cedar, or Camaecyparis nootkatensis, which was itlself named after the native North American called the Nootka.

Thanks to Jim Gobert for suggesting nootkatone and to ShadowFox for some info about its name. Click here for more info on the structure of nootkatin.

Bongkrekic acid

Any visitor to an Indonesian market or dinner table will almost certainly come across tempe (below left), though wonder what on earth it really is. Closely resembling a Camembert cheese in colour and texture with a mushroom-like aroma, tempe is in fact one of the world's first soybean foods. It is composed of cooked soybeans that have been fermented through by an edible fungus which, when mature (like a cheese) becomes an attractive and aromatic white cake suitable for a variety of uses in hundreds of local dishes.

But deep in the mountain villages in Central Java, there used to be one rare deadly variety of tempe. Very rare nowadays, and never sold openly anymore, this tempe has killed hundreds. So dangerous is this tempe that the

government has banned manufacture of it and imposed a prison sentences to anybody caught making or selling it, since this tempe can contain a toxin more deadly than cyanide. This is tempe Bongkrek. Made from coconut residue after the oil has been extracted, and nothing like good safe soybean tempe, this tempe has the problem that it may become contaminated with a deadly bacterium that lives on the fermented coconut, called Pseudomonas. The coconut only grows the bacterium if it is heavily contaminated, and may produce a deadly respiratory toxin called Bongkrekic acid (above right). In 1988 one batch killed 40 people within two days and over a hundred others were hospitalised. The community in this area, well aware of the risks, have nevertheless continued to eat Bongkrek despite a ban by the government, so irresistible is the taste and texture of this dangerous and illicit pleasure.

Thanks to Tim Lyon for suggesting this molecule.

Bullvalene

This is a very unusual molecule, in that it is fluxional...all the carbons are equivalent due to the rapid movement of the double bonds around the structure. It was first predicted to be like this over 20 years ago by Professor 'Bull' Doering, and was only synthesised in the lab many years later, whereupon his controversial predictions about the structure were verified. The name is thought to be derived from his nickname, 'Bull', but other reports suggest that it was given its name by an irreverent and skeptical graduate student that thought such a structure couldn't exist, and so called it 'Bull-valene'.

Thanks to Marc Kaminski for suggesting this molecule. See: J. Chem. Edu. 78 (2001) 924, for more info.

Barrelene

This molecule is closely related to bullvalene, and got its name from its similarity to the shape and structure of a barrel. Peter Lykos emailed me to say how it happened: "When Howie Zimmerman was getting started at Northwestern University I heard he had synthesized a molecule that in effect was three ethylene molecules condensed about two

methyl axes. I could not give it the correct organic chemist's systematic name (I am a quantum chemist) but was fascinated by the notion that there might be a delocalization of six π-electrons around the molecule. So when I called him about its spectroscopic properties I referred to it as 'barrelene' following the idea that the lateral delocalization mught be like the staves of a barrel. He apparently liked that name so that became its trivial standard name".

SnOT

Tritiated tin hydroxide goes by the wonderful chemical formula of SnOT. David Ball, a chemist in Cleveland Ohio, was working on isotopomers of SnOH, and after tritiating it found he got SnOT. His paper concludes with the wonderful phrase "Since Wang et al did not use tritium substitution, we can state with certainty that there was no SnOT in their samples".

Thanks to David Ball for studying SnOT and suggesting it for this page. See: D.W. Ball, J. Mol. Struc. (Theochem) 626 (2003) 217, for more info. Thanks also to Sky for the use of the photo of him playing a beggar in a re-enactment of the English Civil War for the Sealed Knot Society.

DOPE

Apparently, DOPE is commonly used by membrane chemists and biochemists - which is something I've always suspected... It's actually short for 1,2-Dioleoyl-sn-Glycero-3-Phosphoethanolamine, and it's a phospholipid used for research into membrane structures. A variant on this is called DOGS, so if you take DOPE, you may

go to the DOGS...Flufenamic Acid

This molecule with a very fluffy name has anti-inflammatory and antipyretic properties, and is used to treat inflammatory rheumatoid diseases and relieve acute pain. Its chemical name is N-(3-trifluoromethylphenyl)anthranilic acid, which doesn't sound quite as friendly and fluffy as its common name. In other languages it is called Flufenaminsäure (German), flufenaminezuur (Dutch), ácido flufenamico! (Spanish), and acide flufenamique (French).SNOG

SNOG is a utility carrier of nitric oxide which breaks down to produce nitric oxide and a glutathione radical at pH 7.4. Its proper chemical name is S–Nitrosoglutathione. Unsurprisingly, one effect of SNOG is that it apparently causes smooth muscle relaxation... For those of you unfamiliar with UK slang, a 'snog' is a deep passionate kiss, similar to the one Britney is giving Madonna in the photo on the right...

Hirsutene

This is an important biological molecule, although what its function is, I'm not sure. Perhaps it makes things hairy...?

Indenyl

This sounds like it could be a pollutant found in some Egyptian rivers (i.e. in de Nile...), but it's actually a fusion of a cyclopentadienyl ring with a benzene ring, and is often used as a ligand for metallocene synthesis.

Forskolin

Despite the odd name, forskolin is not what they remove from the baby during ritual circumcision. In India, practitioners of traditional Ayurvedic medicine have long used the herb Coleus forskohlii to treat asthma, heart disease, and a range of other ailments. In the 1970s, researchers isolated a chemically active ingredient in the herb and called it forskolin. Now available in supplement form, this extract is commonly recommended for treating hypothyroidism, a condition in which the thyroid gland produces too little thyroid hormone. Forskolin is believed to stimulate the release of thyroid hormone, thus relieving symptoms as fatigue, depression, weight gain, and... dry skin.

Wrenchnolol

This is a molecule that looks like a wrench, and is an anti-cancer drug. The "jaw" part of the compound mimics the helical interface of the activation domain of a transcription factor molecule, and the "handle" region accepts chemical modifications for a range of analysis.

Thanks to Mackay Steffensen for suggesting this molecule. More details: J. Am. Chem. Soc. 126 (2004) 3461.

Sex Muscle Abnormal Protein 5

The European Bioinformatics Institute houses the Macromolecular Structural Database, and for quite a few years the most downloaded structure from that site was PDB code 2SEM: it contained a protein called "Sex muscle abnormal protein 5". Obviously, search engines had indexed all the PDB files, and you can guess what kind of searches had returned this structure! The protein comes from Caenorhabditis Elegans, which is a tiny worm (about 1 mm long) and was the first true animal to have its genome completely sequenced. The people who reported this protein were investigating its crucial role in the development of the worm's vulva (Clark et al, Nature, 1992 Mar 26, 356(6367):285-6). As the amount of dubious material available on the internet has grown, interest in this protein from persons 'outside the scientific community' has declined. On a similar theme, there's another molecule called SexA I, which is a restriction enzyme from Streptomyces exfoliatus that cleaves the DNA sequence A/CCWGGT.

Thanks to Peter Keller of the Macromolecular Structural Database, European Bioinformatics Institute, and Lily Zhou from the University of Michigan, for suggesting these molecules and telling me their details.

Sillimanite

This mineral wasn't named after the clumsy fool that tripped over it, but was named in honour of the American mineralogist Benjamin Silliman (1779-1864), who was a chemistry professor at Yale. It is a form of aluminium silicate, with no real value, except in Idaho, where the Clearwater River Valley has sillimanite cobbles that are carved into figurines and sold as souvenirs of Idaho.

Thanks to Hope Nesmith for suggesting this mineral.Thebacon

This molecule certainly brings home the-bacon. It has a similar structure to diamorphine (heroin) but has only one acetyl group instead of two, and the other group is replaced with a CH3O- group. Apparently, thebacon hydrochloride is a centrally acting cough suppressant sometimes used to treat coughs. This molecule isn't to be confused with BaCoN (barium cobalt nitride), which is a black crystalline solid with a layered structure (strips of BaCoN?)

Cryogenine

Cryogenine A (also known as Vertine) is the active constituent of Sinicuichi plant. It apparently can give audio hallucinations, but I don't know why it is called cryogenine...maybe because after you stop using it you go through very, very cold turkey? In fact there are two totally unrelated, and different molecules called cryogenine. The other one, Cryogenine B, is usually called phenylsemicarbazide, and has been found to be carcinogenic in mice.

Lagerine and Bebeerine

I wonder if lagerine is sold by the pint? It actually has nothing to do with beer, it gets its name from being a constituent of the crape myrtle (Lagerstroemia indica L.) plant. Bebeerine too, has nothing to do with beer. It's an alkaloid molecule derived from the Caribbean bebeeru tree, and helps to protect it from beetles.

Jawsamycin, Histrionicotoxin and Yessotoxin

Highly toxic, and are normally isolated from biological sources. Jawsamycin was discovered in 1989 by Fujisawa, a Japanese pharaceutical company, it has only recently been synthesised. The metabalite is composed of a chain of five carbon triangles (cyclopropyls), giving it its name because of the resemblance to shark's teeth. The compound, however, has 10 chiral centres, points about which mirror images of the molecule can form for a total of 1024 possible isomers, only one of which is jawsamycin.Histrionicotoxin is a poison found on the skin of a certain tree frog in South America (Dendrobates histrionicus), and is used by the native indians on their blow-pipe darts.Yessotoxin was first isolated from the digestive organs from scallops (Patinopecten yessoensis) in Japan and is believed to be produced by microalgae.

Sarcosine

This is one for all our French readers... Nicolas Sarkozy (right) is currently the President of France, and, as such, it's appropriate that he has a molecule with a similar name. Sarcosine is a sweetish crystalline amino acid found in muscles and other tissues, and is also called N-methylglycine.Another molecule which sounds odd in French (but not in English) is pyralene, which has been used in the past as an insulating oil in electric transformers. In French it is pronounced "pire haleine", which means "worst breath". This is ironic, since use of pyralene was abandoned after transformer fires were giving off toxic fumes.

Thanks to Thomas Jeanmaire for suggesting sarcosine, and Marc Schaefer for pyralene.

Enflurane

Yet another one for the French speakers... Enflure in French means a twit, a clot, or a jerk, or can also mean a swelling or inflamation. Enflurane is an outdated halogenated ether that was commonly used for inhalation anesthesia during the 1970's and 1980's. A curious (but apparently true) story about enflurane relates to its pre-human work. Enflurane and Isoflurane are isomers, and they were being investigated for their safety and efficacy as anaesthetics. Isoflurane is by far the better of the two, but was initially held back from clinical use because test experiments showed it gave cancer to rats. It turns out that the rats that were given enflurane were given different food to the ones using isofluran, and those exposed to isoflurane were being fed pellets which had become contaminated with a known carcinogen. By the time the toxicity experiments were repeated (and isoflurane found to be innocent in this regard), the poor relation, enflurane (which had passed all the previous tests with flying colours), had already been on the market for a few years. Had the contamination not occurred, it is doubtful that enflurane would ever have made it on to the market at all. Enflurane was never popular, and its manufacture has ceased because the makers could not sell enough of it to make its production economical. Isoflurane, meanwhile, led the way as the mainstay of inhalational anaesthesia in the Western world for several decades.

Thanks to Thomas Jeanmaire for suggesting this molecule, and to Ken Ruiz for the isoflurane story.

Shikimic Acid

Here's one for our German-speaking readers. Shikimic sounds very like the German word 'Schickimicki', which means a (snobbish) member of the in-crowd, a trend-setter, or a 'designer-label-wearing' sort of person, for example, Posh and Becks in the picture, left. Shikimic acid was first isolated from the Japanese flower shikimi, hence its name. It's used as a starting molecule in the synthesis of the anti-flu drug Tamiflu.

Thanks to Kutti for suggesting this molecule.Mandelic Acid

Mandelic Acid is not named after Nelson Mandela, the world famous South African polician and winner of the 1993 Nobel Peace Prize, although his youthful appearance might be due to it....as mandelic acid is often used in skin creams to smooth away wrinkles. It's also used as an antiseptic ingredient particularly against urinary tract infections.

Thanks to Antony Bigot for suggesting this molecule.Soddyite

This is a silicate mineral that was named after Frederick Soddy (1877-1956), the British physicist and radiochemist. In German it's known as Soddyit and it has the formula (UO2)2SiO4·2H2O.

Thanks to Sean Pearce for suggesting this mineral.Kutnahorite

This is a another mineral that geology students love to mispronounce as "cuttin' a whore right". It's a CaMn(CO3)2 mineral originally from Czechoslovakia, and described as a massive and granular material occurring in veins. Its color is almost always some shade of pink, with well-developed cleavage with cleavage surfaces that are commonly curved (aren't they always?).

Thanks to Dave Chapman and Jason Stouffer for suggesting this mineral.

Mucic Acid

Pronounced 'Music acid', this is quite different to Acid Music... This chemical is obtained by the nitric acid oxidation of milk sugar (lactose), dulcite, galactose, quercite and most varieties of gum. It is also called Galactaric Acid. The "mucic acid test" in basic biochemistry lab is a well-known test for D- or L-galactose. The test is carried out by oxidising the sample with concentrated nitric acid; mucic acid crystals will form after leaving the solution overnight. Isn't chemistry great? Just add some acid, and you get some music...

Thanks to Warut Roonguthai for suggesting this molecule.Burpalite

This mineral with the wonderful name of burpalite, Na2CaZrSi2O7F2, is named after the Burpala massif in Buryatia, Russia. It sounds a bit like a medicine you give to babies to make them burp...

Thanks to Willem Schipper for suggesting this mineral.Rhamnetin

This molecule with an amusingly double-entendre name (ram'n it in) actually gets its name from the Buckthorn berry (Rhamnus cathartica), of which it is a derivative. It is a yellow pigment used in the dye industry.

Thanks to Geoff Hallas for suggesting this molecule.DNA origami

This is a new development in which strands of various lengths of DNA can be 'stitched' together to make nanoshapes. The picture (left) shows AFM images of just some of these shapes (scalebar = 100 nm), including nanostars, and nanosmileys, but you can even write nanomessages using nanoletters and draw nanomaps of the world (see below).

One obvious application of patterned DNA origami would be the creation of a ‘nanobreadboard’, to which diverse components could be added. The attachment of proteins, for example, might allow novel biological experiments aimed at modelling complex protein assemblies and examining the effects of spatial organization, whereas molecular electronic or plasmonic circuits might be created by attaching nanowires, carbon nanotubes or gold nanoparticles.

See: P.W. Rothemund, Nature 440 (2006) 297.

Olympiadane

This molecule consists of five tiny interlocking rings, which mimics the Olympic Games symbol, and so is named 'Olympiadane'. It was first made in 1996, in commemoration of that year's Olympic Games. The successful linkage of these highly complex synthetic molecules means that molecular chains of any length could be constructed with many applications, particularly in the areas of information storage systems and the creation of a 'molecular computer'.

Thanks to Wendy Hunt for suggesting this molecule.MAP-kinase-kinase-kinase

Mitogen-activated protein (MAP) kinases are proteins that respond to extracellular stimuli (mitogens, e.g. a chemical or protein) and regulate various cellular activities, such as gene expression, mitosis, differentiation, and cell survival or death. As you might expect, a protein that acts upon a MAP-kinase, is called MAP-kinase-kinase. This can go up two more levels, until we have the wonderfully-named 'MAP-kinase-kinase-kinase' - a protein which acts on MAP-kinase-kinase, which acts on MAP-kinase, as a part of intracellular signalling. Now, if another protein were to act on that molecule, I wonder what they'd call it...hmmm

Thanks to Leigh S. Arino de la Rubia for suggesting this molecule.Coproverdine

This molecule is a new anti-tumor drug that was isolated by the University of Canterbury (Christchurch, New Zealand) from a sponge which was discovered off the coast of New Zealand. In the National Institute for Water and Atmospheric research (NIWA) archives, it is recorded as being "Green-sheep-sh*t like in appearance". The alkaloid they discovered was cytotoxic, but they needed a catchy name for it. They settled on "Coproverdine": Copro - sh*t, Ovis - sheep, and verdi - green.

Thanks to Martin Lee from the Department of Chemistry, University of Canterbury, NZ, for suggesting this molecule, and who apparently spent a year trying to make it!.

Labradorite

Labradorite is a silicate mineral that is named after Labrador in eastern Canada, where it was first discovered. Labradorite can produce a colourful play of light across cleavage planes and in sliced sections, called labradorescence, which sounds a bit like a perfume based on the smell of old dogs, or maybe the glow from a radioactive dog! The usually intense colours range from the typical blues and violets through greens, yellows and oranges. The colour display is from lamellar intergrowths inside the crystal.

Thanks to Chris Miller for suggesting this mineral.'Banana' Borane

This isn't an official name, but I'm told that many chemists who work in the organoborane field use the nickname 'banana borane' to describe molecules such as 9-borabicyclo[3,3,1]nonane, abbreviated BBN. This is because rather than draw out the proper structure (top), they simply draw the borane as a banana shape with the bridging B group sticking out.

Thanks to Rob Saunders for suggesting this fruity molecule.Skunky Thiol

This molecule is what makes beer taste bad after it's been left exposed to sunlight for a few

hours. The actual name is 3-methylbut-2-ene-1-thiol, or 3-MBT for short, but since it's related to molecules found in skunk spray, and it stinks, it's also known as skunky thiol. Only a few nanograms of this thiol in one litre of beer are enough to give the offensive flavour.

Thanks to Matthew Latto for suggesting this smelly molecule. More info: http://www.rsc.org/publishing/journals/PP/article.asp?doi=b609337j

Fartox

On a related theme, this molecule is actually called pentachloronitrobenzene, but goes by a variety of tradenames, including Quintozene, Earthcide and best of all, Fartox. It seems somehow appropriate that Fartox should be a pale yellow solid with a slightly musty odour. It has been used as a soil fungicide since the 1930's, but I have no idea how it came to have this silly name. Maybe it was due to a side-effect of eating fruit sprayed with it?

Dinocap

Dinocap sounds like a dinosaur's hat, or a hat that looks like a dinosaur. It's a dark red viscous liquid that's used to kill mites, fungus and mildew on crops, and goes by the trade name Karathane. There are 2 different versions of dinocap; dinocap-4 is the one shown on the left, and dinocap-6 has the positions of the two blue side-groups swapped. In either case, the liquid is actually a mixture of different isomers, with R1=CH3(CH2)n and R2=CH3(CH2)5-n. I'm pretty sure the 'dino-' part of the name comes from 'dinitro-', but the 'cap' remains a mystery.

Naftazone

This sounds like a pretty naff molecule. (For non-UK readers, 'naff' is English slang for poor quality, unfashionable or rubbish). It's used as a drug to protect blood vessels (a 'vasoprotector') - so, maybe it's not quite so naff after all. Its name comes from a contraction of its full name (1,2-naphthoquinone-2-semicarbazone) and has nothing whatsoever to do with the North American Free Trade Agreement (NAFTA).

NUN

This molecule could be habit-forming...It's actually a linear molecule of uranium nitride N-U-N, made by inserting uranium atoms into molecular N2.

Thanks to Ian for suggesting this pious molecule. More info: R.D. Hunt, J.T. Yustein and L. Andrews, J. Chem. Phys., 98, (1993) 6070.

Discodermolide

Could this be John Travolta's favourite molecule? It's a recently discovered polyketide natural product found to be a potent inhibitor of tumor cell growth, and it gets its name since it was first isolated in 1990 from the Caribbean marine sponge Discodermia dissoluta. Since the compound is light-sensitive, the sponge must be harvested at a minimum depth of 33 metres - so, no disco lighting there then...

More info: Wikipedia.

Jimthompsonite

This is actually a mineral - a mixture of iron and magnesium silicates, with formula (Mg;Fe2+)5Si6O16(OH)2 - that's found in a talc quarry, near Chester, Vermont, USA. It was named after Professor James Burleigh Thompson, Jr., who was an eminent petrologist of Harvard University in the 1940s and 1950s. This is a different Jim Thompson to the one who helped establish the silk industry in Thailand. There's a slightly different version (monoclinic crystal) of this mineral called clinojimthompsonite.

Thanks to David French for suggesting this mineral.

Pregnane

This is a steroid molecule that is the parent compound for many hormones, including the pregnancy hormone progesterone.

Thanks to Vincent Schüler for suggesting this molecule.

Asparagine

I wonder if this molecule tastes of asparagus? In fact it gets its name since it was first isolated in 1806 from asparagus juice, and was the first amino acid to be isolated. It is one of the 20 most common natural amino acids on Earth and can be synthesised in the body. Interestingly, the smell observed in the urine of some individuals after consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. However, some scientists disagree and implicate other substances in the smell, especially methanethiol.

Thanks to Vincent Schüler for suggesting this molecule.Analcite

I thought it was time to show you my analcite! Actually it's a mineral, and although analcite is a valid name for it, it normally goes by the less amusing name of analcime. It's a form of sodium aluminium silicate, and it gets its name from the Greek word meaning 'weak', referring to a weak electrical charge developed on rubbing. So if you rub your analcite, you may get a shock...

Thanks to Daniel Manke of Central Michigan University for suggesting this mineral.Gingerol

Gingerol isn't the molecule responsible for ginger hair and freckles. Instead, it's the active constituent of fresh ginger. Gingerol is a relative of capsaicin, the compound that gives chilli peppers their spiciness. It's normally found as a pungent yellow oil, but also can form a low-melting crystalline solid. Cooking ginger transforms gingerol into the compound with a 'zing', zingerone.

Thanks to Neil Anderson from Denmark for suggesting this molecule.

Porphyrin Hamburger

A team of researchers at Osaka University, Japan, fused a molybdenum-porphyrin complex and a tungsten polyoxometalate to form a compound they have named the 'porphyrin hamburger'. Two saddle-shaped porphyrin complexes make up the burger buns, while a cluster of tungsten oxide anions surrounding a central silicon cation, known as a polyoxometalate, forms the meat sandwiched between them. The molecules are joined by stable coordination bonds.

This must give plenty of opportunity for derivatives along the lines of Porphyrin Cheeseburger. Or perhaps you could even attach penguinone to make a penguin burger? Or even attach a molecule of cocaine to get a burger and coke?

The porphyrin hamburger: W atoms are shown in pink, O in red, Mo in green, C in grey

and N in blue. The central Si ion is shown in dark grey.

Folk Acid

This is nothing to do with folk music, or even acid folk, it is simply a mis-spelling of folic acid, which itself gets its name from the Latin word folium meaning 'leaf'. This seems to be a particlarly common mis-spelling, and occurs even in scientific papers and textbooks (try it on google), maybe a result of word-processing programs automatically 'correcting' words they don't recognise, or just that scientists can't spell.

PORN

Now that we have the word 'PORN' on this site, it'll either get banned or increase the hit rates hugely! Unfortunately, this PORN is simply the acronym for poly-L-ornithine, a molecule used in cell culture experiments. I suppose that to form a polymer it does involve lots of frantic couplings...so PORN maybe isn't such an inappropriate name after all.

Thanks to Debbie Radtke for suggesting this molecule.CuNT

This one must be mother of all silly acronyms! Carbon nanotubes are often abbreviated to CNTs, and single-walled ones to SWCNTs. But when a Chinese group recently fabricated copper nanotubes, unbelievably they decided to call them CuNTs! In the same paper they describe bismuth nanotubes, and called them BiNTs. Either they named these 2 structures for a bet - just to see if the Royal Society of Chemistry would publish a paper containing numerous (over 50!) references to BiNTs and CuNTs, or they just didn't realise the meanings of these two acronyms. Or maybe they just did it to increase the number of hits they receive from online searches...

Thanks to Keith Bromley for spotting this paper, which is: D. Yang, G. Meng, S. Zhang, Y. Hao, X. An, Q. Wei, M. Yea and L. Zhang, Chem. Commun., (2007), 1733.

Scorpionate ligands

The scorpionate ligand gets its name from the fact that the ligand can bind a metal with two donor sites like the pincers of a scorpion. The third donor site reaches over the plane formed by the metal and the other two donor atoms to bind to the metal, like a scorpion grabbing the metal with two pincers before stinging it. The most popular class of scorpionates are the tris(pyrazolyl)hydroborates or Tp ligands, and this is shown bonding to a Mn(CO)3 group, below. Another scorpion-like molecule is bis([1,2]dithiolo)-[1,4]thiazine, which is sometimes unofficially called sscorpionine.

Puberulin

This wonderfully named molecule gets its name from the fact that it's isolated from the African shrub A. puberula. Hmm, I wonder what you'd measure with a pube-rula...

Bender's salt

Is this what gay chemists put on their fries? (In the UK, a 'Bender' is a derogatory slang name for a male homosexual). Or maybe it's the salt that Bender from Futurama would use. It's potassium ethylthiocarbonate (C3H5KO2S) and is named after the German Chemist Friedrich Bender.

For more details see: R. Fischer, G. Fessler, Pharmazie. 10 (1955) 349.Biline

A reporter's favourite molecule? (They always want their by-line). This is a bile pigment, and there are various versions depending upon which nitrogen the H goes (in the diagram it's on N-21, so the molecule shown is 21H-biline), and what side chains (if any) there are.

Blasticidin

And here's one for the military, or maybe just a gung ho chemist (Blast its side in!). It's actually an antibiotic fungicide, and is also used in genetic engineering experiments to fuse pieces of DNA together to make resistant genes.

For more details see: http://www.blasticidin.com.

Noselite

A superb mineral name, that sounds like just the sort of thing a geologist needs to find his way around ina dark cave. It's a silicate mineral with formula Na8[SO4|Al6Si6O24], and named after the German mineralogist Karl Wilhelm Nose, and also goes by the name of nosean - as in "I've just been nosean around this rock face". For experiments involving real nose-lights, where the researcher stuck lightbulbs up the noses of volunteers to see how it affected their visual performance, see the wonderfully bonkers paper by N.E. Wetherick (Nature 266 (1977) 442.)

For more details see: http://www.webmineral.com. Thanks to Peter Rice for the Nature reference.

Brick Acid

'Brick acid' is the nickname given to good old hydrochloric acid (a.k.a. muriatic acid), since it's commonly used by builders to clean up the mortar smudges in brickworks and paving. Some manufacturers sell 'brick acid' as a mixture of 10-30% aqueous HCl with added detergent and sulfuric acid.

Pigeonite

Pigeonite is a silicate mineral named after Pigeon Point in Minnesota where it was first found. It forms dark green crystals that are found in volcanic rocks on Earth and in meteorites from Mars or the Moon. Those darn pigeons get everywhere...

MEAN

MEAN is definitely a mean molecule. It stands for monoethanolamine nitrate, which is an explosive used as a sensitiser in 'slurry explosives' (mixtures of ammonium nitrate, sodium nitrate, a gelling agent and water). Slurry explosives are sometimes used in mining and quarrying, but nowadays they are on various governments' watch-lists as potential terrorist weapons due to their ease of manufacture. I believe it's also used in small quantities as a fertiliser, and doesn't cost too much - so it's a favourite with mean gardeners.

Duranterectoside

I'm not sure I like the sound of an 'erectoside'...it sounds like it's a sort of reverse-Viagra! Actually it's a type of glucoside derived from the Japanese plant Duranta erecta. There are several different versions, the one shown is duranterectoside A.

Thanks to Bastiaan Vos for suggesting this molecule. For more details see: Y. Takeda, et al, Phytochem. 39 (1995) 829.

Miscellaneous chemical funnies...

Grenville Turner emailed me to say that the name geologists give to a rock or mineral which is impossible to identify is Fubarite, since 'fubar' is the notorious acronym (f**ked up beyond all recognition). And similarly, Kay Dekker emailed me to say that he wished that some geologist or mineralogist called Webbs would get out there and discover 'Webbsite'. Also, Heather Wood tells me that geologists give the name 'leverites' to a rocks that have nothing interesting to distinguish them and only take up room in your backpack. A typical exchange: New Student: What's this? Smart-ass Professor: A leverite. New Student: A leverite? Smart-ass Professor: If I were you, I'd leave 'er right there.

In the same vein, Iain Fielden from Sheffield-Hallam University said:

Metallurgists are also great ones for naming a material, or variant, as something-ite. Classic examples are various forms of steel, Austenite (face centre cubic crystal form, discovered by Austen), ferrite (normal room-temperature body centered cubic form), pearlite (it looks like mother of pearl, but only if viewed through a low quality microscope, such as was the best available in late Victorian/early 20th century times), Bainite and Martensite (different distributions of iron carbide in ferrite, produced by different heat treatments).

When a steel has been heat-treated wrongly, the result is usually a complex (and useless) mixture of at least two of Martensite, Bainite and pearlite. In some labs, these mixed structures are occasionally referred to as "Bagashite" or "Pileashite", though never when the customer is visiting.

Example:Metallurgist 1: (looking through microscope at the suspect piece of metal) "Well, its not the tempered Martensite that the spec. says it should be."Metallurgist 2: "So what is it then?"Met 1: "I think it's Bagashite. Here, you take a look, what do you think?"

"Crockashite" has also been proposed as a generic name for new wonder materials for which poorly substantiated, purely theoretical or somewhat optimistic claims are made. For example:"Of course all this will be superceded when nanotube composites become available""True, but that does pre-suppose that it's possible to produce quality nanotubes, in quantity, and at the right price. Until then, its just Crockashite."

And similarly, Darren Sydenham told me that in Australia the government tertiary education classes were nicknamed 'tech' by the students. In Geology lessons, when asking their lab supervisor about the mineral Tectonite, the students would ask 'Do we have tectonite?'. If the answer was no, they'd all go home!

Eddie Luzik also emailed me to say that in the 1998-9 edition of the Aldrich chemical catalogue there was a strange set of index headers on some pages. These index headers just contain a shortened version of the first chemical name on that page, for ease of searching. On pages 1579, 1580 and 1581 there is tetraKISME, tetraKISSU and then tetrALONE. Maybe this has some deeper meaning for the state of chemists' dating skills... (The full names of the molecules are: [1,2,3,4-Tetrakis(methoxy-carbonyl)-1,3-butadiene-1,4-dyl]palladium, 5,10,15,20-Tetrakis(4-sulfonatophenyl)-21H,23H-porphine manganese(III), and Tetralone. Unfortunately, in the new edition of the catalogue these molecules appear lower down the pages, so they no longer appear in the headers...).

Bill Edmonds told me that Texas A&M University has an acid named after it, called tamuic acid. It's a good job Cambridge University Nano-Technology centre hasn't got a molecule named after it yet...

Naomi Lipsky emailed me and said that she'd once had the good fortune to attend a talk by Sir Hans Krebs. He said one of the questions he oftens gets is: how did he know the Krebs Cycle turned clockwise?

Tavi searched through the Online Mendelian Inheritance in Man database of proteins, and found the following proteins: relaxin, survivin, fidgetin, fukutin, antiquitin, mortalin, prohibitin, herculin, giantin, orphanin, semaphorin, arrestin, defensin, recoverin, cabin, rabin, rasputin, and aladin. And Mark Isaak told me of another protein called stargazin which derives from mutant epileptic mice that just lie and their backs and stare at the stars...

And Professor Anthony Nicholls gave me a link to the Apoptosis Glossary, which is full of weirdly named proteins. Apoptosis is a Greek word meaning 'the dropping of leaves from a tree'. It describes the common morphological changes that characterize the process of cellular self-destruction. The site has many strange names for these proteins and enzymes, including: Bad, Boo, CARDIAK, Casper, CLAP, DEDD, MADD, SODD, TANK, TRAMP, TRANCE, and TWEAK, to name but a few.

and Joe Fortey found some more involved in blood clotting called: tissue factor, convertin, preconvertin, accelerin, thrombomodulin, stuart and christmas.

and Duncan Wiles found a protein which when absent from Arabidopsis results in an altered leaf morphology. For this reason (and probably also for a laugh) its discoverers' termed it Knobhead.

and Helen Webb and Shane Liddelow told me that recently a new kinase enzyme was identified and was called "JAK", which actually stands for JAnus Kinase (named after the 2-faced God Janus since it has two phosphate-transferring domains. Some biochemists also say that JAK stands for "just another kinase".- and similarly, Leon Mathiasen from Arhus University found that in winemaking, lactic acid bacteria is known as LAB...so you can put chemicals into your lab, and put LAB into your chemicals.- and Matthew Nowak of Penn State Uni reminded me about the molecule NAD, which is a funny acronym for unprotinated form of nicotinadmide adenine dinucleotide. It's used in tons of biological reactions as a proton acceptor or donor. (For those of you who don't get the joke, NAD is English slang for testicle).- and Lily Zhou told me about 2 buffers called MOPS (3-(N-morpholino)propanesulfonic acid) and PIPES (piperazine-N,N'-bis-[2-ethanesulfonic acid]), which are presumably used in cleaning... - and Brooke Richardson tells me of another called CHAPS (3-[(3-Cholamidopropyl)dimethylammonio]-1-propanesulfonate)... I assume these are the CHAPS that use the MOPS to clean the PIPES...- and Arjen van Doorn told me of a gene called called the RING gene, which stands for Really Interesting New Gene.

Leon Mathiasen from the University of Aarhus, Denmark, tells me that a famous organic reaction is called the Smiles Rearrangment (right), and organic chemists use it to cheer themselves up after a hard day in the lab.

Within the field of fragrance chemicals there are many strange names, although most of them tradenames. One example told to me by Bo Jensen is 'Montaverdi' for 3(Z)-hexenyl-cyclopropylcarboxylate, marketed by International Flavors and Fragrances. The explanation is that this ester has a fresh, green odor, and that the market abounds with green-smelling chemicals, each with a 'green' tradename. So how to give it a novel green-sounding name? Although Monteverdi was a composer, his name also means 'green mountain'. Voila!

Brandi Baros from Allegheny College, Meadville, PA., told me that she did her graduate work in the lab of Roger Hendrix, who is well-known in the bacteriophage (viruses that infect bacteria) circles for having a sense of humour to go with his great science. Going along with the convention that functional chunks of nucleic acid usually have names ending in -on (for example, the coding group of 3 DNA or RNA bases is a codon, while a group of related genes in bacteria that are translated at once is the operon, and the entirety of DNA that a bacterium replicates is the replicon; in eukaryotes we have the expressed gene sequences known as exons that are interrupted by the intruding introns), he came up with a new name for an odd phenomenon in bacteriophage genomes. He found related phages where one phage's genome had odd insertions than made them have more DNA in certain places than the other phages in the related group. Since these insertions seemed to be somewhat random but caused the phage to have more DNA than its cousins, the insertion was named a "moron". The reference for the paper is: J. Mol. Biol. 299 (2000) 27, from which we get the quote: "To provide a simple way to refer to these DNA segments, we propose to give them the name, moron, to indicate the fact that when one is present in the genome there is more DNA than when it is not present."

Richard Irwin says that an ingredient in many of performance enhancing drinks could be called smartallic or i-nos-it-ol.

And Ken Ruiz emailed me to say that he always found it difficult to tell his wife, Lynne, of his feelings towards her, without thinking he'd had come across a new member of the Penicillin family: I-luv-u-lin.

And on the subject of fictitious names for molecules, Tim Rickard tells me that the fanciful name for the molecule shown on the left is 'doggycene', while David Schmidt tells me that the molecule on the right should be called 'Kermitinol' after Kermit the Frog.

Dr John Moody , from the University of Plymouth, told me that nitric oxide donors are called NONOates of which a good example is spermine NONOate. And he also told me about some nonionic detergents which go by the names of Triton X-100, Lubrol PX, Tween 80 and Brij 35.

Stephen Ashworth from UEA emailed me to say that he has a reagent in his lab called Wanklyn's soap. It was supplied by BDH, and according to the label is flammable and has one degree of hardness! Wanklyn's Soap is an ethanolic solution of some soap which was formerly used to test for water hardness. Thus we have the Wanklyn Scale which was in competition with the Clarke scale.

Jason Masuda from University of California, Riverside, sent me the cartoon below which is taken from a textbook by M. Sclosser [Modern Synthetic Methods" (R. Scheffold, ed.) VCH, 1992, 227-271]. There is a

whole 'zoo' of superbases based on the original molecule called 'Schlosser Base', and each base behaves in different ways and has been given a nickname. The cartoon depicts the characteristics of each base, so n-BuLi/KOtBu (nicknamed 'LICKOR') is the 'workhorse' used for many general reactions, LIC works, but is slow like snail, while 'LICMEDA' is a bit of a lame duck. I'll leave you to guess how the others react based on their animal analogues...

And on a similar animal theme, M. Farooq emailed me with a copy of an article entitled "Old MacDonald Named a Compound: Branched Enynenynols" that was originally published in the J. Chem. Ed. 74 (1997) 782, about what would happen if 'Old MacDonald' were a chemist, and made molecules that have the shapes of animals. Some are shown below.

Tometomo Hamaguchi , a chemistry student at York University, emailed me to say that a standard technique in NMR spectroscopy is called Spin Echo Correlated (or Correlation) SpectroscopY, or SECSY for short. Moreover, Lily Zhou from Michigan University told me that COrrelated SpectroscopY is COSY, FOldover Corrected Correlation SpectroscopY is called FOCSY, Nuclear Overhauser Enhancement SpectroscopY is NOESY, and Insensitive Nuclei Enhanced by Polarization Transfer is INEPT. And Tom Bisschops tells me that there is another NMR experiment which goes by the name INADEQUATE (Incredible Natural Abundance Double Quantum Transfer Experiment). This means you can have FOCSY NMR technicians sitting in their COSY labs creating SECSY spectra for you, while the nearby NOESY, INEPT technician looks at his INADEQUATE results... There's also a link to a list of crazy NMR acronyms, which include: BIRD, CAMELSPIN, CHIRP, CRAMPS, DIGGER, DOUBTFUL, FLOPSY, FUCOUP, GRASP, GROPE, HOHAHA, PRESS, STEAM, STUD, SUSAN, WATERGATE, and WURST.

But I think the best acronym of all for a scientific technique was sent to me by Charlie Bond. It's for Angle-Resolved Spin-Polarised Inverse Photoemission Spectroscopy, or ARSPIPES for short! If you don't believe me, see: Surf. Sci. 377-379 (1997) 229.

And on a related theme, David Louis Proctor from Cornell University tells me that in the field of femtosecond laser spectroscopy, there is a is a family of techniques which allow the measurement of the pulse using a copy of the pulse as a measuring tool. The first of these techniques is Frequency Resolved Optical Gating, or FROG. Another version is GRating-Eliminated No-nonsense Observation of Ultrafast Incident Laser Light E-fields (GRENOUILLE, which is French for frog).And similarly, James Landon tells me that the world of Computational chemistry uses the 'qp matrix' in the calculation of certain molecular dynamics problems. Since 'qp' sounds like Kewpie (the doll maker), the algorithm is called the DOLLS algorithm. This is taken a step further, with the reverse process giving rise to the SLLOD algorithm.

Eric Kaufman from North Carolina State University sent me this reference to a ruthenium compound known short-hand as Ru(Tris)BiPy-on-a-stick (pronounced Rew-Tris-Bip-e on a stick). The picture from the paper must be one of the most suggestive molecular pictures in any Chemistry Journal. [Ref: S.H. Toma, et al, Inorg. Chem. 43 (2004) 3521.]

Charles Turner pointed out that Gerti Cori received the Nobel Prize for her work on carbohydrate metabolism and became the third woman and first American woman to do so. In 2008, the US Post Office recognized her (along with Edwin Hubble, Linus Pauling, and John Bardeen) on a postage stamp, showing her portrait and a molecule, the Cori ester, she discovered. They decided to go ahead and issue the stamp despite the fact that there is an error in the chemical formula for the molecule. In case you haven't spotted it, the error is that the bond to the phosphate group should go to the first O, not the second.

Malcolm Farmer suggested that linoleic acid might be an unsaturated fatty acid extracted from old floor coverings. Actually, this isn't so far fetched, since linoleum is made from linseed oil and finely ground cork, you probably could extract linoleic acid from it.He also said that as an example of the odd organisms that people screen for when looking for new antibiotics (e.g. Streptomyces for streptomycin, Ascomycetes for ascomycin, etc), we have the antibiotic compound rapamycin. It isn't, unfortunately, derived from the ground up practitioners of a particularly annoying musical genre, but from a soil fungus first discovered on Easter Island (Rapa Nui).

Ian Livingstone told me about the soapy molecule called saponin, which he remembered from his school days, together with the question "what's saponin"?

I recently read a paper that thanked an American Foundation for funding the work. It was called the John and Fannie Hertz Foundation. Fannie Hertz!...you couldn't make it up!

Joerg Heim emailed me to say that a very well known german Drosophila geneticist (name omitted for discretion) told him once that he prefers to name the most ugly/lethal mutants after lab-personnel, and the nice ones after his wife (and several nicknames). Charles Turner also found a whole load of genes that have been given silly names, including:

o Lunatic Fringe and Radical Fringe, reported in Science, 273, 19 July 1996.

o Cockeye (also in the Drosophila fruit fly),

o Clootie Dumpling and Currant Bun (http://www.dundee.ac.uk/anatphys/molgenet.htm)

o Exuperantia - Drosophila; an anterior defect mutant named after a Christian slave who was beheaded along with his masters but was, despite his martyrdom and unlike his masters, denied sainthood due to his slave status. (http://sdb.bio.purdue.edu/fly/torstoll/exuper1.htm)

o Faint Sausage - Drosophila heart morphogenesis gene (http://www.neuroscience.ucla.edu/faculty-page.asp?key=50)

o INDY - acronym for 'I'm Not Dead Yet'; a Drosophila mutation which allows it to live twice as long (http://whyfiles.org/shorties/070old_fly/)

o Mothers Against Decapentaplegic and Daughters Against Decapentaplegic - are mutation enhancing Drosophila genes (http://sdb.bio.purdue.edu/fly/newgene/mothadpp.htm)

o Tinman - literally a heartless Drosophila mutant (http://adsr13.mssm.edu/domains/dept/facultyInfo.epl?objname=biomol&user=frascm01)

o ZapA - a gene named for musician Frank Zappa. This gene codes for a protease in the common bacterium Proteus mirabilis. (http://homepage.ntlworld.com/andymurkin/Resources/MusicRes/ZapRes/ZapA.html)

o Snafu - 'Snafu' is an American military acronym for 'Situation Normal All F**ed Up'. In Drosophila, the embryos are initially normal but become progressively abnormal with developmental time and continued cellular mitosis due to the snafu mutation. (http://flybase.bio.indiana.edu/.bin/fbidq.html?FBgn0061481)

o Gleeful - This gene encodes a C2H2 zinc finger transcription factor with high sequence similarity to vertebrate Gli proteins, so the gene has been named gleeful (Ggl).[Furlong et al., Science 293:1632].

o Hamlet - Named for Hamlet's "to be or not to be" soliloquy because it affects development of cells descended from the Drosophila IIB cells. [Science 297:1355].

o Callipyge - is Greek for 'beautiful buttock'. A group at Duke University have isolated the callipyge gene. A mutation in this gene lets sheep convert food into muscle 30 percent more efficiently yielding sheep with "big and muscular bottoms". The bottoms of the sheep which carry this mutant callipyge have very little fat, so the gene could shed light on obesity and fat metabolism.

o Stuck gene - another fly gene which causes the male flies to become stuck in the females after copulation because 'appendages of their terminalia are held in aberrantly protruding positions'. They should be so lucky...

o Pokemon gene - which stands for POK Erythroid Myeloid ONtogenic factor (thanks to Jenni Vedenoja for this one).

and he also found the following in Harper's Magazine (June 2002):

"From Flybase, a database of fruit-fly genes maintained by a consortium of research institutions. The genes were named by the researchers who discovered them. Convention suggests that if the genes' human counterparts are discovered, they will be given the same names:

aloof, always early, amontillado, bang senseless, bang sensitive, bride of sevenless, brother of odd with entrails limited, bumper-to-bumper, couch potato, crack, crossbronx, Daughter killer, daughter of sevenless, Deadpan, deathknell, Dinty, disco-related, dog of glass, effete, eggroll, enoki mushroom, escargot, ether a go-go, fear-of-intimacy, fuzzy onions, genghis khan, glass bottom boat, Godzilla, Grunge, gut feeling, helter-skelter, he's not interested, hoi-polloi, In dunce, inebriated, jekyll and hyde, just odd knobs, ken and barbie, king tubby, klingon, ladybird early, ladybird late, lemming, Lesbian, long island expressway, maelstrom, Malvolio, members only, mozzarella, naked cuticle, nanking, okra, out at first, oxen, pacman, papillote, pentagon, pugilist, quagmire, quick-to-court, redtape, Revolute, roadkill, rolling stone, sawtooth, scab, scott of the antarctic, scruin like at the midline, sevenless, Sex lethal, shank, similar to Deadpan, singles bar, slamdance, spotted dick, stranded at second, super sex combs, Thor, thousand points of light, Trailer hitch, vibrator, viking."

On the same theme, Phill Baker from the University of New Mexico told me about a gene that he worked on in his lab called TINA1, which was named after the undergraduate student Tina Nguyen who was responsible for a large part of the data collected on that gene.

Also, Joe Bobich told me about a particular mutated protein (later called dynamin) in a fruit fly, which was named with an appropriate Japanese word; shibire. However, the Japanese was chosen so that the temperature sensitive form of the "shi" mutation would have to be named shits. (See for example, Guha et al. J. Cell Sci . 116 , (2003) 3373-3386. )

Although it's not a molecule, Leigh Arino de la Rubia told me about a bateriophage (a virus that infects a bacterium) called Corndog, after its unusual shape.

And Charles Turner found this article about a newly discovered element:

New Element discovered

A major research institution recently announced the discovery of the heaviest element yet known to science. This new element tentatively has been named "Corporatium." Corporatium has 1 neutron, 12 assistant neutrons, 75 deputy neutrons, and 111 assistant deputy neutrons, giving it an atomic mass of 312.

These 312 particles are held together by a force called morons, which are surrounded by vast quantities of lepton-like particles called peons. Since Corporatium has no electrons, it is inert. However, it can be detected as it impedes every reaction with which it comes into contact.

A minute amount of Corporatium causes one reaction to take over 4 days to complete when it would normally take less than a second. Corporatium has a normal half-life of 3 years; it does not decay but instead undergoes a reorganization, in which a portion of the assistant neutrons and deputy neutrons and assistant deputy neutrons exchange places.

In fact, Corporatium's mass will actually increase over time, since each reorganization causes some morons to become neutrons forming isodopes. This characteristic of moron-promotion leads some scientists to speculate that Corporatium is formed whenever morons reach a certain quantity in concentration. This hypothetical quantity is referred to as "Critical Morass."

You will know it when you see it...

[There's another version of this, where the densest element is called "Bushcronium", with symbol "Du" for "Dubya". The rest of the article is the same, but then the following is added at the end]:

When catalyzed with money, Bushcronium activates Foxnewsium (Fx), an element that radiates orders of magnitude more energy, albeit as incoherent noise, since it has 1/2 as many peons but twice as many morons.The "nucular" reaction alluded to below, where Du combines with Foxnewsium when bombarded by a moron beam yields: Du + m (morons) + Fx = DumFxwhich is sometimes phonetically pronounced to describe the nature of the isodope produced.

Also, Alain Gottcheiner told me that the element strontium causes amusement in Dutch-speaking countries since in Dutch, 'stront' means 'turd'. It was actually named after the the village of "Strontian" in Scotland, where it was discovered. I wonder if the inhabitants of that village know what the village's name means in Dutch...? In fact, Alan Jackson emailed me to give further info about the name. Strontian - Sron an t-Sithein - means "The Fairy's Nose", the 'Nose' being a peninsula into Loch Suinart. The mineral was discovered in a mine within the nose, back in the days when miners used pickaxes. Therefore Strontium was the only element to have been discovered by picking someone's nose!

Still on the subject of elements, Charles Turner also told me about some examples of element etymology, taken from Isaac Asimov's "Book of Facts":

It would be improper for a scientist to name a discovery after himself. Thus, when the French chemist Paul Emile Lecoq de Boisbaudran discovered a new element in 1874 he named it "gallium" after Gallia, the Latin name for what is now France. However, le coq is "the rooster" in French, and gallus is "rooster" in Latin. There is at least a suspicion that Lecoq de Boisbaudran was doing a little crowing on his own.

Only one of the eighty-one stable chemical is named after a human being. It is gadolinium, which is named for a Finnish chemist, Johan Gadolin, who first studied the minerals from which no less than fourteen elements, including gadolinium, were isolated.

Four of the chemical elements are after the hamlet of Ytterby near Stockholm, where the minerals

containing them were first located. The elements are erbium, terbium, yttrium, and ytterbium. In contrast, France, Germany, Russia, and the United States have one element apiece named in their honor. They are francium (and also gallium, see above), germanium, ruthenium, and americium. Alas, Great Britain has none...except for maybe strontium which, as Sheila Glidewell pointed out to me, was named after the Scottish town Strontian, in the Argyllshire district, where strontium carbonate mineral was first identified in the late 18th century.

Charles Turner also told me about British born neurologist Oliver Sacks' boyhood memoir "Uncle Tungsten - Memories of a Chemical Boyhood". Here are a couple of quotes concerning the proposed names for elements that are amusing:

"In addition to the hundred-odd names of existing elements, there were at least twice that number for elements that never made it, elements imagined or claimed to exist on the basis of unique chemical or spectroscopic characteristics, but later found to be known elements or mixtures: "alabamine", "bohemium"... I was oddly moved by these fictional elements and their names, especially the starry ones. The most beautiful, to my ears, were "aldebaranium" and "cassiopeium" (Auer's names for elements that actually existed, ytterbium and lutetium) and "denebium," for a mythical rare earth. There had been a "cosmium" and "neutronium" ("element 0"), too, to say nothing of "archonium," "asterium," "aetherium," and the Ur-element "anodium," from which all the other elements supposedly were built.Other obsolete or discredited names also referred to actual elements:thus the magnificent "jargonium," an element supposedly present in zircons and zirconium ores, was most probably the real element hafnium.""Although elements 93 and 94, neptunium and plutonium, were created in 1940, their existence was not made public until after the war. They were given provisional names, when they were first made, of "extremium" and "ultimium," because it was thought impossible that any heavier elements would ever be made. Elements 95 and 96, however were created in 1944. Their discovery was not made public in the usual way---in a letter to NATURE, or at a meeting of the Chemical Society---but during a children's radio quiz show in November 1945, during which a twelve-year-old boy asked, "Mr. Seaborg, have you made any more elements lately?"

Charles Turner also told me that, according to the November 2005 issue of Discover magazine, Seaborg named his newly discovered element 94 Pluto after the recently discovered (and even more recently demoted) planet Pluto. "Seaborg chose the letters Pu as a joke, which passed without notice into the periodic table." (Since PEEEE-YEEWWW is an interjection indicating a bad stench).

Staying with Seaborg(ium), not only was [Glenn] Seaborg the first living scientist to have an element named after him, he was the only person who could have received mail addressed only in elements: Seaborgium, Lawrencium (for the Lawrence Berkeley Laboratory where he still works), Berkelium, Californium, Americium. But don't forget the zip code." - Jeffrey Winters, Discover Magazine, January 1998. Kay Dekker recently pointed out to me that Seaborg isn't alone in being able to be addressed by elements: Ève Curie (Marie and Pierre's younger daughter) could almost certainly have been reached after World War II in Paris, where she was the co-publisher of the Paris-Press newspaper, with the address "Curium, Lutetium, Francium". Curium had been discovered in 1944; lutetium was named after Lutetia, the Latin name for Paris, and Francium was named after France.

...and also on the theme of element names, this is from the online encyclopedia Wikipedia: "Also called Radium F, polonium was discovered by Marie Curie and Pierre Curie in 1898 and was later named after Marie's home land of Poland. Poland at the time was under Russian domination, and not recognized as a nation. It was Marie's hope that naming the element after her home land would add noteriety to its plight. Polonium may be the first element named to highlight a political controversy."

Thomas Schneider from the National Cancer Institute in Maryland told me about a protein called Dam Methylase, which is part of the 'dam modification gene' of E. coli. And Mirela Matecic has been working with a whole series of yeast proteins called SIR. The are know as 'Sir Silencer' molecules because they are involved in silencing and repression, although they sound more like one of King Arthur's Knights of the Round Table. Another strangely-named protein is called 'the DEAD box' after its amino acid conserved sequence (emailed to me by Israel Barrantes).

Jenny Allcock told me that her biology textbook was called "Living Things" and was written by the appropriately named author V. Slaughter.

Andy Mance used to work with a solvent called Fat Brown B, which sounds like the name of a jazz singer. It is also called by its less jazzy name of Solvent Red 3, and its formula is C18H16N2O2.

Andy Wigginton from the University of Kentucky says that they sometimes deal with a group of pollutants that can be released from underground gasoline storage tanks. These include Benzene, Toluene, Ethylbenzene, and Xylene, which they abbreviate as B-TEX, which sounds like an invocation to become a cowboy. When they are just concerned with the last three pollutants, they are simply TEX (somehow it seems appropriate that a gasoline-derived group of pollutants should be so associated with home of the current US President).

Lars Finsen tells me that the octafluoroxenates with the anion XeF82- are the most stable noble gas

compounds known. But if any analogous krypton compounds were ever made, they would probably be called fluorokryptonates in the higher oxydation stages and fluorokryptonites in the lower oxidation stages, in accordance with traditional nomenclature - for instance, sodium tetrafluorokryptonite, Na2KrF4. He says that this might possibly be a useful substance to have around if you were planning to rob a bank in Metropolis? Tue Bruun Petersen, however, thinks that the name kryptonite would have been given to the anion KrO2

2- before IUPAC nomenclature was enforced.Recently it was reported that new mineral has been identified in a mine in Serbia that has the same chemical formula as Superman's kryptonite - sodium lithium boron silicate hydroxide. This is same scientific name that was written on a case of rock containing kryptonite stolen by Lex Luthor from a museum in the film 'Superman Returns'. The new mineral does not contain fluorine (which it does in the film) and is white rather than green but, in all other respects, the chemistry matches that for the rock containing kryptonite. Unfortunately, the mineral cannot be called kryptonite under international nomenclature rules because it has nothing to do with krypton gas. Instead, it will be formally named jadarite since Jadar is the name of the place where the Serbian mine is located.

On the same theme, Christian Thøgersen told me that the photo below comes from an actual Periodic Table, which features the applications of the various elements in its various states and forms. It looks like somebody put in the extra description of krypton for fun, and it went unnoticed until some undergraduate with a digital cam found it.

Charles Turner has also found a link to the chemical with the longest name in a scientific Journal. It is the 1,913 character long, 267 sequence amino acid, and is the full name for Tryptophan Synthetsase:

methionylglutaminylarginyltyrosylglutamylserylleucyl phenylalanylalanylglutaminylleucyllysylglutamylarginyl lysylglutamylglycylalanylphenylalanylvalylprolylphenyl alanylvalylthreonylleucylglycylaspartylprolylglycylisol eucylglutamylglutaminylserylleucyllysylisoleucylaspartyl threonylleucylisoleucylglutamylalanylglycylalanylaspartyl alanylleucylglutamylleucylglycylisoleucylprolylphenyl alanylserylaspartylprolylleucylalanylaspartylglycylprolyl threonylisoleucylglutaminylasparaginylalanylthreonylleucyl arginylalanylphenylalanylalanylalanylglycylvalylthreonyl prolylalanylglutaminylcysteinylphenylalanylglutamyl methionylleucylalanylleucylisoleucylarginylglutaminyllysyl histidylprolylthreonylisoleucylprolylisoleucylglycylleucyl leucylmethionyltyrosylalanylasparaginylleucylvalylphenyl alanylasparaginyllysylglycylisoleucylaspartylglutamylphenyl alanyltyrosylalanylglutaminylcysteinylglutamyllysylvalyl glycylvalylaspartylserylvalylleucylvalylalanylaspartylvalyl prolylvalylglutaminylglutamylserylalanylprolylphenylalanyl arginylglutaminylalanylalanylleucylarginylhistidylasparaginyl valylalanylprolylisoleucylphenylalanylisoleucylcysteinyl prolylprolylaspartylalanylaspartylaspartylaspartylleucyl leucylarginylglutaminylisoleucylalanylseryltyrosylglycyl arginylglycyltyrosylthreonyltyrosylleucylleucylserylarginyl

alanylglycylvalylthreonylglycylalanylglutamylasparaginyl arginylalanylalanylleucylprolylleucylasparaginylhistidyl leucylvalylalanyllysylleucyllysylglutamyltyrosylasparaginyl alanylalanylprolylprolylleucylglutaminylglycylphenylalanyl glycylisoleucylserylalanylprolylaspartylglutaminylvalyllysyl alanylalanylisoleucylaspartylalanylglycylalanylalanylglycyl alanylisoleucylserylglycylserylalanylisoleucylvalyllysylisol eucylisoleucylglutamylglutaminylhistidylasparaginylisoleucyl glutamylprolylglutamyllysylmethionylleucylalanylalanylleucyl lysylvalylphenylalanylvalylglutaminylprolylmethionyllysyl alanylalanylthreonylarginylserine.

A full description of this molecule and the history of its name is given at http://www.quinion.com/words/qa/qa-imm1.htm

On the same topic of long molecule names, he also tells me that 6,8-DidEeoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-D-galacto-octapyranoside (75 letters and 15 hyphens, total 100 characters) is found in the OED2, although not as a vocabulary entry. Instead it appears in a citation for the word 'lincomycin'.

Charles Osborne tells me that Monsanto produced the early Light Emitting Diodes back in the sixties from gallium arsenide - GaAs. Apparently they couldn't resist calling their products: GaAs Lites!

Wayne Povey from Keele University said that one molecule name that makes him chuckle is methylisobutyl ketone abbreviated to MIBK, which always makes him think of Men in Black: Agent K, played by Tommy Lee Jones.

Graham Sewell remembers that during his undergrad days at Sussex University someone had graffitied the following slogan on wall of the stage 3 cargo lift in the Chemistry Dept: "Potassium Ethoxide rules, C2H5OK"

Staying with schools, Mole Day is an unofficial holiday celebrated among chemistry students in North America on 23rd October, between the hours of 6:02 am and 6:02 pm. This is because in the American style of writing dates it is 6:02 10/23, which resembles the Avogadro constant 6.02x1023 (number of atoms in a mole). There is also a Pi Day (March 14, 3/14), a Square Root day, and a Towel Day (a tribute to Douglas Adams and the Hitchhiker's Guide to the Galaxy).

Plutonium Page Sebring from the University of New Mexico likes the idea of reverse polarity organic reactions, which go by the silly name of 'Umpolung reactions'. It sounds a bit like one of the songs sung by the Oompa–Loompas (photo right) in the original film 'Willy Wonka and the Chocolate factory'.She also tells me about a human protein which mediates the transbilayer movement of plasma membrane phospholipids, and is called 'Scramblase'. Presumably it got its name because sometimes it gets the transfer wrong, and scrambles the order of the lipids...?

Charles Turner has sent me the definition of the mineral Cactolith, which is: "A quasi-horizontal chonolith, composed of anastomising ductoliths, whose distal ends curl like a harpolith, thin like a sphenolith, or bulge discordantly like an akmolith or ethmolith." This definition was coined by the US Geological Survey geologist Charles Butler Hunt, as a satirical jab at the absurd geological terms that were proliferating faster than rabbits, and at the many geologists who seemed to be taking themselves too seriously. He later went on to publish the books "How to collect Mountains" and "Dating mining camps with tin cans and bottles". [Ref: C.B. Hunt, Geology and geography of the Henry Mountains region, Utah, 1953].

Anthony Saglimbeni says that at Grad school, they used to call Sodium Methoxide by the nickname 'Naomi' (Na-OMe), so that you'd add a pinch of Naomi to a reaction and watch it go!

Neil Brookes emailed me to say that in the 1970's there was a filtration-aid called Dicalite (which gave rise to 'She was only the chemist's daughter, but she set your....', etc).

John Wolstenholme emailed me to say that he remembered a Professor at Oxford who once synthesised a Mo compound containing some olefinic and amine ligands, and (unsuccessfully) tried to get it named 'ene amine

amyne a Mo'. And similarly, Matt Jandreau told me that one of his professors mentioned a new molecule (structure, right) in organic chemistry. He said "Old McDonald made this molecule... ene-yne-ene-yne-one".

John Wright told me that in the 1960s there was a report of Kryptic acid (Science 142 242, 1964), but no-one ever managed to repeat the work, and it is now treated as an error.

Gary Randall emailed me to suggest Oleic acid , and said that it was often called Bullfighter's Acid. Geddit?

Joe Kosmoski told me the following: "Several years ago, I was lucky enough to sit in on a Seminar titled 'Dog CRAP'. Most Chemists know that CRAP stands for Crude Reagent and Products, and that iron (Fe) is know as the dog metal. Hence when conducting reactions with iron, one would expect to find plenty of Dog CRAP." And on a similar theme, John Lamper suggested that the chemical formula for dog's urine should be K9P, while David Govett said that its chemical name should be fidourine (Fido-Urine).

And on the subject of acronyms, Joe Davidson from the University of Michigan came up with the following common abbreviations for molecules: TEA (Triethylamine, an organic Bronsted base), TIPS (Tri-isopropylsilane, a protecting group for alcohols), MOM (Methoxymethane, or methoxymethyl, an ether that also protects alcohols), and COD (1,4-cyclo-octadiene, a common ligand for many transition metals, that ironically has a potent odour of fish). Kevin Anderson also suggested that mercaptoundecanol can be abbreviated as MUD. Must be a messy synthesis...

HI-O Silver is a wonderful inorganic compound suggested by Michael Klemmer, although I don't think it actually exists. If it did, it would surely be the Lone Ranger's favourite molecule. For those of you who don't remember this classic TV series, the Lone Ranger rode a horse called Silver, and his catch phrase was "Hi-O-Silver...away!" I haven't yet found a molecule called Tonto, though... [Thanks to John H. Havener, Jr for the formula.]

Carl Kemnitz and Michael A. Bailey both told me that barbituric acid was named by its discoverer, Baeyer, after a barmaid named Barbara with whom he was enamoured. There are two additional "Barbara" molecules that are of interest: barbaralane and barbaralone. But barbaralane is not named after the street on which Barbara lived. The barbaralone is a bit more depressing whether you interepret it as barbara-alone or barber alone (bad business).

Bert Ramsay tells me that he developed a hypothetic molecule called E-cubane, named after the artist MC Escher, who was renown for his 3D pictures of 'impossible' structures and buildings'. E-cubane is an 'impossible' version of cubane, as you can see from the image right.

Adam Hill told me about fictitious molecules called 'propyl people ethers' after the novelty song, "Purple People Eaters" written and performed by Sheb Wooley (1921-2003), that reached #1 in the US pop charts in 1958.

Chemists have always had a problem with pronunciation...why should anion be pronounded an-ion, and not ay-neon (like onion)? And what about cation and dication, why pronounce them die-cat-ion, not die-cayshun as it should be in normal English rules? And if there's no charge at all, it's unionised...now is that un-ionised or union-ised? [Thanks to Peter Rice for this last one].

Carl Kemnitz also tells me that conceptually, the most hilarious journal article title that he's come across was "Stiff and Sticky in the Right Places: The Dramatic Influence of Preorganizing Guest Binding Sites on the Hydrogen Bond-Directed Assembly of Rotaxanes." Rotaxanes, by their very nature are pure innuendo since they are rod-like molecules that are thrust through the hole of a cyclic structure (imagine demonstrating the concept by placing your index finger of one hand through the hole in the other hand made by the "OK" symbol). What makes things better is that one of the authors' names was Teat and another Wong. How this made it past the editors of JACS, I don't know. The reference is: J. Am. Chem. Soc. 123 (2001) 5983.

And on the subject of curiously named authors for papers, I can cite one of my own papers about the Chemistry of Space Dust, whose authors were: D.R. Flower, G. Pineau des Forêts, D. Field and P.W. May, Mon. Not. R. Astron. Soc. 280 (1996) 447, i.e. the very Spring-like: Field, Forest, Flower and May!

Continuing the theme, Sikke M. Kingma from Leiden University told me: "I was reminded of a paper known in 'my' field (theoretical chemistry/chemical physics) containing tables with detailed numbers describing "Bounds to Two- and Three-Body Long-Range Interaction Coefficients for S-State Atoms" (J. Chem. Phys., 83, (1985) 3002 ), with authors called (J.M.) Standard and (P.R.) Certain."

And still on the same theme, Daniel Shane from Cambridge University tell me that George Gamow and his student Ralph Alpher once wrote a famous cosmogenesis paper, and Gamow put Hans Bethe's name on it as well, just so it would be by Alpher, Bethe and Gamow (alpha, beta and gamma). It is further alleged that Gamow tried to persuade another scientist (R.C. Herman) to change his name to Delter, and come in as a fourth author, to add to the joke. I belive the paper was published in the Physical Review on April 1, 1948.

And yet more on the same theme, there are 4 papers by an American/Italian group who, for a joke, added a fictitious author by the name of Stronzo Bestiale, which means 'brutal/beastly turd'. The refs are: Hoover W.G., Posch H.A., Bestiale S., J. Chem Phys. 87 (1987) 6665; Moran B., Hoover W.G., Bestiale S., J. Stat. Phys. 8 (1987) 709; W.G. Hoover, H.A. Posch, B.L. Holian and S. Bestiale, Bull. Am. Phys. Soc. 32,(1987) 824; and W.G. Hoover, B. Moran, B. Holian, H. Posch and S. Bestiale, Bull. Am. Phys. Soc. 32, (1987) 1370. Stronzo Bestiale is allegedly affiliated to the Institute for Advanced Studies at Palermo, Sicily, which is fictitious. [Thanks to Fabio Pichierri and David Richerby for some of this info].

And yet more on the same theme, there are a number of papers in journals by authors named Yin and Yang. A chemistry related one is: Yin C. and Yang C.Z. J. Appl. Polymer Sci, 82 (2001) 263.

Another Journal curiousity: In the Journal called Physical Chemistry Chemical Physics, which is often abbreviated as PCCP, there was a paper published entitled "PCCP does exist" about the P-C-C-P molecule. [PCCP , 2(10) , 2000, 2245. ]

Jerry Van Cleeff emailed me to say that it was curious that the organic molecule named Fluorene (C13H10) doesn't contain the element Fluorine. He also said that he'd heard that "Scientists in Pisa, Italy, have discovered a possible reason why the Leaning Tower cannot be fixed - the soil around the tower contains the aromatic compound Azulene" Geddit?

David Bradley has created a fun website called The Chymical Wedding all about how chemicals are used in life, weddings and marriage.

and Thomas Jeanmaire gave me the link to the wonderful environmentally active web site to do with banning the dangerous chemical 'Dihydrogen Monoxide'.

Bob Lidral told me about the fictitious molecule thiotimoline, which was invented by the Sci-Fi author Isaac Asimov as a joke. He wrote a spoof article describing experiments with thiotimoline, and said that was so soluble that it dissolved in water up to 1.3 seconds before the water was added! The full story of the spoof is here, and the full article by Asimov is here.

Malin Dollinger , a cancer physician from LA, told me that there are two drugs that are used to to bring back patients who are hopelessly ill with cancer. These drugs are known by their nicknames in humorous exchanges among cancer physician colleages, as Resurectine and Lazarine.

And on the subject of fictitious drug names, Charles Turner sent me the following:

"In Pharmacology all drugs have two names - a trade name and a generic name. For example, the trade name of Tylenol has a generic name of acetaminophen (or paracetamol in the UK). Aleve is also called naproxen. Amoxil is also called amoxicillin and Advil is also called ibuprofen.The FDA has been looking for a generic name for Viagra. After careful consideration by a team of government experts, it recently announced that it has settled on the generic name of mycoxafloppin. Also considered were : mycoxafailin, mydixadrupin, mydixarizin, mydixadud, dixafix, and of course, ibepokin."

Christopher C. Wells , Anne Gorden and Vincent Schüler have sent me a huge list of molecules named after places...himalayamine, pakistanamine, americanin, ecuadorin, grenadadiene, virginiamycin, mauritiamine, alaskene, texaphyrin, alaskaphyrin, taiwanins, montanastatin, mediterranenols, bahamamide, arizonins,

pacifenol, brazilin, argentinine, guyanin, jamaicin, louisianins, floridanolide, oregonenes, utahin, michigazone , ukrain, malaysic acid, thailandine, mongolicains, vanuatine, australinols, tasmanine, vietnamine, angolamycin, gabonine, senegalene, madagascarin, tanzanene, ugandoside, yemenimycin, syriamycin, jordanine, atlantone, mexicanolide, panamine, albanols, srilankenyne, seychellogenine and borneol. But there doesn't appear to be a molecule named after Britain...?

David Vogel informed me that in his lab, they often say "Did you take your Dumacium today?" when someone does something stupid. He also thinks it would make an appropriate name for a placebo. On a similar theme, Lynton Cox told me that he once sent a know-it-all technician to look for some Tedium sulphate and Euphorium nitrate. And he's still waiting for someone to discover a super metal for musical instruments Didumdidumdium! He also says that chemists synthesise precipitates all the time but he's have never seen precipitic acid.

Speaking of placebos, Paul Bohn from Mount Sterling, OH, USA sent me the following extract from a book called The Throwing Madonna: Essays on the Brain.

"Placebos raise a problem in these days of the pharmacist labeling pill bottles with their contents. One cannot admit that the pill is nothing but sugar if it is to work, so a fancy brand name is needed. Among the proposals made in the scientist's humor magazine The Journal of Irreproducible Results for what to name a brand-name placebo are Confabulase, Gratifycin, Deludium, Hoaxacillin, Dammitol, Placebic Acid and Panacease." Apparently, 'obecalp' is also used as well.

James Fieldsend sent me this chemistry one-liner, which would make a nice email quote: "If you're not part of the solution, you're part of the precipitate."

And Andy told me about a conversation he'd had with a young chemistry pupil, who asked him what 'borax' was. Not wanting to be sidetracked at that precise moment he answered, "It's what a Japanese carpenter says when he hits his thumb with a hammer."

And finally, a chemical joke sent in by Richard H McCaffrey:

Did you hear about the chemist who walked into a pub and asked for a pint of adenosine triphosphate? The bartender said "Sure thing...that'll be ATP, please." (80p in English money, geddit?)

Chemical songs, poems and limericks

Probably the most famous chemistry song is 'The Elements' by Tom Lehrer in which he recites the name of every chemical element to the tune of Gilbert and Sullivan's 'Modern Major General'. There's also a version of this song (The Drugs Song) by Drs Suman Biswas and Adam Kay, but reciting the names of common chemicals and medical drugs. These guys have also written a song about the ultimate medical drug: Paracetamoxyfrusebendroneomycin

David Bradley emailed me to point out a collection of popular songs whose lyrics have been altered to turn them into chemistry songs.

And Anthony Shireman told me that his Biochemistry professor sings some crazy songs that are biochemistry related at the end of every term.

Here's a little limerick, sent in by Gregory Bond.

"A mosquito was heard to complainthat a chemist had poisoned his brain.The cause of his sorrowwas paradichloro-Diphenyltrichloroethane!

And another little ditty, sent in by Garry Heather from Sony.

"Ernie was a chemist,now Ernie is no more.For what he thought was H2O, was H2SO4."

Here's a ditty that was taught to Jerry Goodenough by his Chemistry teacher.

Poor Jimmy, finding life a bore,Drank some H2SO4.Jimmy's father, an MD,Gave him CaCO3.

Now he's neutralised, it's true,But he's full of CO2. [The last line to be interrupted by a burping sound!]

Here's a limerick sent to me by Ian Livingstone.

There was a young chemist from Ryde,Who drank a foul poison and died.It was ortho-hydroxy-para-methoxy-tri-nitro benzaldehyde!