Amines & Amides

The Nitrogenous Organic Compounds!

Let’s do Amines first

• Amines are derivatives of ammonia• one or more of the H’s have been replaced by an

aromatic or alkyl group (R)

Naming amines

• Amines can be primary, secondary, or tertiary (exs)

• common names-draw these:– methyl amine, tert-butyl amine, diethyl amine, ethyl

methyl propyl amine, methyl phenyl amine

• IUPAC names-draw these:– aminomethane, 2-aminobutane, 1,3-diaminopropane,

2-aminocyclohexanol

Aromatic amines

• When one of the R’s is benzene, amines can be named as a derivative of aniline

• draw: – aniline, N-methylaniline, N,N-diethylaniline,

N-ethyl-N-methylaniline

– “N” means the group is attached to a nitrogen

• NH2 can also be used as a side group

– 2-aminobutane also called butanamine

• Amines are some of the most biologically active compounds– bioregulators, neurotransmitters, defense

mechanisms

• many have been developed synthetically for use as drugs and pesticides

Amines as neurotransmitters

• Just read page 513 bottom-516 top• this is some really cool info on how amines play a

role in your brain’s ability to function• norepinephrine, serotonin, dopamine-all are impt

• also read the box on p. 516 about Parkinson’s Disease

Drugs to know-most of which are amines

• Novocain-anesthetic• Cocaine-bad • epinephrine-adrenaline (fight/flight)• amphetamine-stimulant

– derivatives of amphetamine are the amphetamines-stimulate the CNS

• nicotine-insecticide• niacin-vitamin• piperazine-kills intestinal worms• diphenhydramine-Benadryl

• mescaline-hallucinogen• histamine-dilates blood vessels• morphine-pain killer, opiate• scopalamine-prevents motion sickness (?)

– cruise ship story• codeine-cough suppressant• heroin-bad stuff• methadone-synthetic heroin• phenergan-treats nausea• imitrex (sumatriptan)-for migraines• dramamine-motion sickness• propanolamine

Alkaloids

• These are basic comps obtained from plants– can come from leaves, bark, flowers, fruits,

roots

• for many years, tribes knew that physiological effects could be obtained from eating or chewing these substs

• some cured diseases, some were addictive, some killed people

• Abt 1800, chemists began to extract these substances from plants-they discovered that they were bases and called them “alkaloids”

• Generally alkaloids have common names taken from their parent plants

• generally end in “-ine”

story

• 1870 Bayer took urea and malonic acid (from apples) and put them in a test tube. He named the product barbituric acid after his girlfriend Barbara

• That’s where barbituates got their name

Physical/chemical props of amines

• N has 5 electrons in outer shell-3 bonded, 2 extra• N is a base-can donate electron pair (Lewis theory)

• amines react with inorganic acids to form salts in neutralization rxns

• most drugs have been neutralized with acids– if not, they’re called a free base (hippy thing)

• they are salts-why?• More soluble in body fluids

– pseudoephedrine HCl (Sudafed)

• the most obvious property of amines is their odor

• Smaller amines smell like ammonia

• raw fish contains low molecular weight amines– Fish malodor syndrome– Crappie, bream, bass, catfish smells

• larger amines smell worse– putrescine (1,4-diaminobutane)– cadaverine (1,5-diaminopentane)

• nasty beef tips story

Amides

• Amides are derivatives of CA’s (carboxylic acids)

• Naming amides is easy

– ethanamide (IUPAC) acetamide (common)

– methanamide (IUPAC) formamide (common)

• When H’s in the amino group are replaced by R’s, N is used

– N-ethyl methanamide (or formamide)

– N,N-dimethyl ethanamide (or acetamide)

• Amides are found in proteins, they hold amino acids together

• Specific amides that are drugs:

• Diazepam (valium)-tranquilizer

• Ampicillin-antibiotic

• Thalidomide-used to treat nausea in pregnant women-caused birth defects such as flippers on feet and hands

• still has some medical uses in nonpregnant women

Physical Props of Amides

• B/c amines are basic, we would expect amides to also be basic

• But they’re actually neutral-Why?

• b/c the basic N atom is balanced by the acidic carbonyl group

• unsubstituted amides (those w/NH2’s) have high mpts b/c of lots of hydrogen bonding between the molecules

• When “things” replace the H’s, fewer H’s are available for hydrogen bonding and these compounds have lower melting points

Rxns of Amides• Amides undergo hydrolysis• amide + HOH ---> carboxylic acid + salt

• or

• amide + HOH ---> carboxylic salt + amine

• Which one depends on the catalyst-just know that a salt is always formed

• Amide hydrolysis is vital to the digestion and breakdown of proteins in the body. Here the catalysts are enzymes.

Miscellaneous Stuff

• What does OTC mean?– Over the counter

• What happens to your vitamin B6 level when you drink alcohol?– It drops-alcoholics can have deficiency p. 524

• When a pregnant woman takes drugs, how do they get to the baby?– Through the placental barrier

• Nylon is a polymer-a polyamide-remind me to make it

• Amide linkage-where the C and N are bonded in an amide

And a little more

• Acetaminophen is an amide (Tylenol)

• doesn’t irritate stomach like aspirin can

• is an analgesic (pain-killer)

• is an antipyretic (fever-reducer)

• has no anti-inflammatory action

• has been linked to liver and kidney damage

The end

• No more Chem II notes-how sad!