VIBRO CHOLERAE

PUTRESCINE

CADAVERINE

H2N – CH2 – CH2 – CH2 – CH2 – NH2

H2N – CH2 – CH2 – CH2 – CH2 – CH2 – NH2

CHOLERA BACTERIUM

(1,4-diaminobutane or butanediamine)

(1,5-diaminopentane or pentanediamine)

are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses.

two compounds are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis.

also found in semen and some microalgae, together with related molecules like spermine and spermidine.

PUTRESCINE & CADAVERINE

SPERMINEH2N – (CH2)4 – NH – (CH2)3 – NH2

SPERMIDINEH2N – (CH2)3 – NH – (CH2)4 – NH – (CH2)3 – NH2

First isolated from human seminal fluid, were they are highly concentrated

NITROGEN – containing

functional groups

AMINES

MELAMINE

1,3,5-triazine-2,4,6-triamine 

Amines are organic compounds and a type of functional group that contain nitrogen as the key atom.

Structurally amines resemble ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups.

Amines are central in organic chemistry. All known life processes depend on AMINO ACIDS, each of which contains an amine group.

AMINES

N

R2

R1 R3

CLASSIFICATIONS

PRIMARY

R – NH2An amine having one alkyl or

aromatic group bonded to nitrogen.

EXAMPLES

CH3 – NH2 methylamine

CH3 – CH2 – NH2ethylamine

SECONDARY

R2 – NHAn amine having two alkyl or

aromatic groups bonded to nitrogen.

EXAMPLESCH3 – NH – CH3dimethylamine

CH3 – CH2 – NH – CH3

ethylmethylamine

TERTIARY

R3 – NAn amine having three alkyl or

aromatic groups bonded to nitrogen.

EXAMPLESCH3 – N – CH3

CH3

trimethylamine

CH3 – CH2 – N – CH3

CH3

ethyldimethylamine

PREPARATION

WATER HEMLOCK

H │N CH2 – CH2 – CH3

CONIINE

Extremely toxic ALKALOID

OPIUM POPPY

O

N

CH3

OH

MORPHINE

Painkillers with strong hallucinogenic & addictive side effects

CH3│N

O║COCH2CH3

DEMEROLPainkillers similar structure to morphine

but less side effects

COCA

N CH3

O║COCH3

O ║O ─ C ─COCAINE

CACTUS

CH2 – CH2 – NH2

OCH3 CH3O

OCH3

MESCALINE

DART FROG

H3C

H2C

HO

HO

O

H

O NCH3

HCH3

O

C═ O

H3C

CH3

NH

BATRACHOTOXIN

Derived from D’ word BATRACHOS greek means FROG

GALAPAGOS

GUANIDINE

H2N – C – NH2

NH║

Guano deposits on GALAPAGOS Islands.GUANIDINE is the compound by which migratory bird excrete waste

Metabolic nitrogen.

USES

NN

CH2 – CH2 – NH2

H

HISTAMINE

Causes many of the symptoms of common cold and the itchy bump cause by insects bites, the effects of HISTAMINE

can be relieved to some extent by ANTIHISTAMINES…..

CH

O CH2 – CH2 – N CH3

CH3

diphenhydramine (BENADRYL)

C – CH2 – NH – CH3

OH

HO

HO H

EPINEPHRINE

Phenylpropanolamine

CH – CH – NH2

OH CH3

NH

SO2

SACCHARIN

Artificial sweeteners 100 times sweeter than table sugar

NOMENCLATURE

NOMENCLATURE The nomenclature of amines is

complicated by the fact that several different nomenclature systems exist, and there is no clear preference for one over the others.

The most important thing to remember is when to use the following :

1. amine 2. amino 3. aniline

RULE # 1 SIMPLE AMINES - can be

named by common nomenclature as ALKYLAMINE in which amine is added to the name of the organic group.

IUPAC NAMING – Is done by dropping the – e – of the alkane parent chain then add AMINE.

EXAMPLESCH3 – NH2

methylamine

CH3 – CH2 – NH2

COMMON

IUPAC methanamine

ethylamineCOMMON

IUPAC ethanamine

EXAMPLESCH3 – NH – CH3 dimethylamine

CH3 – CH2 – NH – CH3ethylmethylamine

CH3 – CH2 – N – CH3

3HC

ethyldimethylamine

CH3 – N – CH3

CH3trimethylamine

EXAMPLESNH2

cyclopentanamine

NH2

CH3

2 – methyl – cyclopentanamine

NH2

Cl

Cl

Cl

2,4,6 – trichloro – cyclohexanamine

EXAMPLES

CH3 – C ═ CH – CH – CH3

NH2CH3

4 – methyl – 3 – penten – 2 - amine

CH3 – C ═ CH – CH – C ≡ CH

CH3 – CH2 NH25 – methyl – 4 – hepten – 1– yne – 3 - amine

RULE # 2 To name a substituted amine,

both the name and the location of the substituent must be identified.

Substituent on a carbon chain are located by a number, whereas those on a nitrogen are identified by a capital italic letter – N – .

EXAMPLESNH – CH2 – CH3

N – ethyl – cyclobutanamine

NH – (CH2)5 – CH3

CH2 – CH3

CH3 – (CH2)3

3HC

N – hexyl –3 – butyl – 6 – ethyl – 4 – methyl – cyclooctanamine

CH3 – CH2 – CH – CH2 – CH3

EXAMPLES

CH3 – CH2 – N – (CH2)3 – CH3

N – butyl –N – ethyl – 3 – pentanamine

CH3 – CH2 – N – (CH2)7 – CH3

CH3

N – ethyl –N – methyl – octanamine

RULE # 3 AMINE AS SUBSTITUENT NH2 – functional group is

treated as a chain substituent we called them as amino group and the amine is named as a derivative of the parent compound

following the IUPAC rules.

CH3 – CH2 – CH – CH2 – CH3

EXAMPLES

NH2 3 – aminopentane

CH2 – CH2 – CH2

NH2 OH

3 – amino – 1 – propanol

CH2 – CH2 – CH2

NH2 NH2

1,3 – diaminopropane

EXAMPLES

NH2

HO

3 – aminocyclohexanol

CH3 – CH – CH – CH2 – CH2 – OH

NH2

CH2 – CH2 – CH3

3 – amino – 4 – methyheptanol

RULE # 4 AROMATIC AMINES Are usually given names (both common &

IUPAC name) based on aniline, the simplest aromatic amine.

Substituted anilines are named using an italic capital – N – to indicate the attached alkyl group to NITROGEN.

Substituents attached to aromatic ring are named based on the usual way we name them.

EXAMPLESNH2

aniline

NH – CH3

N - methylaniline

NH – CH3

N – methy – 3 – ethyllaniline

CH2 – CH3

PHYSICAL PROPERTI

ES

Low Molecular Weight AMINES are gases at room temperature that possess a characteristic ammonia smell.

Complex Molecular Weight AMINES are either liquid or solid at room temperature having a distinctive "fishy" or extremely foul decomposing smell.

Primary & Secondary amines are usually exhibit lower boiling points compare to tertiary and more complex structure amines.

Amines with fewer than six carbon atoms are generally soluble in water as the result of hydrogen bond formation between amine functional group and water.

ONLY ONE OF ITS KIND

CHEMICAL

PROPERTIES

IONIZATIONGEN.

FORMULAAMINE + Water ↔ Alkyl ammonium ion + Hydroxide ion

Example

CH3 – NH2 + H – OH CH3 – NH3 + + OH ־

methylamine methylammonium ion

Hydroxide ion

EXAMPLESNH2

aniline

+ H – OH

NH3+

Anilinium ion

+ OH ־

Hydroxide ion

CH3 – NH – CH3 + H – OH

dimethylamine

CH3 – NH2+ – CH3

dimethylammonium ion

+ OH ־

NEUTRALIZATIONGEN.

FORMULAAMINE + Acid ---→ Amine salt

Example

CH3 – NH2 + H – Cl CH3 – NH3+ Cl ־

methylammonium chloridemethylamine

EXAMPLE

CH3 – CH2 – NH2

ethylamine

+ CH3COO – H

Acetic acidCH3 – CH2 – NH3+ CH3COO ־

ethylammonium acetate

EXAMPLE

CH3 – (CH2)5 – NH2

hexylamine

+ C6H5COO – H

benzoic acidCH3 – (CH2)5 – NH3+ C6H5COO ־

hexylammonium benzoate

AMIDES