VIBRO CHOLERAE

PUTRESCINE CADAVERINE H 2 N – CH 2 – CH 2 – CH 2 – CH 2 – NH 2 H 2 N – CH 2 – CH 2 – CH 2 – CH 2 – CH 2 – NH 2 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

SPERMINE H 2 N – (CH 2 ) 4 – NH – (CH 2 ) 3 – NH 2 SPERMIDINE H 2 N – (CH 2 ) 3 – NH – (CH 2 ) 4 – NH – (CH 2 ) 3 – NH 2 First isolated from human seminal fluid, were they are highly concentrated

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.

N R2R2 R1R1 R3R3

CLASSIFICATIONS

PRIMARY R – NH 2 An amine having one alkyl or aromatic group bonded to nitrogen.

EXAMPLES CH 3 – NH 2 methylamine CH 3 – CH 2 – NH 2 ethylamine

SECONDARY R 2 – NH An amine having two alkyl or aromatic groups bonded to nitrogen.

EXAMPLES CH 3 – NH – CH 3 dimethylamine CH 3 – CH 2 – NH – CH 3 ethylmethylamine

TERTIARY R 3 – N An amine having three alkyl or aromatic groups bonded to nitrogen.

EXAMPLES CH 3 – N – CH 3 CH 3 trimethylamine CH 3 – CH 2 – N – CH 3 CH 3 ethyldimethylamine

PREPARATION

WATER HEMLOCK

H│NH│N CH 2 – CH 2 – CH 3 CONIINE Extremely toxic ALKALOID

OPIUM POPPY

O N CH 3 OH MORPHINE Painkillers with strong hallucinogenic & addictive side effects CH 3 │ N O ║ COCH 2 CH 3 DEMEROL Painkillers similar structure to morphine but less side effects

COCA

NCH 3 O ║ COCH 3 O ║ O ─ C ─ COCAINE

CACTUS

CH 2 – CH 2 – NH 2 OCH 3 CH 3 O OCH 3 MESCALINE

DART FROG

H3CH3C H2CH2C HO O H O NCH 3 H CH 3 O C ═ O H3CH3C CH 3 NH BATRACHOTOXIN Derived from D’ word BATRACHOS greek means FROG

GALAPAGOS

GUANIDINE H 2 N – C – NH 2 NH ║ Guano deposits on GALAPAGOS Islands. GUANIDINE is the compound by which migratory bird excrete waste Metabolic nitrogen.

USES

NN CH 2 – CH 2 – NH 2 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 OCH 2 – CH 2 – N CH 3 diphenhydramine(BENADRYL)

C – CH 2 – NH – CH 3 OH HO H EPINEPHRINE

Phenylpropanolamine CH – CH – NH 2 OHCH 3

NH SO 2 SACCHARIN Artificial sweeteners 100 times sweeter than table sugar

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

 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.

EXAMPLES CH 3 – NH 2 methylamine CH 3 – CH 2 – NH 2 COMMON IUPAC methanamine ethylamine COMMON IUPAC ethanamine

EXAMPLES CH 3 – NH – CH 3 dimethylamine CH 3 – CH 2 – NH – CH 3 ethylmethylamine CH 3 – CH 2 – N – CH 3 3 HC ethyldimethylamine CH 3 – N – CH 3 CH 3 trimethylamine

EXAMPLES NH 2 cyclopentanamine NH 2 CH 3 2 – methyl – cyclopentanamine NH 2 Cl 2,4,6 – trichloro – cyclohexanamine

EXAMPLES CH 3 – C ═ CH – CH – CH 3 NH 2 CH 3 4 – methyl – 3 – penten – 2 - amine CH 3 – C ═ CH – CH – C ≡ CH CH 3 – CH 2 NH 2 5 – methyl – 4 – hepten – 1– yne – 3 - amine

 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 –.

EXAMPLES NH – CH 2 – CH 3 N – ethyl – cyclobutanamine NH – (CH 2 ) 5 – CH 3 CH 2 – CH 3 CH 3 – (CH 2 ) 3 3 HC N – hexyl –3 – butyl – 6 – ethyl – 4 – methyl – cyclooctanamine

CH 3 – CH 2 – CH – CH 2 – CH 3 EXAMPLES CH 3 – CH 2 – N – (CH 2 ) 3 – CH 3 N – butyl – N – ethyl – 3 – pentanamine CH 3 – CH 2 – N – (CH 2 ) 7 – CH 3 CH 3 N – ethyl – N – methyl – octanamine

 AMINE AS SUBSTITUENT  NH 2 – 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.

CH 3 – CH 2 – CH – CH 2 – CH 3 EXAMPLES NH 2 3 – aminopentane CH 2 – CH 2 – CH 2 NH 2 OH 3 – amino – 1 – propanol CH 2 – CH 2 – CH 2 NH 2 1,3 – diaminopropane

EXAMPLES NH 2 HO 3 – aminocyclohexanol CH 3 – CH – CH – CH 2 – CH 2 – OH NH 2 CH 2 – CH 2 – CH 3 3 – amino – 4 – methyheptanol

 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.

EXAMPLES NH 2 aniline NH – CH 3 N - methylaniline NH – CH 3 N – methy – 3 – ethyllaniline CH 2 – CH 3

PHYSICAL PROPERTIES

 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.

CHEMICAL PROPERTIES

AMINE + Water ↔ Alkyl ammonium ion + Hydroxide ion CH 3 – NH 2 + H – OHCH 3 – NH OH ־

EXAMPLES NH 2 aniline + H – OH NH 3+ Anilinium ion + OH ־ CH 3 – NH – CH 3 + H – OH dimethylamine CH 3 – NH 2 + – CH 3 + OH ־

AMINE + Acid --- → Amine salt CH 3 – NH 2 + H – ClCH 3 – NH 3+ Cl ־

EXAMPLE CH 3 – CH 2 – NH 2 + CH 3 COO – H CH 3 – CH 2 – NH 3+ CH 3 COO ־

EXAMPLE CH 3 – (CH 2 ) 5 – NH 2 + C 6 H 5 COO – H CH 3 – (CH 2 ) 5 – NH 3+ C 6 H 5 COO ־

AMIDES