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VIBRO CHOLERAE. PUTRESCINE. H 2 N – CH 2 – CH 2 – CH 2 – CH 2 – NH 2. (1,4-diaminobutane or butanediamine ). CADAVERINE. H 2 N – CH 2 – CH 2 – CH 2 – CH 2 – CH 2 – NH 2. (1,5-diaminopentane or pentanediamine ). CHOLERA BACTERIUM. PUTRESCINE & CADAVERINE.
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PUTRESCINE H2N – CH2 – CH2 – CH2 – CH2 – NH2 (1,4-diaminobutane or butanediamine) CADAVERINE H2N – CH2 – CH2 – CH2 – CH2 – CH2 – NH2 (1,5-diaminopentane or pentanediamine) CHOLERA BACTERIUM
PUTRESCINE & CADAVERINE • 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.
SPERMINE H2N – (CH2)4 – NH – (CH2)3 – NH2 SPERMIDINE H2N – (CH2)3 – NH – (CH2)4 – NH – (CH2)3 – NH2 First isolated from human seminal fluid, were they are highly concentrated
MELAMINE 1,3,5-triazine-2,4,6-triamine
AMINES • 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 substituentssuch 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 R3 R1 R2
PRIMARY R – NH2 An amine having one alkyl or aromatic group bonded to nitrogen.
EXAMPLES CH3 – NH2 methylamine CH3 – CH2 – NH2 ethylamine
SECONDARY R2 – NH An amine having two alkyl or aromatic groups bonded to nitrogen.
EXAMPLES CH3–NH – CH3 dimethylamine CH3 – CH2–NH – CH3 ethylmethylamine
TERTIARY R3 – N An amine having three alkyl or aromatic groups bonded to nitrogen.
EXAMPLES CH3–N – CH3 trimethylamine CH3 CH3 CH3 – CH2–N – CH3 ethyldimethylamine
CONIINE H │ N CH2 – CH2 – CH3 Extremely toxic ALKALOID
CH3 │ N CH3 MORPHINE N O ║ COCH2CH3 DEMEROL O OH Painkillers with strong hallucinogenic & addictive side effects Painkillers similar structure to morphine but less side effects
N CH3 O ║ COCH3 O ║ O ─ C ─ COCAINE
CH2 – CH2 – NH2 CH3O OCH3 OCH3 MESCALINE
BATRACHOTOXIN CH3 H O CH3 H2C HO C═ O H3C O O NCH3 H3C NH HO H Derived from D’ word BATRACHOS greek means FROG
GUANIDINE NH ║ H2N – C – NH2 Guano deposits on GALAPAGOS Islands. GUANIDINE is the compound by which migratory bird excrete waste Metabolic nitrogen.
HISTAMINE CH2 – CH2 – NH2 N N H 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…..
(BENADRYL) diphenhydramine CH3 O CH2 – CH2 – N CH3 CH
EPINEPHRINE OH C – CH2 – NH – CH3 HO H HO
Phenylpropanolamine CH – CH – NH2 OH CH3
SACCHARIN NH SO2 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
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.
EXAMPLES CH3 – NH2 IUPAC methanamine COMMON methylamine CH3 – CH2 – NH2 IUPAC ethanamine COMMON ethylamine
EXAMPLES CH3–NH – CH3 dimethylamine ethylmethylamine CH3 – CH2–NH – CH3 3HC CH3–N – CH3 CH3 – CH2–N – CH3 CH3 ethyldimethylamine trimethylamine
EXAMPLES NH2 NH2 CH3 cyclopentanamine 2 – methyl – cyclopentanamine Cl 2,4,6 – trichloro – cyclohexanamine NH2 Cl Cl
EXAMPLES CH3 NH2 CH3– C ═ CH – CH – CH3 4 – methyl – 3 – penten – 2 - amine CH3– C ═ CH – CH – C ≡ CH CH3 – CH2 NH2 5 – 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 – .
EXAMPLES NH – CH2 – CH3 N – ethyl – cyclobutanamine CH2 – CH3 3HC CH3 – (CH2)3 NH – (CH2)5 – CH3 N – hexyl –3 – butyl – 6 – ethyl – 4 – methyl – cyclooctanamine