Amines + Amides Flashcards
Characteristics Amines?
Derived from Ammonia –> 1 or more Hydrogen replaced by a C Chain ( Alkyl substitution )
Primary/Secondary/Tertiary Amine
Quaternary Amine –> Ammonium Salt
Preparation of Amines ?
Ammonia + Alkyl Halide
Nucleophilic attack on the Carbon atom by Ammonia
Reactions of Primary Amines?
- Salt formation –> act as bases
- Amide formation –> Acylation (RCO) –> ALK + 1. Amine
- Elimination of Ammonia –> Non oxidative Deamination
- Reactions with Nitrous acid
With 1. Aliphatic amines –> + Heat = Alkohol+ N2
With 1. Aromatic amines –> + Phenols = Diazonium Salts –> AZO Dyes
Reactions of Secondary Amines ?
+ Nitrous acid –> Nitrosamines (yellow)
Nitrosamines
Food preservative with Nitrites
Animal carcinogen
Important derivatives ?
Ethanolamine Choline Acetylcholine Succinylcholine Aniline Benzidine
Ethanolamine?
Colamine
Constituent of Phospholipids
Choline?
Quaternary ammonium ion
Important for biological Processes
Component of Lecithins –> must be supplied by Diet
Acetylcholine?
Acetic acid ester of Choline
Liberated at junctions btw. nerve cells –> Receptor
ACh Receptor –> Target of deadly known Neurotoxins
Achetylcholinesterase?
Degradation of ACh Molecule before new Potential arrives
–> Serine Esterase
Serine Esterase
Irreversably inhibited by toxic esters of Phosphoric acid
Block the alkcohol group of serine in the active center
(Organophosphates)
Insecticides?
Parathion
Tabun / Sarin ?
Military nerve gases
Succinylcholine Medicine
Muscle relaxant during surgery
How does Succinylcholine operate?
It is slowly hydrolyzed –> Leads to Depolarization
Persistent but reversible!
Aniline
Colourless liquid Aromatic odour Intermediate in Dyestuff Production Manufacture of Pharmaceuticals Shoe polish Resins
Aniline Reactions
With acids –> Ammonium Salt (Aniline Hydrochloride)
Aniline Medicine
Manufacture of Pharmaceuticals
Absorbed through skin
1. Operates with acetic acid to Amide acetanilide –> Urine
2. Oxidation to Phenylhydroxyamine and Nitrobenzene
Benzidine
White, crystalline Powder
Intermediate for the synthesis of dyes for cotton
Benzidine blue –> Test for Peroxidases
Carcinogen –> Rarely used
What are Peroxidases ?
Substances cleaving Hydrogen Peroxide
Peroxidases can contain a heme cofactor in their active sites
Peroxidasen sind Enzyme, welche die Reduktion von Peroxiden (meist Wasserstoffperoxid) katalysieren
Biologically active amines
Derivatives of amino acids
Involve Neurotransmitters and Hormones
Inactivation –> oxidative deamination
Influence the CNS
Phenylethylamine Ephedrine Mescaline Amphetamine Phenmetrazine
What are the decarboxylated products of Tyrosine/ Tryptophane/ Histidine
Dopamin and Catecholamine Derivatives
–> Serotonin + Histamine
Phenethylamine
Parent substance of sympathomimetic amines
Effect of sympathomimetica
They mimic or interfere with the functioning of the sympathetic nervous system by affecting the release or action of norepinephrine and epinephrine
