Ecgonine-obtained from the leaves of Erythroxylum coca Lam.

D. Ecgonine


Biological Source It is also obtained from the leaves of Erythroxylum coca Lam. (Erythroxylaceae) (Coca) as its l-form.
Chemical Structure

Ecgonine
[1R-(exo, exo)]-3-Hydroxy-8-methyl-8-azabicyclol [3, 2, 1] octane-2-carboxylic acid; (C9H15NO3). It is the principal part of the cocaine molecule.
Isolation Ecgonine may be obtained by the hydrolysis of cocaine as given below:
Cocaine -------Hydrolysis----à  Ecgonine + Benzoic acid + Methanol
Characteristic Features
1. The l-form ecgonine monohydrate is obtained as triboluminescent, monoclinic prisms from ethanol having mp 198°C (anhydrous substance gets decomposed at 205°C).
2. Its specific optical rotation [α ]D15  -450 (C = 5); dissociation constants are: pKa 11.11, and pKb 11.22.
3. Solubility Profile: 1 g dissolves in 5 ml water, 67 ml ethanol, 20 ml ethanol, 75 ml ethyl acetate; sparingly soluble in ether, acetone, benzene, chloroform and petroleum ether.
Identification Tests

1. Ecgonine Hydrochloride (C9H15NO3.HCl): It is obtained as the triclinic plates obtained from water having mp 246°C; [α]D15 -590 (C = 10); soluble in water and slightly in ethanol.
2. dl-Ecgonine Trihydrate: It is obtained as plates from 90% ethanol having mp 93-118°C (anhydrous substance gets decomposed at 212°C).
Uses It is mostly used as a topical anaesthetic.

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