Cinnamoyl Cocaine-Synonyms Ecgonine Methyl Ester; Cinnamoylcocaine; Cinnamoyl-methylecgonine; Ecgonine Cinnamate

C. Cinnamoyl Cocaine

Synonyms Ecgonine Methyl Ester; Cinnamoylcocaine; Cinnamoyl-methylecgonine; Ecgonine Cinnamate Methyl Ester.

Biological Source It is obtained from the leaves of Erythroxylon coca Lann. (Erythroxylaceae), particularly from the Javanese leaves.

Chemical Structure

[1R-(exo, exo)]-8-Methyl-3-[(1-oxo-3-phenyl-2-propenyl)oxy]-8-azabicyclol [3, 2, 1] octane-2-carboxylic acid methyl ester; (C₁₉H₂₃NO₄).

Isolation Instead of the Peruvian leaves the Java leaves of E. coca are treated in the same manner and fashion as described under cocaine earlier (section ‘B’). It has been observed that the mixed hydrochlorides mostly comprise of cinnamoyl cocaine which gets separated as fine needles.

Characteristic Features

1. It is obtained as fine needles having mp 121°C.

2. Its specific optical rotation is [α]_D – 4.7° (chloroform).

3. It is freely soluble in ether, ethanol and chloroform; and almost insoluble in water.

Identification Tests

1. It reduces an acidic solution of KMnO₄ in cold i.e., at ambient temperature, which helps to detect the presence of this alkaloid in an admixture with cocaine.

2. It undergoes hydrolysis when warmed with HCl to yield l-ecgonine, cinnamic acid and methanol.
Source:Pharmacognosy And Pharmacobiotechnology By Ashutosh Kar