Page 70 - phytochemistry general program

Cinnamyl cocaine .2
It occurs in Java coca leaves in a percentage higher than that of cocaine as

rosettes or needles, m.p.121 oC, insoluble in water, soluble in organic solvents.
The platinic chloride of cinnamyl cocaine is amorphous (c.f. cocaine). When

heated with hydrochloric acid, cinnamyl cocaine yields ecgonine, cinnamic acid
.and methyl alcohol. It reduces acid potassium permanganate solution on cold

Truxillines .3
They are esters of methyl ecgonine with α or β-truxillic acid. Truxillic acids

are dimers of cinnamic acid. Solutions of the base are laevorotatory.

Cocaine

Me COOMe
NH

O

HO

It is benzoylecgonine methyl ester. It occurs as laevorotatory colorless
prisms (m.p. 96-98 oC) with a bitter taste followed by numbness; It is slightly
volatile, sparingly soluble in water, soluble in alcohol, ether, chloroform, petroleum
ether and benzene. Partial hydrolysis is affected by boiling with water to give
methanol and benzoyl ecgonine, while complete hydrolysis by alkali, or when
heated with dil.hydrochloric acid at 160 oC, yield ecgonine, benzoic acid and

methanol.

hydrolysis
Cocaine ⎯⎯⎯⎯→ ecgonine + benzoic acid + methanol

Cocaine HCl
It is the official salt in B.P. 2008 and E.P. 84.
Cocaine HCl is readily soluble in water (1:0.5), alcohol, chloroform (1:15) but

insoluble in ether or petroleum ether.
Uses of cocaine

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