Page 74 - Phytochemistry 2 (06-PG 605)
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Ecgonine

                                Me

                    NH
                                                 COOH

                                        OH

                                   H
                           Ecgonine

Ecgonine is tropine 2-carboxylic acid. It contains four

asymmetric carbon atoms consequently a number of optically

active stereoisomeric forms are possible.

Ecgonine is obtained by hydrolysis of cocaine with alkali or

with HCl at 160oC.

                         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.

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