Cinnamyl cocaine

Ecgonine like tropine does not occur as such in plants. The partially hydrolyzed cocaine, viz., the benzoyl ecgonine, is a natural plant alkaloid. An ester analogous to cocaine with the radical of cinnamic acid, CeHs—CH = CH—COOH, in place of that of benzoic acid, is a natural alkaloid in Java coca leaves and is known as cinnamyl cocaine. 

Much of the cocaine used in this country is prepared from the crude alkaloid which is manufactured in the countries where the plant grows. The alkaloids are extracted from the leaves by kerosene or some other cheap immiscible solvent in the presence of an alkali, the alkaloids being separated from the solvent with dilute sulphuric acid from which cocaine is precipitated by sodium carbonate. This crude substance represents about 90 per cent, of cocaine. A good deal of cocaine is manufactured in Germany from the Java coca leaves which contain chiefly cinnamyl cocaine. This alkaloid is hydrolized by boiling with diluted hydrochloric acid and the ecgonine so obtained treated with benzoic anhydride and methyl iodide. The other coca bases may also be converted into cocaine by a similar process as suggested by Liebermann (B. Chem. G., 1888, xxi, 3196). 

The ash from 0.5 Gm. is negligible. Dissolve 0.1 Gm. of finely powdered Cocaine in 1 cc. of sulphuric acid not more than a slightly yellow tint is produced (readily carbonizable substances). Dissolve 0.3 Gm. of finely powdered Cocaine in 1 cc. of normal hydrochloric acid, gently warming, if necessary, to aid solution, and dilute with distilled water to 15 cc. 5 cc. portions of this solution do not respond to the tests for cinnamyl-cocaine and for isoatropyl-cocaine under Cocaince Hydrochloridum. ... 

When pseudopelletierine is reduced and acylated, the resulting esters are less potent than cocaine. For example, benzoyl-A-methylgranatoline (VI), cinnamyl-A-methylgranatoline (VII), andp-aminobenzoyl-A-methyl-granatoline (VIII), have been prepared (14). Compound VI showed the highest anesthetic potency and VIII the lowest. In guinea pigs the relative... 

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