13-02324. Cinnamoylcocaine [Archived]

Nomenclature

CAS number: 521-67-5
[1R-(exo,exo)]-8-Methyl-3-[(1-oxo-3-phenyl-2-propenyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester; ecgonine cinnamate methyl ester; cinnamoylecgonine methyl ester; cinnamylcocaine; cinnamoylmethylecgonine.
C19H23NO4; mol wt 329.39.
C 69.28%, H 7.04%, N 4.25%, O 19.43%.

Description and references

From leaves of Erythroxylon coca Lam., Erythroxylaceae, particularly from the Javanese leaves: Liebermann, Ber. 22, 2661 (1889); de Jong, Rec. Trav. Chim. 67, 484 (1948); Hegnauer, Fikenscher, Pharm. Acta Helv. 35, 43 (1960); from E. monogynum Roxb.: Chopra, Gosh, Arch. Pharm. 276, 340 (1938).

Chemical structure

Properties

Needles, mp 121°. [α]D 4.7° (chloroform). Almost insol in water; sol in alcohol, chloroform, ether.

Status

This monograph has been retired and is no longer subject to revision or update.