Cinnamoylcocaine

Title: Cinnamoylcocaine
CAS Registry Number: 521-67-5
CAS Name: [1R-(exo,exo)]-8-Methyl-3-[(1-oxo-3-phenyl-2-propenyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester
Additional Names: ecgonine cinnamate methyl ester; cinnamoylecgonine methyl ester; cinnamylcocaine; cinnamoylmethylecgonine
Molecular Formula: C19H23NO4
Molecular Weight: 329.39
Percent Composition: C 69.28%, H 7.04%, N 4.25%, O 19.43%
Literature 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).
Properties: Needles, mp 121°. [a]D -4.7° (chloroform). Almost insol in water; sol in alcohol, chloroform, ether.
Melting point: mp 121°
Optical Rotation: [a]D -4.7° (chloroform)
Status: This monograph has been retired and is no longer subject to revision or update.
Cinnamyl Alcohol Cinnamyl Anthranilate Cinnamyl Cinnamate Cinnoline Cinobufotalin

Methylecgonine cinnamate
Cinnamoylcocaine.svg
Identifiers
CAS number 521-67-5 YesY
PubChem 6440936
ChemSpider 16735745 YesY
Jmol-3D images Image 1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is said to be pharmacologically inactive.[1] But some studies funded by anti-drug agencies imply that it is active when smoked.[citation needed] Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline.[2]