Methylecgonine cinnamate explained

Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant.^[1] Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is pharmacologically inactive,^[2] but some studies funded by anti-drug agencies imply that it is active when smoked. Furthermore, the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing agencies to postulate that illicit manufacturers have changed their oxidation procedures when refining cocaine from a crude form.^[3] Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline. It is notable that methylecgonine cinnamate is given in patents of active cocaine analogue structures.^{[4] [5]}

See also

• Coca alkaloids
• Cocaethylene
• Salicylmethylecgonine

References

1. 10.1093/oxfordjournals.aob.a086511 . Cocaine and Cinnamoylcocaine Content of Erythroxylum Species . Annals of Botany . 51 . 5 . 641–659 . 1983 . Plowman . T. . Rivier . L. .
2. Merck Chemical Index, 1985
3. 17553089 . 10.1111/j.1556-4029.2007.00476.x . 52 . 4 . Four new illicit cocaine impurities from the oxidation of crude cocaine base: formation and characterization of the diastereomeric 2,3-dihydroxy-3-phenylpropionylecgonine methyl esters from cis- and trans-cinnamoylcocaine . Jul 2007 . J Forensic Sci . 860–6. Casale . J. F. . Hays . P. A. . Toske . S. G. . Berrier . A. L. . 43863333 .
4. Patent inventor Frank Ivy Carroll, Assignee: Research Triangle Institute
5. https://patentimages.storage.googleapis.com/US6479509B1/US06479509-20021112-C00016.png U.S. patent US6479509 B1 structures given for submission, 5th compound down in image.

External links

• Isolation of cis-Cinnamoylcocaine from Crude Illicit Cocaine via Alumina Column Chromatography D.E.A. Microgram Vol 4 Number 14.
• 2015 . Possibilities for discrimination between chewing of coca leaves and abuse of cocaine by hair analysis including hygrine, cuscohygrine, cinnamoylcocaine and cocaine metabolite/cocaine ratios . International Journal of Legal Medicine . 129 . 1. 69–84 . 10.1007/s00414-014-1061-6. 25138383 . Rubio . Nelida Cristina . Hastedt . Martin . Gonzalez . Jorge . Pragst . Fritz . 20712368 .