Methylecgonine cinnamate is a natural
tropane
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) ...
alkaloid
Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids.
Alkaloids are produced by a large varie ...
found within the
coca
Coca is any of the four cultivated plants in the family Erythroxylaceae, native to western South America. Coca is known worldwide for its psychoactive alkaloid, cocaine. Coca leaves contain cocaine which acts as a mild stimulant when chewed or ...
plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to
cocaine
Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...
. It is pharmacologically inactive,
[Merck Chemical Index, 1985] 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. Methylecgonine cinnamate can dimerize to the
truxillic acid derivative
In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
truxilline.
Methylecgonine cinnamate is mentioned in patents of active cocaine analogue structures.
U.S. patent US6479509 B1 structures given for submission, 5th compound down in image.
/ref>
See also
* Coca alkaloid
Coca alkaloids are the alkaloids found in the coca plant, ''Erythroxylum coca''.Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop. Emanuel L. Johnson and Stephen D. Emche, Ann. Bot., 1994, volume 73, issue 6, pag ...
s
* Cocaethylene
Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver in small amounts when cocaine and ethanol coexi ...
* Salicylmethylecgonine
References
External links
Isolation of ''cis''-Cinnamoylcocaine from Crude Illicit Cocaine via Alumina Column Chromatography
D.E.A. Microgram Vol 4 Number 14.
*{{cite journal , year = 2015 , title = Possibilities for discrimination between chewing of coca leaves and abuse of cocaine by hair analysis including hygrine, cuscohygrine, cinnamoylcocaine and cocaine metabolite/cocaine ratios , journal = International Journal of Legal Medicine , volume = 129 , issue = 1, pages = 69–84 , doi=10.1007/s00414-014-1061-6, pmid = 25138383 , last1 = Rubio , first1 = Nelida Cristina , last2 = Hastedt , first2 = Martin , last3 = Gonzalez , first3 = Jorge , last4 = Pragst , first4 = Fritz , s2cid = 20712368
Tropane alkaloids found in Erythroxylum coca
Cinnamate esters
Methyl esters