Methylecgonine cinnamate

Methylecgonine cinnamate

Names
IUPAC names methyl (1R,2R,3S,5S)-8-methyl-3-[(E)-3-phenylprop-2-enoyl]oxy-8- azabicyclo[3.2.1]octane-2-carboxylate
Other names Cinnamoylcocaine Cinnamylcocaine
Identifiers
CAS Number	521-67-5
ChemSpider	16735745
Jmol interactive 3D	Image
PubChem	6440936
UNII	O3I44O988U
InChI InChI=1S/C19H23NO4/c1-20-14-9-10-15(20)18(19(22)23-2)16(12-14)24-17(21)11-8-13-6-4-3-5-7-13/h3-8,11,14-16,18H,9-10,12H2,1-2H3/b11-8+/t14?,15?,16?,18-/m1/s1 Key: MQIXMJWNEKUAOZ-GKMMPQBVSA-N InChI=1/C19H23NO4/c1-20-14-9-10-15(20)18(19(22)23-2)16(12-14)24-17(21)11-8-13-6-4-3-5-7-13/h3-8,11,14-16,18H,9-10,12H2,1-2H3/b11-8+/t14?,15?,16?,18-/m1/s1 Key: MQIXMJWNEKUAOZ-GKMMPQBVBP
SMILES CN3C2CCC3CC(OC(=O)/C=C/c1ccccc1)[C@@H]2C(=O)OC
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 said to be 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.^[2]

See also

• Coca alkaloids
• Cocaethylene

External links

• Isolation of cis-Cinnamoylcocaine from Crude Illicit Cocaine via Alumina Column Chromatography D.E.A. Microgram Vol 4 Number 14.
• "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. 2015. doi:10.1007/s00414-014-1061-6.

References

1. "Cocaine and Cinnamoylcocaine Content of Erythroxylum Species". Annals of Botany 51 (5): 641–659.
2. Merck Chemical Index, 1985
3. "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.". J Forensic Sci 52: 860–6. Jul 2007. doi:10.1111/j.1556-4029.2007.00476.x. PMID 17553089.