Methylecgonine cinnamate

Methylecgonine cinnamate

Names
IUPAC name 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	50763-20-7^Y 521-67-5 (non-specific)^Y
3D model (JSmol)	Interactive image
ChemSpider	16735745^Y
PubChem CID	6440936
UNII	O3I44O988U^Y
CompTox Dashboard (EPA)	DTXSID701334867 DTXSID60893899, DTXSID701334867
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^Y Key: MQIXMJWNEKUAOZ-GKMMPQBVSA-N^Y 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
Properties
Chemical formula	C19H23NO4
Molar mass	329.396 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) 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 pharmacologically inactive,^[2] but some studies funded by anti-drug agencies imply that it is active when smoked.^{[citation needed]} 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] Methylecgonine cinnamate is mentioned in patents of active cocaine analogue structures.^[4][5]

See also

• Coca alkaloids
• Cocaethylene
• Salicylmethylecgonine

References

1. Plowman, T.; Rivier, L. (1983). "Cocaine and Cinnamoylcocaine Content of Erythroxylum Species". Annals of Botany. 51 (5): 641–659. doi:10.1093/oxfordjournals.aob.a086511.
2. Merck Chemical Index, 1985
3. Casale, J. F.; Hays, P. A.; Toske, S. G.; Berrier, A. L. (Jul 2007). "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 (4): 860–6. doi:10.1111/j.1556-4029.2007.00476.x. PMID 17553089. S2CID 43863333.
4. U.S. patent 6,479,509 Patent inventor Frank Ivy Carroll, Assignee: Research Triangle Institute
5. 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.
• Rubio, Nelida Cristina; Hastedt, Martin; Gonzalez, Jorge; Pragst, Fritz (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. doi:10.1007/s00414-014-1061-6. PMID 25138383. S2CID 20712368.