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 checkY
  • 521-67-5 (non-specific) checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 16735745 checkY
PubChem CID
  • 6440936
UNII
  • O3I44O988U checkY
CompTox Dashboard (EPA)
  • DTXSID60893899 Edit this at Wikidata
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 checkY
    Key: MQIXMJWNEKUAOZ-GKMMPQBVSA-N checkY
  • 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
  • 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).
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Infobox references
Chemical compound

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] 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. ^ 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. ^ a b 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.