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
3D model (JSmol)
ChemSpider
UNII
  • 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
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

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.[2] It is notable that methylecgonine cinnamate is given in patents of active cocaine analogue structures.[4][5]

See also

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. 1 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.
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