Back متیل‌اقونین سینامات AZB Cinamato metilecgonina Spanish متیل‌اگونین سینامات Persian Cinnamate de méthylecgonine French シンナモイルコカイン Japanese Metilekgonin cinamat Serbo-Croatian Metilekgonin cinamat Serbian

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
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).
☒N verify (what is checkY☒N ?)

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]

  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.
From Wikipedia, the free encyclopedia · View on Wikipedia

Developed by Nelliwinne