Methylecgonine cinnamate

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Methylecgonine cinnamate
Cinnamoylcocaine.svg
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
3D model (Jmol)
ChemSpider
UNII
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.[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]

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References[edit]

  1. ^ "Cocaine and Cinnamoylcocaine Content of Erythroxylum Species". Annals of Botany. 51 (5): 641–659. 
  2. ^ a b 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. 
  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.