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
521-67-5 YesY
ChemSpider 16735745 YesY
Jmol 3D model Interactive image
PubChem 6440936
UNII O3I44O988U YesY
  • 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 YesY
    Key: MQIXMJWNEKUAOZ-GKMMPQBVSA-N YesY
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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]

See also

External links

References

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  2. 2.0 2.1 Merck Chemical Index, 1985
  3. Lua error in package.lua at line 80: module 'strict' not found.


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