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]
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| Names | |
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| IUPAC name
methyl (1R,2R,3S,5S)-8-methyl-3-[(E)-3-phenylprop-2-enoyl]oxy-8- | |
| Other names
Cinnamoylcocaine | |
| Identifiers | |
 Y | |
3D model (JSmol) |
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| ChemSpider |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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). | |
