Methylvanillylecgonine
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| Names | |
|---|---|
| IUPAC name
Methyl 3β-[(3-hydroxy-4-methoxybenzoyl)oxy]tropane-2β-carboxylate | |
| Systematic IUPAC name
Methyl (1R,2R,3S,5S)-3-[(3-hydroxy-4-methoxybenzoyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | |
| Other names
Hydroxymethoxycocaine 4′-hydroxy-3′-methoxycocaine parahydroxymetamethoxycocaine | |
| Identifiers | |
3D model (JSmol) |
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| Properties | |
| C18H23NO6 | |
| Molar mass | 349.383 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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Methylvanillylecgonine or vanillylmethylecgonine is a cocaine analog and metabolite of cocaine found in human urine (possibly with co-ingestion of vanillin-vanilla containing products, as a result of cleavage and binding in vivo but more probably the result of the same metabolic pathways by which vanillylmandelic acid is formed).[1][2][3]
See also
[edit]References
[edit]- ↑ Smith, R. Martin; Poquette, Michael A.; Smith, Paula J. (1984). "Hydroxymethoxybenzoylmethylecgonines: New metabolites of cocaine from human urine". Journal of Analytical Toxicology. 8 (1): 29–34. doi:10.1093/jat/8.1.29. PMID 6708474.
- ↑ Smith, Michael L.; Shimomura, Eric; Paul, Buddha D.; Cone, Edward J.; Darwin, W. David; Huestis, Marilyn A. (March 2010). "Urinary excretion of ecgonine and five other cocaine metabolites following controlled oral, intravenous, intranasal, and smoked administration of cocaine". Journal of Analytical Toxicology. 34 (2): 57–63. doi:10.1093/jat/34.2.57. ISSN 1945-2403. PMC 3159558. PMID 20223096.
- ↑ Ramcharitar, V.; Levine, B.; Smialek, JE (1995). Benzoylecgonine and Ecgonine Methyl Ester Concentrations in Urine Specimens. ASTM International.
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