Methylvanillylecgonine

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]

Methylvanillylecgonine
Names
Preferred 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
CAS Number
3D model (JSmol)
InChI
  • InChI=1S/C18H23NO6/c1-19-11-5-6-12(19)16(18(22)24-3)15(9-11)25-17(21)10-4-7-13(20)14(8-10)23-2/h4,7-8,11-12,15-16,20H,5-6,9H2,1-3H3
    Key: BHHXESNMOOYSOJ-UHFFFAOYSA-N
SMILES
  • COc(c1)c(O)ccc1C(=O)OC2CC(CC3)N(C)C3C2C(=O)OC
Properties
Chemical formula
 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).
Infobox references

See also

References
  1. 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.


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