3-Methoxymorphinan

3-Methoxymorphinan
Legal status
Legal status
  • US: uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.014.764 Edit this at Wikidata
Chemical and physical data
FormulaC17H23NO
Molar mass257.377 g·mol−1
  • InChI=1S/C17H23NO/c1-19-13-6-5-12-10-16-14-4-2-3-7-17(14,8-9-18-16)15(12)11-13/h5-6,11,14,16,18H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1 checkY
  • Key:ILNSWVUXAPSPEH-USXIJHARSA-N checkY
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3-Methoxymorphinan is an inactive metabolite of both dextromethorphan and levomethorphan, and has been shown to produce local anesthetic effects. It is the CYP3A4 metabolite of the aforementioned drugs, and is itself metabolized by the liver enzyme CYP2D6.

See also

References

  1. ↑ Hou CH, Tzeng JI, Chen YW, Lin CN, Lin MT, Tu CH, Wang JJ (August 2006). "Dextromethorphan, 3-methoxymorphinan, and dextrorphan have local anaesthetic effect on sciatic nerve blockade in rats". European Journal of Pharmacology. 544 (1–3): 10–16. doi:10.1016/j.ejphar.2006.06.013. PMID 16844109.
  2. ↑ Min DI, Ku YM, Vichiendilokkul A, Fleckenstein LL (June 1999). "A urine metabolic ratio of dextromethorphan and 3-methoxymorphinan as a probe for CYP3A activity and prediction of cyclosporine clearance in healthy volunteers". Pharmacotherapy. 19 (6): 753–759. doi:10.1592/phco.19.9.753.31536. PMID 10391422. S2CID 32243163.
  3. ↑ Strauch K, Lutz U, Bittner N, Lutz WK (August 2009). "Dose-response relationship for the pharmacokinetic interaction of grapefruit juice with dextromethorphan investigated by human urinary metabolite profiles". Food and Chemical Toxicology. 47 (8): 1928–1935. doi:10.1016/j.fct.2009.05.004. PMID 19445995.