3-Methoxymorphinan

3-Methoxymorphinan is a levomethorphan metabolite that has been shown to produce local anesthetic effects.[1] It is the CYP3A4 metabolite of dextromethorphan,[2] and is itself metabolized by the liver enzyme CYP2D6.[3]

Not to be confused with Dextrorphan, Dextromethorphan, or Levomethorphan.
3-Methoxymorphinan
Legal status
Legal status
  • US: uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.014.764
Chemical and physical data
FormulaC17H23NO
Molar mass257.377 g·mol−1
InChI
  • 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 Y
  • Key:ILNSWVUXAPSPEH-USXIJHARSA-N Y
 NY (what is this?)  (verify)

See also

References
  1. Hou, Chia-Hui; Tzeng, Jann-Inn; Chen, Yu-Wen; Lin, Ching-Nan; Lin, Mao-Tsun; Tu, Chieh-Hsien; Wang, Jhi-Joung (2006). "Dextromethorphan, 3-methoxymorphinan, and dextrorphan have local anaesthetic effect on sciatic nerve blockade in rats". European Journal of Pharmacology. 544 (1–3): 10–6. doi:10.1016/j.ejphar.2006.06.013. PMID 16844109.
  2. Min, David I.; Ku, Yi-Min; Vichiendilokkul, Aungkana; Fleckenstein, Lawrence L. (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): 753–9. doi:10.1592/phco.19.9.753.31536. PMID 10391422.
  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): 1928–35. doi:10.1016/j.fct.2009.05.004. PMID 19445995.


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