3-Methoxymorphinan
Chemical compound
- US: uncontrolled
- 1531-25-5 N
- 5484286
- 10207434 Y
- 497WV2EY4T
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
3-Methoxymorphinan is an inactive metabolite of both dextromethorphan and levomethorphan, and has been shown to produce local anesthetic effects.[1] It is the CYP3A4 metabolite of the aforementioned drugs,[2] and is itself metabolized by the liver enzyme CYP2D6.[3]
See also
- 3-hydroxymorphinan
- Dextrorphan
- Dextromethorphan
- Levomethorphan
- Morphinan
References
- ^ 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.
- ^ 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.
- ^ 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.
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