3-Methoxymorphinan

3-Methoxymorphinan
Legal status
Legal status	US: uncontrolled;
Identifiers
CAS Number	1531-25-5 ;
PubChem CID	5484286;
ChemSpider	10207434 ;
UNII	497WV2EY4T;
ECHA InfoCard	100.014.764
Chemical and physical data
Formula	C17H23NO
Molar mass	257.377 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 ; Key:ILNSWVUXAPSPEH-USXIJHARSA-N ;
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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]

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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[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.

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See also

References