Norhydrocodone - Misplaced Pages

Chemical compound Pharmaceutical compound

Norhydrocodone
Clinical data

Other names	(5α)-3-Methoxy-4,5-epoxymorphinan-6-one
Dependence liability	High
Identifiers
IUPAC name (4R,4aR,7aR,12bS)-9-Methoxy-2,3,4,4a,5,6,7a,13-octahydro-1H-4,12-methanobenzofuroisoquinoline-7-one
CAS Number	5083-62-5
PubChem CID	13001738
ChemSpider	32698944
UNII	18NB5F1JT4
CompTox Dashboard (EPA)	DTXSID70198862
Chemical and physical data
Formula	C₁₇H₁₉NO₃
Molar mass	285.343 g·mol
3D model (JSmol)	Interactive image
SMILES COC1=C2C3=C(C453(CCN4)(O2)C(=O)CC5)C=C1
InChI InChI=1S/C17H19NO3/c1-20-13-5-2-9-8-11-10-3-4-12(19)16-17(10,6-7-18-11)14(9)15(13)21-16/h2,5,10-11,16,18H,3-4,6-8H2,1H3/t10-,11+,16-,17-/m0/s1 Key:JGORUXKMRLIJSV-YNHQPCIGSA-N

Norhydrocodone is the major metabolite of the opioid analgesic hydrocodone. It is formed from hydrocodone in the liver via N-demethylation predominantly by CYP3A4. Unlike hydromorphone, a minor metabolite of hydrocodone, norhydrocodone is described as inactive. However, norhydrocodone is actually an agonist of the μ-opioid receptor with similar potency to hydrocodone, but has been found to produce only minimal analgesia when administered peripherally to animals. This is likely due to poor blood-brain-barrier and thus central nervous system penetration.

References

^ Zhou S (6 April 2016). Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism. CRC Press. pp. 164–. ISBN 978-1-4665-9788-4.
Dasgupta A, Langman LJ (23 April 2012). Pharmacogenomics of Alcohol and Drugs of Abuse. CRC Press. pp. 175–. ISBN 978-1-4398-5611-6.
^ Navani DM, Yoburn BC (November 2013). "In vivo activity of norhydrocodone: an active metabolite of hydrocodone". The Journal of Pharmacology and Experimental Therapeutics. 347 (2): 497–505. doi:10.1124/jpet.113.207548. PMID 23995596. S2CID 31072872.