Norhydrocodone

Norhydrocodone is the major metabolite of the opioid analgesic hydrocodone.[1] It is formed from hydrocodone in the liver via N-demethylation predominantly by CYP3A4.[1] Unlike hydromorphone, a minor metabolite of hydrocodone, norhydrocodone is described as inactive.[2] 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.[3] This is likely due to poor blood-brain-barrier and thus central nervous system penetration.[3]

Norhydrocodone
Clinical data
Other names(5α)-3-Methoxy-4,5-epoxymorphinan-6-one
Identifiers
IUPAC name
  • (4R,4aR,7aR,12bS)-9-Methoxy-2,3,4,4a,5,6,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H19NO3
Molar mass285.343 g·mol−1
3D model (JSmol)
SMILES
  • COC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](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

See also

References
  1. Zhou S (6 April 2016). Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism. CRC Press. pp. 164–. ISBN 978-1-4665-9788-4.
  2. Dasgupta A, Langman LJ (23 April 2012). Pharmacogenomics of Alcohol and Drugs of Abuse. CRC Press. pp. 175–. ISBN 978-1-4398-5611-6.
  3. 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.
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