Chemistry:Norhydrocodone

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Short description: Chemical compound
Norhydrocodone
Norhydrocodone.svg
Clinical data
Other names(5α)-3-Methoxy-4,5-epoxymorphinan-6-one
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC17H19NO3
Molar mass285.343 g·mol−1
3D model (JSmol)

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]

See also

References

  1. 1.0 1.1 Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism. CRC Press. 6 April 2016. pp. 164–. ISBN 978-1-4665-9788-4. https://books.google.com/books?id=UJqmCwAAQBAJ&pg=PA164. 
  2. Pharmacogenomics of Alcohol and Drugs of Abuse. CRC Press. 23 April 2012. pp. 175–. ISBN 978-1-4398-5611-6. https://books.google.com/books?id=AiHaRjs3grYC&pg=PA175. 
  3. 3.0 3.1 "In vivo activity of norhydrocodone: an active metabolite of hydrocodone". The Journal of Pharmacology and Experimental Therapeutics 347 (2): 497–505. November 2013. doi:10.1124/jpet.113.207548. PMID 23995596.