norhydrocodone

{{Short description|Chemical compound}}

{{Drugbox

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| 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

| image = Norhydrocodone.svg

| width = 200px

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| dependency_liability = High

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| CAS_number_Ref =

| CAS_number = 5083-62-5

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| PubChem = 13001738

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| ChemSpiderID = 32698944

| UNII = 18NB5F1JT4

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| C = 17

| H = 19

| N = 1

| O = 3

| smiles = COC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](O2)C(=O)CC5)C=C1

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = JGORUXKMRLIJSV-YNHQPCIGSA-N

| synonyms = (5α)-3-Methoxy-4,5-epoxymorphinan-6-one

}}

Norhydrocodone is the major metabolite of the opioid analgesic hydrocodone.{{cite book| vauthors = Zhou S |title=Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism|url=https://books.google.com/books?id=UJqmCwAAQBAJ&pg=PA164|date=6 April 2016|publisher=CRC Press|isbn=978-1-4665-9788-4|pages=164–}} 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.{{cite book| vauthors = Dasgupta A, Langman LJ |title=Pharmacogenomics of Alcohol and Drugs of Abuse|url=https://books.google.com/books?id=AiHaRjs3grYC&pg=PA175|date=23 April 2012|publisher=CRC Press|isbn=978-1-4398-5611-6|pages=175–}} 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.{{cite journal | vauthors = Navani DM, Yoburn BC | s2cid = 31072872 | title = In vivo activity of norhydrocodone: an active metabolite of hydrocodone | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 347 | issue = 2 | pages = 497–505 | date = November 2013 | pmid = 23995596 | doi = 10.1124/jpet.113.207548 }} This is likely due to poor blood-brain-barrier and thus central nervous system penetration.