{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 412254473 | IUPAC_name = 3,6α-Dihydroxy-4,5α-epoxy-7,8-didehydromorphinan | image = Normorphine.svg | image_class = skin-invert-image | width = 180 <!--Clinical data-->| tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = S9 | legal_BR = A1 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}</ref> | legal_CA = Schedule I | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = Schedule I | legal_DE = Anlage I | dependency_liability = High | routes_of_administration = <!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = <!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 466-97-7 | ATC_prefix = none | ATC_suffix = | PubChem = 5462508 | DrugBank = | KEGG = C11785 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4575435 | IUPHAR_ligand = 1630 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | UNII_Ref = {{fdacite|changed|FDA}} | UNII = XUI1Y24IMI <!--Chemical data-->| C = 16 | H = 17 | N = 1 | O = 3 | ChEMBL = 1227 | synonyms = Normorphine | smiles = c1cc(c2c3c1C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](O2)[C@H](C=C5)O)O | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = ONBWJWYUHXVEJS-ZTYRTETDSA-N }}
'''Normorphine''' is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s<ref>{{cite journal | vauthors = Clark RL, Pessolano AA, Weijlard J, Pfister K | title = N-Substituted epoxymorphinans | journal = Journal of the American Chemical Society | date = October 1953 | volume = 75 | issue = 20 | pages = 4963–7 | doi = 10.1021/ja01116a024 }}</ref> when a large group of N-substituted morphine analogues were characterized for activity. The compound has relatively little opioid activity in its own right,<ref>{{cite journal | vauthors = Fraser HF, Wikler A, Van Horn GD, Eisenman AJ, Isbell H | title = Human pharmacology and addiction liability of normorphine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 122 | issue = 3 | pages = 359–69 | date = March 1958 | pmid = 13539761 }}</ref><ref>{{cite journal | vauthors = Lasagna L, De Kornfeld TJ | title = Analgesic potency of normorphine in patients with postoperative pain | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 124 | issue = 3 | pages = 260–3 | date = November 1958 | pmid = 13588540 }}</ref> but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine.<ref>{{cite journal | vauthors = Yeh SY | title = Urinary excretion of morphine and its metabolites in morphine-dependent subjects | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 192 | issue = 1 | pages = 201–10 | date = January 1975 | pmid = 235634 }}</ref> with its formation from morphine catalyzed by the liver enzymes CYP3A4 and CYP2C8.<ref>{{cite journal | vauthors = Projean D, Morin PE, Tu TM, Ducharme J | title = Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 33 | issue = 8 | pages = 841–54 | date = August 2003 | pmid = 12936704 | doi = 10.1080/0049825031000121608 | s2cid = 41467595 }}</ref>
Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grams in 2014, unchanged from the prior year. The salts in use are the free base hexahydrate (free base conversion ratio 0.715), and hydrochloride (0.833).<ref>{{Cite web | url=http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | title=Quotas - 2014 | work=DEA Diversion Control Division | access-date=2016-02-27 | archive-date=2016-03-04 | archive-url=https://web.archive.org/web/20160304053357/http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | url-status=dead }}</ref>
== References == {{Reflist}}
{{Opioidergics}}
Category:4,5-Epoxymorphinans Category:Opiates Category:Hydroxyarenes Category:Secondary alcohols Category:Opioid metabolites