{{Short description|Chemical compound}} {{more citations needed|date=June 2010}} {{Drugbox | Verifiedfields = | verifiedrevid = | IUPAC_name = (5α)-17-Methyl-4,5-epoxymorphinan-3,6,14-triol | image =Oxymorphol Structure.svg | image_class = skin-invert-image <!--Clinical data--> | tradename = | Drugs.com = | MedlinePlus = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = | legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_CA = | legal_UK = | legal_US = | dependency_liability = | routes_of_administration = <!--Pharmacokinetic data--> | bioavailability = | metabolism = hepatic | elimination_half-life = | excretion = <!--Identifiers--> | CAS_number_Ref = | CAS_number = 54934-75-7 | ATC_prefix = N02 | ATC_suffix = A | PubChem = 6712731 | DrugBank = | ChemSpiderID = 5144767 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 67P6D5Q6YK | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1968360 <!--Chemical data--> | C=17 | H=21 | N=1 | O=4 | smiles = CN1CC[C@]23c4c5ccc(c4O[C@H]2C(CC[C@]3([C@H]1C5)O)O)O | StdInChI = 1S/C17H21NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,11-12,15,19-21H,4-8H2,1H3/t11?,12-,15+,16+,17-/m1/s1 | StdInChIKey = AABLHGPVOULICI-ZOFKVTQNSA-N | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | synonyms = 4,5α-Epoxy-17-methylmorphinan-3,6,14-triol }}
'''Oxymorphol''' is oxymorphone which has been hydrogenated at the 6-position and consists of a mixture of 4,5α-epoxy-17-methylmorphinan-3,6β,14-triol and 4,5α-epoxy-17-methylmorphinan-3,6α,14-triol (hydromorphinol).<ref>{{cite web | url = http://www.chemicalbook.com/ProductChemicalPropertiesCB0933076_EN.htm | title = α-Oxymorphol as "Hydromorphinol"}}</ref> It is produced by the human body as an active metabolite of oxymorphone and some bacteria as an intermediate in turning morphine into hydromorphone.<ref name="pmid6194952">{{cite journal | vauthors = Cone EJ, Darwin WD, Buchwald WF, Gorodetzky CW | title = Oxymorphone metabolism and urinary excretion in human, rat, guinea pig, rabbit, and dog | journal = Drug Metabolism and Disposition: The Biological Fate of Chemicals | volume = 11 | issue = 5 | pages = 446–50 | date = 1983 | pmid = 6194952 | doi = 10.1016/S0090-9556(25)08048-1| url = }}</ref> It can also be manufactured and is the subject of patents by drug companies looking for new semi-synthetic analgesics and cough suppressants.
A derivative of oxymorphol, 8-hydroxy-6-α-oxymorphol, was discovered in the first decade of the 21st century and the subject of a patent application by Endo Pharmaceuticals for an analgesic and antitussive.<ref>{{cite web |url=http://www.faqs.org/patents/app/20090018154 |title=OPIOID AND METHODS OF MAKING AND USING THE SAME - Patent application |website=www.faqs.org |url-status=dead |archive-url=https://web.archive.org/web/20140502004853/http://www.faqs.org/patents/app/20090018154 |archive-date=2014-05-02}} </ref>
==References== {{Reflist}}
{{Opioidergics}}
Category:4,5-Epoxymorphinans Category:Opioid metabolites Category:Semisynthetic opioids Category:Mu-opioid receptor agonists