Oxymorphol

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Chemical compound

title: "Oxymorphol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["4,5-epoxymorphinans", "opioid-metabolites", "semisynthetic-opioids", "mu-opioid-receptor-agonists"] description: "Chemical compound" topic_path: "general/4-5-epoxymorphinans" source: "https://en.wikipedia.org/wiki/Oxymorphol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = | verifiedrevid = | IUPAC_name = (5α)-17-Methyl-4,5-epoxymorphinan-3,6,14-triol | image =Oxymorphol Structure.svg | image_class = skin-invert-image | tradename = | Drugs.com = | MedlinePlus = | pregnancy_AU = | pregnancy_US = | legal_AU = | legal_CA = | legal_UK = | legal_US = | dependency_liability = | routes_of_administration = | bioavailability = | metabolism = hepatic | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 54934-75-7 | ATC_prefix = N02 | ATC_suffix = A | PubChem = 6712731 | DrugBank = | ChemSpiderID = 5144767 | UNII_Ref = | UNII = 67P6D5Q6YK | KEGG_Ref = | KEGG = | ChEMBL_Ref = | ChEMBL = 1968360 | 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 = | StdInChIKey_Ref = | 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). It is produced by the human body as an active metabolite of oxymorphone and some bacteria as an intermediate in turning morphine into hydromorphone. 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.

References

References

  1. "α-Oxymorphol as "Hydromorphinol"".
  2. (1983). "Oxymorphone metabolism and urinary excretion in human, rat, guinea pig, rabbit, and dog". Drug Metabolism and Disposition: The Biological Fate of Chemicals.
  3. "OPIOID AND METHODS OF MAKING AND USING THE SAME - Patent application".

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4,5-epoxymorphinansopioid-metabolitessemisynthetic-opioidsmu-opioid-receptor-agonists