Oxymorphazone

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title: "Oxymorphazone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["4,5-epoxymorphinans", "poisons", "hydroxyarenes", "tertiary-alcohols", "cyclohexanols", "mu-opioid-receptor-agonists", "semisynthetic-opioids", "hydrazones", "alkylating-agents", "irreversible-agonists"] description: "Opioid analgesic" topic_path: "general/4-5-epoxymorphinans" source: "https://en.wikipedia.org/wiki/Oxymorphazone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Opioid analgesic ::

| Watchedfields = changed | verifiedrevid = 450847871 | IUPAC_name = (5α,6E)-3,14-dihydroxy-17-methyl-4,5-epoxy-morphinan-6-one hydrazone | image = Oxymorphazone.svg | image_class = skin-invert-image | image2 = Oxymorphazone BS.png

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 73697-35-5 | UNII_Ref = | UNII = 9J727K8R3U | ATC_prefix = none | ATC_suffix = | PubChem = 9577748 | DrugBank_Ref = | DrugBank = | ChemSpiderID = 23231158

| C=17 | H=21 | N=3 | O=3 | smiles = CN1CC[C@]23[C@@H]4/C(=N/N)/CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O | StdInChI = 1S/C17H21N3O3/c1-20-7-6-16-13-9-2-3-11(21)14(13)23-15(16)10(19-18)4-5-17(16,22)12(20)8-9/h2-3,12,15,21-22H,4-8,18H2,1H3/b19-10-/t12-,15+,16+,17-/m1/s1 | StdInChIKey = VOFTYIFRRWVMOO-YKKXUTDFSA-N

| synonyms = Oxymorphone hydrazone

Oxymorphazone is an opioid analgesic drug related to oxymorphone. Oxymorphazone is a potent and long acting μ-opioid agonist which binds irreversibly to the receptor, forming a covalent bond which prevents it from detaching once bound. This gives it an unusual pharmacological profile, and while oxymorphazone is only around half the potency of oxymorphone, with higher doses the analgesic effect becomes extremely long lasting, with a duration of up to 48 hours when administered intraventricularly. However, tolerance to analgesia develops rapidly with repeated doses, as chronically activated opioid receptors are rapidly internalised by β-arrestins, similar to the results of non-covalent binding by repeated doses of agonists with extremely high binding affinity such as lofentanil.

References

References

1. (1982). "Receptor binding and analgesic properties of oxymorphazone". Life Sciences.
2. (May 1982). "Irreversible opiate agonists and antagonists: the 14-hydroxydihydromorphinone azines". The Journal of Neuroscience.
3. (September 1984). "Discriminative stimulus effects of reversible and irreversible opiate agonists: morphine, oxymorphazone and buprenorphine". The Journal of Pharmacology and Experimental Therapeutics.
4. (March 1984). "Oxymorphazone: a long-acting opiate analgesic". Cellular and Molecular Neurobiology.
5. (April 1988). "Irreversible opiate agonists and antagonists. IV. Analgesic actions of 14-hydroxydihydromorphinone hydrazones". The Journal of Pharmacology and Experimental Therapeutics.
6. (1989). "Effects of oxymorphazone in frogs: long lasting antinociception in vivo, and apparently irreversible binding in vitro". Life Sciences.
7. (November 2006). "Tracking the opioid receptors on the way of desensitization". Cellular Signalling.
8. (September 2007). "Mechanisms of opioid-induced tolerance and hyperalgesia". Pain Management Nursing.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::