Oxymorphazone

Overview

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.[1–8] WP

Chemistry

Formula

C17H21N3O3 PC

CAS number

73697-35-5 PC

Molar mass (g/mol)

315.37 PC

IUPAC name (computed by PubChem)

(4R,4aS,7E,7aR,12bS)-7-hydrazinylidene-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol PC

SMILES

CN1CC[C@]23[C@@H]4/C(=N/N)/CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O PC

InChIKey

VOFTYIFRRWVMOO-FDUMSJNMSA-N PC

PubChem CID

9577748

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Galetta S, Ling GS, Wolfin L, Pasternak GW. Receptor binding and analgesic properties of oxymorphazone. Life Sciences. 1982. doi:10.1016/0024-3205(82)90388-5 · PMID 6183551
2. Journal / agency Hahn EF, Carroll-Buatti M, Pasternak GW. Irreversible opiate agonists and antagonists: the 14-hydroxydihydromorphinone azines. The Journal of Neuroscience. May 1982. doi:10.1523/JNEUROSCI.02-05-00572.1982 · PMID 6176696 · PMC6564265
3. Journal / agency France CP, Jacobson AE, Woods JH. Discriminative stimulus effects of reversible and irreversible opiate agonists: morphine, oxymorphazone and buprenorphine. The Journal of Pharmacology and Experimental Therapeutics. September 1984. doi:10.1016/S0022-3565(25)21704-9 · PMID 6206224
4. Journal / agency Ling GS, Galetta S, Pasternak GW. Oxymorphazone: a long-acting opiate analgesic. Cellular and Molecular Neurobiology. March 1984. doi:10.1007/BF00710938 · PMID 6204757 · PMC11572834
5. Journal / agency Williams CL, Bodnar RJ, Clark JE, Hahn EF, Burks TF, Pasternak GW. Irreversible opiate agonists and antagonists. IV. Analgesic actions of 14-hydroxydihydromorphinone hydrazones. The Journal of Pharmacology and Experimental Therapeutics. April 1988. doi:10.1016/S0022-3565(25)22279-0 · PMID 2452249
6. Journal / agency Benyhe S, Hoffmann G, Varga E, Hosztafi S, Toth G, Borsodi A, Wollemann M. Effects of oxymorphazone in frogs: long lasting antinociception in vivo, and apparently irreversible binding in vitro. Life Sciences. 1989. doi:10.1016/0024-3205(89)90302-0 · PMID 2472540
7. Journal / agency Marie N, Aguila B, Allouche S. Tracking the opioid receptors on the way of desensitization. Cellular Signalling. November 2006. doi:10.1016/j.cellsig.2006.03.015 · PMID 16750901
8. Journal / agency DuPen A, Shen D, Ersek M. Mechanisms of opioid-induced tolerance and hyperalgesia. Pain Management Nursing. September 2007. doi:10.1016/j.pmn.2007.02.004 · PMID 17723928

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.