3-Hydroxymorphinan

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Chemical compound

title: "3-Hydroxymorphinan" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hydroxyarenes", "morphinans", "opioids", "human-drug-metabolites"] description: "Chemical compound" topic_path: "general/hydroxyarenes" source: "https://en.wikipedia.org/wiki/3-Hydroxymorphinan" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | verifiedrevid = 477344702 | IUPAC_name = (±)-morphinan-3-ol | image = 3-Hydroxymorphinan.png | image_class = skin-invert-image | alt = Skeletal formula | width = 180 | image2 = 3-Hydroxymorphinan molecule ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model | CAS_number_Ref = | CAS_number = 39131-41-4 | UNII_Ref = | UNII = E4S6LA88PG | ATC_prefix = None | ATC_suffix = | PubChem = | ChemSpiderID_Ref = | ChemSpiderID = 16735936 | C = 16 | H = 21 | N = 1 | O = 1 | smiles = Oc3ccc4C[C@H]1NCC[C@@]2(CCCC[C@@H]12)c4c3 | StdInChI_Ref = | StdInChI = 1S/C16H21NO/c18-12-5-4-11-9-15-13-3-1-2-6-16(13,7-8-17-15)14(11)10-12/h4-5,10,13,15,17-18H,1-3,6-9H2/t13-,15+,16+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = IYNWSQDZXMGGGI-NUEKZKHPSA-N | bioavailability = 18% | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_category = | legal_status = | routes_of_administration =

3-Hydroxymorphinan (3-HM), or morphinan-3-ol, is a psychoactive drug of the morphinan family. It is the racemic counterpart to norlevorphanol.

The dextrorotatory stereoisomer of the compound is an active metabolite of dextromethorphan, dextrorphan, and 3-methoxymorphinan, and similarly to them has potent neuroprotective and neurotrophic effects on LTS- and MPTP-treated dopaminergic neurons of the nigrostriatal pathway, but notably without producing any neuropsychotoxic side effects (e.g., dissociation or hallucinations) or having any anticonvulsant actions. It does not seem to bind to the NMDA receptor, and instead, its neuroprotective properties appear result from inhibition of glutamate release via the suppression of presynaptic voltage-dependent Ca2+ entry and protein kinase C activity. In any case, as such, the compound has been investigated as a potential management of Parkinson's disease medication (antiparkinsonian agent). A prodrug, GCC1290K, has been developed on account of 3-HM's poor bioavailability (18%), and a New Drug Application has been approved for it by the United States Food and Drug Administration. It is currently undergoing clinical trials for the treatment of Parkinson's disease. It does not have a Controlled Substances Act 1970 schedule, ACSCN, or annual aggregate manufacturing quota and may not necessarily be controlled, whilst norlevorphanol is; none of the dextrorotary derivatives of the dromoran and norlevorphanol sub-families of morphinan derivatives are controlled as they do not have opioid activity but the other racemic compounds are.

3-HM's levorotatory stereoisomer, norlevorphanol, in contrast to (+)-3-HM, is an opioid analgesic. It was never marketed as such however, probably due to a combination of the facts that norlevorphanol has low bioavailability and that its potency is diminished compared to its N-methylated analogue levorphanol. ::figure[src="https://upload.wikimedia.org/wikipedia/commons/4/4f/(+)-3-Hydroxymorphinan.png" caption="(+)-3-Hydroxymorphinan the Dextro isomer of 3-hydroxymorphinan. The Dextro form is metabolite of 3-methoxymorphinan which is metabolite of Dextromethorphan"] ::

References

References

  1. (1997). "Dictionary of pharmacological agents". CRC Press.
  2. (1992). "Cytochrome P450-dependent metabolism of dextromethorphan: fetal and adult studies". Developmental Pharmacology and Therapeutics.
  3. (March 2005). "3-hydroxymorphinan is neurotrophic to dopaminergic neurons and is also neuroprotective against LPS-induced neurotoxicity". The FASEB Journal.
  4. (December 2006). "3-Hydroxymorphinan, a metabolite of dextromethorphan, protects nigrostriatal pathway against MPTP-elicited damage both in vivo and in vitro". The FASEB Journal.
  5. (January 2008). "Neuropsychotoxicity of abused drugs: potential of dextromethorphan and novel neuroprotective analogs of dextromethorphan with improved safety profiles in terms of abuse and neuroprotective effects". Journal of Pharmacological Sciences.
  6. (2011). "Neuropsychotoxic and neuroprotective potentials of dextromethorphan and its analogs". Journal of Pharmacological Sciences.
  7. (July 2009). "Inhibitory effect of glutamate release from rat cerebrocortical synaptosomes by dextromethorphan and its metabolite 3-hydroxymorphinan". Neurochemistry International.
  8. "Conversion Factors for Controlled Substances". Drug Enforcement Agency, U.S. Department of Justice.
  9. (1996). "Dictionary of organic compounds". Chapman & Hall.
  10. Bentham Science Publishers. (April 1995). "Current Medicinal Chemistry". Bentham Science Publishers.

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hydroxyarenesmorphinansopioidshuman-drug-metabolites