3-Hydroxymorphinan

3-Hydroxymorphinan (3-HM), or morphinan-3-ol, is a psychoactive drug of the morphinan family.^[1] It is the racemic counterpart to norlevorphanol.

ATC code

• None

Bioavailability18%

CAS Number

• 39131-41-4 ^Y

ChemSpider

• 16735936 ^Y

Quick facts Clinical data, ATC code ...

3-Hydroxymorphinan

Clinical data
ATC code	None
Pharmacokinetic data
Bioavailability	18%
Identifiers
IUPAC name (±)-morphinan-3-ol
CAS Number	39131-41-4 Y
ChemSpider	16735936 Y
UNII	E4S6LA88PG
Chemical and physical data
Formula	C16H21NO
Molar mass	243.350 g·mol−1
3D model (JSmol)	Interactive image
SMILES Oc3ccc4C[C@H]1NCC[C@@]2(CCCC[C@@H]12)c4c3
InChI InChI=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 Y Key:IYNWSQDZXMGGGI-NUEKZKHPSA-N Y
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The dextrorotatory stereoisomer of the compound is an active metabolite of dextromethorphan, dextrorphan, and 3-methoxymorphinan,^[2] and similarly to them has potent neuroprotective and neurotrophic effects on LTS- and MPTP-treated dopaminergic neurons of the nigrostriatal pathway,^[3][4] but notably without producing any neuropsychotoxic side effects (e.g., dissociation or hallucinations) or having any anticonvulsant actions.^[5][6] It does not seem to bind to the NMDA receptor,^[6] 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.^[7] 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.^[6] It is currently undergoing clinical trials for the treatment of Parkinson's disease.^[6] 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.^[8]

3-HM's levorotatory stereoisomer, norlevorphanol, in contrast to (+)-3-HM, is an opioid analgesic.^[9] 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.^[10]