Clinical data | |
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ATC code |
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Pharmacokinetic data | |
Bioavailability | 18% |
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ChemSpider | |
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Chemical and physical data | |
Formula | C16H21NO |
Molar mass | 243.350 g·mol−1 |
3D model ( JSmol) | |
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(what is this?) (verify) |
3-Hydroxymorphinan (3-HM), or morphinan-3-ol, is a psychoactive drug of the morphinan family. [1] It is the racemic counterpart to norlevorphanol.
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]
Clinical data | |
---|---|
ATC code |
|
Pharmacokinetic data | |
Bioavailability | 18% |
Identifiers | |
| |
CAS Number | |
ChemSpider | |
UNII | |
Chemical and physical data | |
Formula | C16H21NO |
Molar mass | 243.350 g·mol−1 |
3D model ( JSmol) | |
| |
| |
(what is this?) (verify) |
3-Hydroxymorphinan (3-HM), or morphinan-3-ol, is a psychoactive drug of the morphinan family. [1] It is the racemic counterpart to norlevorphanol.
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]