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Clinical data | |
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Other names | DXO |
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ECHA InfoCard | 100.004.323 ![]() |
Chemical and physical data | |
Formula | C17H23NO |
Molar mass | 257.377 g·mol−1 |
3D model (JSmol) | |
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Dextrorphan (DXO) is a psychoactive drug of the morphinan class which acts as an antitussive or cough suppressant and dissociative hallucinogen. It is the dextrorotatory-stereoisomer of racemorphan, the levo-half being levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan.[1]
Site | Ki (nM) | Species | Ref |
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NMDAR (MK-801) |
486–906 | Rat | [3] |
σ1 | 118–481 | Rat | [3] |
σ2 | 11,325–15,582 | Rat | [3] |
MOR | 420 >1,000 |
Rat Human |
[3][6] |
DOR | 34,700 | Rat | [3] |
KOR | 5,950 | Rat | [3] |
SERT | 401–484 | Rat | [3] |
NET | ≥340 | Rat | [3] |
DAT | >1,000 | Rat | [3] |
5-HT1A | >1,000 | Rat | [3] |
5-HT1B/1D | 54% at 1 μM | Rat | [3] |
5-HT2A | >1,000 | Rat | [3] |
α1 | >1,000 | Rat | [3] |
α2 | >1,000 | Rat | [3] |
β | 35% at 1 μM | Rat | [3] |
D2 | >1,000 | Rat | [3] |
H1 | 95% at 1 μM | Rat | [3] |
mAChRs | 100% at 1 μM | Rat | [3] |
nAChRs | 1,300–29,600 (IC50) |
Rat | [3] |
VDSCs | ND | ND | ND |
Values are Ki (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site. |
The pharmacology of dextrorphan is similar to that of dextromethorphan (DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist as well much less active as a serotonin reuptake inhibitor, but retains DXM's activity as a norepinephrine reuptake inhibitor.[7]
Dextrorphan has a notably longer elimination half-life than its parent compound, and therefore has a tendency to accumulate in the blood after repeated administration of normally dosed dextromethorphan formulations.[citation needed]
Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.[8]
Dextrorphan was under development for the treatment of stroke, and reached phase II clinical trials for this indication, but development was discontinued.[9]
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