Nowadays, Dextrorphan is a topic that has captured the attention of many people around the world. Since its emergence, Dextrorphan has generated great interest and been the subject of debate in various circles. Over the years, Dextrorphan has proven to be relevant in various areas, from technology to politics, culture and society in general. As we continue to explore and analyze Dextrorphan, it is imperative to understand its impact on our daily lives and the world around us. In this article, we will delve into the importance of Dextrorphan and its influence on different aspects of contemporary society.
Clinical data | |
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Other names | DXO, Dextrorphanol |
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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 in high doses a dissociative hallucinogen. It is the dextrorotatory enantiomer of racemorphan; the levorotatory enantiomer is levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan.
Site | Ki (nM) | Species | Ref |
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NMDAR (MK-801) |
486–906 | Rat | |
σ1 | 118–481 | Rat | |
σ2 | 11,325–15,582 | Rat | |
MORTooltip μ-Opioid receptor | 420 >1,000 |
Rat Human |
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DORTooltip δ-Opioid receptor | 34,700 | Rat | |
KORTooltip κ-Opioid receptor | 5,950 | Rat | |
SERTTooltip Serotonin transporter | 401–484 | Rat | |
NETTooltip Norepinephrine transporter | ≥340 | Rat | |
DATTooltip Dopamine transporter | >1,000 | Rat | |
5-HT1A | >1,000 | Rat | |
5-HT1B/1D | 54% at 1 μM | Rat | |
5-HT2A | >1,000 | Rat | |
α1 | >1,000 | Rat | |
α2 | >1,000 | Rat | |
β | 35% at 1 μM | Rat | |
D2 | >1,000 | Rat | |
H1 | 95% at 1 μM | Rat | |
mAChRsTooltip Muscarinic acetylcholine receptors | 100% at 1 μM | Rat | |
nAChRsTooltip Nicotinic acetylcholine receptors | 1,300–29,600 (IC50) |
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VDSCsTooltip Voltage-dependent sodium channels | 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. It also has more affinity for the opioid receptors than dextromethorphan, significantly so at high doses.
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] It is further converted to 3-HM by CYP3A4 or glucuronidated.
Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.
Dextrorphan was under development for the treatment of stroke, and reached phase II clinical trials for this indication, but development was discontinued.
In 2021, dextrorphan was identified in >75% of sludge samples taken from 12 wastewater treatment plants in California. The same study associated dextrorphan with estrogenic activity by using predictive modelling, before observing it in in vitro.
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