Dextrorphan
Systematic (IUPAC) name | |
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(+)-17-methyl-9a,13a,14a-morphinan-3-ol
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Clinical data | |
Legal status |
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Identifiers | |
CAS Number | 125-73-5 |
ATC code | none |
PubChem | CID: 5360697 |
ChemSpider | 10489895 |
UNII | 04B7QNO9WS |
ChEMBL | CHEMBL341216 |
Chemical data | |
Formula | C17H23NO |
Molecular mass | 257.371 g/mol |
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Dextrorphan (DXO) is a psychoactive drug of the morphinan chemical 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]
Contents
Pharmacology
- Noncompetitive N-methyl-D-aspartate receptor (NMDAR) antagonist.[2][3][4]
- σ1 (118 nM)[5] and σ2 sigma receptor agonist.[6][7]
- Serotonin reuptake inhibitor (484 nM)[5]
- μ-, and κ-opioid receptor agonist [8]
- α3β4, α4β2, and α7 nicotinic acetylcholine receptor antagonist.[9][10]
- Glycine receptor antagonist
- L-Type voltage-gated calcium channel (LVGCC) blocker.[4][11]
The pharmacology of dextrorphan is similar to that of dextromethorphan (DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist as well as essentially inactive as a serotonin reuptake inhibitor, but retains DXMs activity as a norepinephrine reuptake inhibitor.[12]
Legality
Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.[13]
See also
- Cough medicine
- Dextrallorphan
- Dextromethorphan
- Dissociative
- Levallorphan
- Morphanol
- Morphinan
- Nortilidine
- O-Desmethyltramadol
- Oxilorphan
References
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- Morphinans
- Dissociative drugs
- Euphoriants
- Sigma agonists
- NMDA receptor antagonists
- Nicotinic antagonists
- Antitussives
- Phenols
- Enantiopure drugs
- Glycine receptor antagonists
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- Nervous system drug stubs