Structure via PubChem · Public domain (PubChem)
dextrorphan
Sign in to saveAlso known as d-3-hydroxy-N-methylmorphinan, (+)-3-hydroxy-N-methylmorphinan, DXO, D-morphan
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.
In the Vinony graph
Vinony's link graph records 1,276 inbound references to dextrorphan, and connects out to antitussive, drug liberalization and Dissociative.
It is catalogued under topics including Antitussives, Chemical pages without DrugBank identifier and Dissociative drugs.
Vinony links it to 13 Wikipedia language editions.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 408496712
- Drug.IUPAC_name
- (+)-17-methyl-9a,13a,14a-morphinan-3-ol
- Drug.image
- Dextrorphan.svg
- Drug.image_class
- skin-invert-image
- Drug.legal_US
- Unscheduled
- Drug.CAS_number
- 125-73-5
- Drug.ATC_prefix
- None
- Drug.PubChem
- 5360697
- Drug.UNII
- 04B7QNO9WS
- Drug.ChEMBL
- 1254766
- Drug.ChemSpiderID
- 10489895
- Drug.synonyms
- DXO, Dextrorphanol
- Drug.C
- 17
- Drug.H
- 23
- Drug.N
- 1
- Drug.O
- 1
via Wikipedia infobox
Chemical data
- Formula
- C17H23NO
- Molecular weight
- 257.37 g/mol
- IUPAC name
- (1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
- SMILES
- CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC4=C3C=C(C=C4)O
- InChIKey
- JAQUASYNZVUNQP-PVAVHDDUSA-N
- XLogP
- 3.1
- Polar surface area
- 23.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
914 papers- Neurotoxicity of dextrorphan.Archives of medical research · 1999
- Dextrorphan and dextromethorphan attenuate glutamate neurotoxicity.Brain research · 1987
- Infant Dextromethorphan and Dextrorphan Exposure via Breast Milk From Mothers Who Are CYP2D6 Extensive Metabolizers.Journal of clinical pharmacology · 2022
- Evaluating dextrorphan as a wastewater biomarker for cough suppressant use: A longitudinal study in China.Water research · 2025
- Dopamine enhancement of dextrorphan-induced skin antinociception in response to needle pinpricks in rats.Pharmacological reports : PR · 2019
via PubMed
Wikidata facts
- Mass
- 257.177964
Show 6 more facts
via Wikidata · CC0
~3 min read
Encyclopedic overview
9 sectionsContents
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Society and culture
- Legal status
- Research
- Environmental presence
- See also
- References
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.
==Pharmacology==
Excerpted from Wikipedia’s “dextrorphan” article, available under the CC BY-SA 4.0 licence.