Dextrorphan

Dextrorphan

Systematic (IUPAC) name
(+)-17-methyl-9a,13a,14a-morphinan-3-ol
Clinical data
Legal status	US: Unscheduled
Identifiers
CAS Number	125-73-5 Y
ATC code	none
PubChem	CID: 5360697
ChemSpider	10489895 N
UNII	04B7QNO9WS N
ChEMBL	CHEMBL341216 N
Chemical data
Formula	C17H23NO
Molecular mass	257.371 g/mol
SMILES OC1=CC2=C(C[C@@H]3N(CC[C@@]42CCCC[C@H]34)C)C=C1
InChI InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1 N Key:JAQUASYNZVUNQP-PVAVHDDUSA-N N
NY (what is this?)  (verify)

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.

Pharmacology

• Noncompetitive N-methyl-D-aspartate receptor (NMDAR) antagonist.
• σ₁ (118 nM) and σ₂ sigma receptor agonist.
• Serotonin reuptake inhibitor (484 nM)
• μ-, and κ-opioid receptor agonist
• α₃β₄, α₄β₂, and α₇ nicotinic acetylcholine receptor antagonist.
• Glycine receptor antagonist
• L-Type voltage-gated calcium channel (LVGCC) blocker.

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.

Legality

Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.

See also

• Cough medicine
• Dextrallorphan
• Dextromethorphan
• Dissociative
• Levallorphan
• Morphanol
• Morphinan
• Nortilidine
• O-Desmethyltramadol
• Oxilorphan