Dextrorphan

Dextrorphan

Clinical data
ATC code	none
Legal status
Legal status	US: Unscheduled
Identifiers
IUPAC name (+)-17-methyl-9a,13a,14a-morphinan-3-ol
CAS Number	125-73-5 Y
PubChem CID	5360697
ChemSpider	10489895 N
UNII	04B7QNO9WS
ChEMBL	CHEMBL341216 N
ECHA InfoCard	100.004.323
Chemical and physical data
Formula	C17H23NO
Molar mass	257.371 g/mol
3D model (Jmol)	Interactive image
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?)

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.

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. Dextrorphan has a notably longer half-life than its parent compound, and therefore has a tendency to accumulate in the blood after repeated administration of normally dosed dextromethorphan formulations.

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