Dextrorphan

Dextrorphan
Clinical data
Other namesDXO, Dextrorphanol
ATC code
  • None
Legal status
Legal status
  • US: Unscheduled[1]
Identifiers
  • (+)-17-methyl-9a,13a,14a-morphinan-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.323 Edit this at Wikidata
Chemical and physical data
FormulaC17H23NO
Molar mass257.377 g·mol−1
3D model (JSmol)
  • CN1CC[C@@]23CCCC[C@@H]2[C@@H]1Cc4c3cc(O)cc4
  • 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
 ☒NcheckY (what is this?)  (verify)

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.[2]

  1. ^ Bensinger, Peter (October 1, 1976). "Dextrophan and Nalbuphine; Removal from Schedules" (PDF). NARA. Retrieved June 26, 2023.
  2. ^ Zawertailo LA, Kaplan HL, Busto UE, Tyndale RF, Sellers EM (August 1998). "Psychotropic effects of dextromethorphan are altered by the CYP2D6 polymorphism: a pilot study". Journal of Clinical Psychopharmacology. 18 (4): 332–337. doi:10.1097/00004714-199808000-00014. PMID 9690700.