Dextrallorphan

Dextrallorphan
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (+)-(13α,14α)-17-allylmorphinan-3-ol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC19H25NO
Molar mass283.415 g·mol−1
3D model (JSmol)
  • Oc1ccc3c(c1)[C@]24[C@@H]([C@H](N(CC2)C\C=C)C3)CCCC4

Dextrallorphan (DXA) is a chemical of the morphinan class that is used in scientific research. It acts as a σ1 receptor agonist and NMDA receptor antagonist.[1][2][3][4] It has no significant affinity for the σ2, μ-opioid, or δ-opioid receptor, or for the serotonin or norepinephrine transporter.[2][5] As an NMDA receptor antagonist, in vivo, it is approximately twice as potent as dextromethorphan, and five-fold less potent than dextrorphan.[3]

  1. ^ Su TP (November 1982). "Evidence for sigma opioid receptor: binding of [3H]SKF-10047 to etorphine-inaccessible sites in guinea-pig brain" (PDF). The Journal of Pharmacology and Experimental Therapeutics. 223 (2): 284–90. PMID 6290634.
  2. ^ a b Codd EE, Shank RP, Schupsky JJ, Raffa RB (September 1995). "Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception" (PDF). The Journal of Pharmacology and Experimental Therapeutics. 274 (3): 1263–70. PMID 7562497.
  3. ^ a b Shukla VK, Lemaire S (January 1997). "N-methyl-D-aspartate antagonist activity of alpha- and beta-sulfallorphans" (PDF). The Journal of Pharmacology and Experimental Therapeutics. 280 (1): 357–65. PMID 8996216.
  4. ^ Shannon HE (April 1983). "Pharmacological evaluation of N-allynormetazocine (SKF 10,047) on the basis of its discriminative stimulus properties in the rat". The Journal of Pharmacology and Experimental Therapeutics. 225 (1): 144–52. PMID 6834266.
  5. ^ He XS, Bowen WD, Lee KS, Williams W, Weinberger DR, de Costa BR (March 1993). "Synthesis and binding characteristics of potential SPECT imaging agents for sigma-1 and sigma-2 binding sites". Journal of Medicinal Chemistry. 36 (5): 566–71. doi:10.1021/jm00057a006. PMID 8496936.