Dextrallorphan

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Dextrallorphan
Dextrallorphan.svg
Systematic (IUPAC) name
(+)-(13α,14α)-17-allylmorphinan-3-ol
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Identifiers
CAS number 5822-43-5
ATC code None
PubChem CID 5748237
ChemSpider 2339009
Chemical data
Formula C19H25NO 
Mol. mass 283.41 g/mol

Dextrallorphan (DXA) is a drug of the morphinan class known 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.[5][2] As an NMDA receptor antagonist, in vivo, it is approximately twice as potent as dextromethorphan, and five-fold less potent than dextrorphan.[3]

See also[edit]

References[edit]

  1. ^ Su, T. P. (Nov 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): 284–290. PMID 6290634. 
  2. ^ a b Codd, E. E.; Shank, R. P.; Schupsky, J. J.; Raffa, R. B. (Sep 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): 1263–1270. PMID 7562497. 
  3. ^ a b Shukla, V. K.; Lemaire, S. (Jan 1997). "N-Methyl-D-Aspartate Antagonist Activity of Alpha- and Beta-Sulfallorphans" (pdf). The Journal of Pharmacology and Experimental Therapeutics 280 (1): 357–365. PMID 8996216. 
  4. ^ Shannon, H. E. (Apr 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): 144–152. PMID 6834266. 
  5. ^ He, X. S.; Bowen, W. D.; Lee, K. S.; Williams, W.; Weinberger, D. R.; de Costa, B. R. (Mar 1993). "Synthesis and Binding Characteristics of Potential SPECT Imaging Agents for Sigma-1 and Sigma-2 Binding Sites". Journal of Medicinal Chemistry 36 (5): 566–571. doi:10.1021/jm00057a006. PMID 8496936.