Dextrorphan

Dextrorphan

Dextrorphan
Systematic (IUPAC) name
(+)-17-methyl-9a,13a,14a-morphinan-3-ol
Clinical data
Legal status
  • US: Unscheduled
Identifiers
CAS Registry Number  Y
ATC code None
PubChem CID:
ChemSpider  N
UNII  N
ChEMBL  N
Chemical data
Formula C17H23NO
Molecular mass 257.371 g/mol
 N   

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.[1]

Contents

  • Pharmacology 1
  • Legality 2
  • See also 3
  • References 4

Pharmacology

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.[11]

Legality

Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.[12]

See also

References

  1. ^ Zawertailo, L. A.; Kaplan, H. L.; Busto, U. E.; Tyndale, R. F.; Sellers, E. M. (Aug 1998). "Psychotropic Effects of Dextromethorphan are Altered by the CYP2D6 Polymorphism: A Pilot Study". Journal of Clinical Psychopharmacology 18 (4): 332–337.  
  2. ^ Wong, B. Y.; Coulter, D. A.; Choi, D. W.; Prince, D. A. (Feb 1988). "Dextrorphan and Dextromethorphan, Common Antitussives, are Antiepileptic and Antagonize N-Methyl-D-Aspartate in Brain Slices". Neuroscience Letters 85 (2): 261–266.  
  3. ^ Church, J.; Jones, M. G.; Davies, S. N.; Lodge, D. (Jun 1989). "Antitussive Agents as N-Methylaspartate Antagonists: Further Studies". Canadian Journal of Physiology and Pharmacology 67 (6): 561–567.  
  4. ^ a b Kamel, I. R.; Wendling, W. W.; Chen, D.; Wendling, K. S.; Harakal, C.; Carlsson, C. (Oct 2008). "N-Methyl-D-Aspartate (NMDA) Antagonists -- S(+)-Ketamine, Dextrorphan, and Dextromethorphan -- Act as Calcium Antagonists on Bovine Cerebral Arteries". Journal of Neurosurgical Anesthesiology 20 (4): 241–248.  
  5. ^ Richter, A.; Löscher, W. (Jan 1997). "Dextrorphan, but not Dextromethorphan, Exerts Weak Antidystonic Effects in Mutant Dystonic Hamsters". Brain Research 745 (1–2): 336–338.  
  6. ^ Chou, Y. C.; Liao, J. F.; Chang, W. Y.; Lin, M. F.; Chen, C. F. (Mar 1999). "Binding of Dimemorfan to Sigma-1 Receptor and its Anticonvulsant and Locomotor Effects in Mice, Compared with Dextromethorphan and Dextrorphan". Brain Research 821 (2): 516–519.  
  7. ^ Anna W. Sromek; Brian A. Provencher; Shayla Russell; Elena Chartoff; Brian I. Knapp; Jean M. Bidlack; John L. Neumeyer (January 2014). "Preliminary Pharmacological Evaluation of Enantiomeric Morphinans" (HTML). ACS Chemical Neuroscience 5(2). 
  8. ^ Damaj, M. I.; Flood, P.; Ho, K. K.; May, E. L.; Martin, B. R. (Feb 2005). "Effect of Dextrometorphan and Dextrorphan on Nicotine and Neuronal Nicotinic Receptors: in Vitro and in Vivo Selectivity" (pdf). The Journal of Pharmacology and Experimental Therapeutics 312 (2): 780–785.  
  9. ^ Hernandez, S. C.; Bertolino, M.; Xiao, Y.; Pringle, K. E.; Caruso, F. S.; Kellar, K. J. (2000). "Dextromethorphan and its Metabolite Dextrorphan Block alpha3beta4 Neuronal Nicotinic Receptors" (pdf). Journal of Pharmacology and Experimental Therapeutics 293 (3): 962–967.  
  10. ^ Kim, H. C.; Ko, K. H.; Kim, W. K.; Shin, E. J.; Kang, K. S.; Shin, C. Y.; Jhoo, W. K. (May 2001). "Effects of Dextromethorphan on the Seizures Induced by Kainate and the Calcium Channel Agonist BAY k-8644: Comparison with the Effects of Dextrorphan". Behavioural Brain Research 120 (2): 169–175.  
  11. ^ Pechnick, R. N.; Poland, R. E. (2004). "Comparison of the Effects of Dextromethorphan, Dextrorphan, and Levorphanol on the Hypothalamo-Pituitary-Adrenal Axis" (pdf). Journal of Pharmacology And Experimental Therapeutics 309 (2): 515–522.  
  12. ^ DEA. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). Retrieved 2010-09-24.