Dextrorphan

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Not to be confused with Dextromethorphan, 3-Methoxymorphinan, or Levomethorphan.
Dextrorphan
Dextrorphan.svg
Dextrorphane 3d.gif
Clinical data
ATC code none
Legal status
Legal status
  • US: Unscheduled
Identifiers
CAS Number 125-73-5 YesY
PubChem (CID) 5360697
ChemSpider 10489895 N
UNII 04B7QNO9WS N
ChEMBL CHEMBL341216 N
Chemical and physical data
Formula C17H23NO
Molar mass 257.371 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

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]

Pharmacology[edit]

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.[12] 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.[citation needed]

Legality[edit]

Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.[13]

See also[edit]

References[edit]

  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. doi:10.1097/00004714-199808000-00014. PMID 9690700. 
  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. doi:10.1016/0304-3940(88)90362-X. PMID 2897648. 
  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. doi:10.1139/y89-090. PMID 2673498. 
  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. doi:10.1097/ANA.0b013e31817f523f. PMID 18812887. 
  5. ^ a b Lauterbach, Edward C. (2012-06-01). "An extension of hypotheses regarding rapid-acting, treatment-refractory, and conventional antidepressant activity of dextromethorphan and dextrorphan". Medical Hypotheses. 78 (6): 693–702. doi:10.1016/j.mehy.2012.02.012. ISSN 1532-2777. PMID 22401777. 
  6. ^ 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. doi:10.1016/S0006-8993(96)01254-1. PMID 9037429. 
  7. ^ 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. doi:10.1016/S0006-8993(99)01125-7. PMID 10064839. 
  8. ^ 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". ACS Chemical Neuroscience. 5 (2): 93–99. doi:10.1021/cn400205z. PMC 3930996Freely accessible. PMID 24393077. 
  9. ^ 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. doi:10.1124/jpet.104.075093. PMID 15356218. 
  10. ^ 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. PMID 10869398. 
  11. ^ 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. doi:10.1016/S0166-4328(00)00372-7. PMID 11182165. 
  12. ^ 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. doi:10.1124/jpet.103.060038. PMID 14742749. 
  13. ^ DEA. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). Retrieved 2010-09-24.