Dextrorphan

Dextrorphan
Systematic (IUPAC) name
(+)-17-methyl- 9a,13a,14a-morphinan- 3-ol
Clinical data
Pregnancy cat.  ?
Legal status  ? (US)
Identifiers
CAS number 125-73-5 YesY
ATC code None
PubChem CID 5360697
UNII 04B7QNO9WS N
ChEMBL CHEMBL341216 N
Chemical data
Formula C17H23NO 
Mol. mass 257.371 g/mol
 N(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 dextro-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 abuse liability of dextromethorphan.[1]

Contents

Pharmacology

The pharmacology of dextrorphan is similar to that of dextromethorphan (DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist and much weaker as a serotonin reuptake inhibitor, producing a noticeably more body-affecting, "stoned" feeling[10].

Legality

Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.[11]

See also

References

  1. ^ 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): 332–7. PMID 9690700. http://www.ncbi.nlm.nih.gov/pubmed/9690700. 
  2. ^ Wong BY, Coulter DA, Choi DW, Prince DA (February 1988). "Dextrorphan and dextromethorphan, common antitussives, are antiepileptic and antagonize N-methyl-D-aspartate in brain slices". Neuroscience Letters 85 (2): 261–6. doi:10.1016/0304-3940(88)90362-X. PMID 2897648. 
  3. ^ Church J, Jones MG, Davies SN, Lodge D (June 1989). "Antitussive agents as N-methylaspartate antagonists: further studies". Canadian Journal of Physiology and Pharmacology 67 (6): 561–7. PMID 2673498. 
  4. ^ a b Kamel IR, Wendling WW, Chen D, Wendling KS, Harakal C, Carlsson C (October 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): 241–8. doi:10.1097/ANA.0b013e31817f523f. PMID 18812887. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0898-4921&volume=20&issue=4&spage=241. 
  5. ^ Richter A, Löscher W (January 1997). "Dextrorphan, but not dextromethorphan, exerts weak antidystonic effects in mutant dystonic hamsters". Brain Research 745 (1-2): 336–8. doi:10.1016/S0006-8993(96)01254-1. PMID 9037429. http://linkinghub.elsevier.com/retrieve/pii/S0006-8993(96)01254-1. 
  6. ^ Chou YC, Liao JF, Chang WY, Lin MF, Chen CF (March 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): 516–9. doi:10.1016/S0006-8993(99)01125-7. PMID 10064839. http://linkinghub.elsevier.com/retrieve/pii/S0006-8993(99)01125-7. 
  7. ^ Damaj MI, Flood P, Ho KK, May EL, Martin BR (February 2005). "Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity". The Journal of Pharmacology and Experimental Therapeutics 312 (2): 780–5. doi:10.1124/jpet.104.075093. PMID 15356218. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15356218. 
  8. ^ Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ (2000). "Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors". J. Pharmacol. Exp. Ther. 293 (3): 962–7. PMID 10869398. 
  9. ^ Kim HC, Ko KH, Kim WK, et al. (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): 169–75. doi:10.1016/S0166-4328(00)00372-7. PMID 11182165. http://linkinghub.elsevier.com/retrieve/pii/S0166432800003727. 
  10. ^ "Comparison of the Effects of Dextromethorphan, Dextrorphan, and Levorphanol on the Hypothalamo-Pituitary-Adrenal Axis -- Pechnick and Poland 309 (2): 515 -- Journal of Pharmacology And Experimental Therapeutics". http://jpet.aspetjournals.org/cgi/content/full/309/2/515?ijkey=73c6efcf7713b02798c855b5ce4d50f1aa22d299&keytype2=tf_ipsecsha#ABS. 
  11. ^ DEA. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals". http://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. Retrieved 2010-09-024.