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Dextrorphan
Systematic (IUPAC) name
17-methyl-9a,13a,14a-morphinan-3-ol
Identifiers
CAS number 125-73-5
ATC code none
PubChem 5360697
Chemical data
Formula C17H23NO 
Mol. mass 257.371 g/mol
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US)

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 morphanol, the levo- halve being levorphanol. Dextrorphan is also the primary active metabolite of dextromethorphan (DXM), and is partially responsible for its clinical effects.

Contents

Pharmacology

The pharmacology of dextrorphan is similar to that of dextromethorphan. However, dextrorphan is much more potent of an NMDA receptor antagonist and much weaker as a serotonin reuptake inhibitor in comparison.[10] In regards to the above pharmacology, it should be noted that dextrorphan's opioid and serotonin and norepinephrine reuptake-inhibiting effects are probably too weak to be significant at normal doses.

Legality

Dextrorphan is a Schedule I controlled substance in the United States.[11]

See also

References

  1. ^ 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. PMID 2897648. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. PMID 9037429. http://linkinghub.elsevier.com/retrieve/pii/S0006-8993(96)01254-1. 
  5. ^ 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. PMID 10064839. http://linkinghub.elsevier.com/retrieve/pii/S0006-8993(99)01125-7. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ a b c 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". The Journal of Pharmacology and Experimental Therapeutics 274 (3): 1263–70. PMID 7562497. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7562497. 
  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. 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. "Dextrorphan Legality". http://www.usdoj.gov/dea/pubs/csa/812.htm. Retrieved 2009-08-07. 







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