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
ATC code	None
PubChem	CID 5360697
UNII	04B7QNO9WS
ChEMBL	CHEMBL341216
Chemical data
Formula	C17H23NO
Mol. mass	257.371 g/mol
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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]

[edit] Pharmacology

Noncompetitive N-methyl-D-aspartate receptor (NMDAR) antagonist.^[2]^[3]^[4]
σ₁ and σ₂ sigma receptor agonist.^[5]^[6]
α₃β₄, α₄β₂, and α₇ nicotinic acetylcholine receptor antagonist.^[7]^[8]
L-Type voltage-gated calcium channel (LVGCC) blocker.^[4]^[9]

The pharmacology of dextrorphan is similar to that of dextromethorphan (DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist.^[10]

[edit] Legality

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

[edit] See also

[edit] References

^ 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.
^ 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.
^ 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.
^ ^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.
^ 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.
^ 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.
^ 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. http://jpet.aspetjournals.org/content/312/2/780.full.pdf.
^ 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. http://jpet.aspetjournals.org/content/293/3/962.full.pdf.
^ 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.
^ 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. http://jpet.aspetjournals.org/content/309/2/515.full.pdf.
^ DEA. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals". http://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. Retrieved 2010-09-24.

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[0] 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.

[pmid2897648-1] 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.

[pmid2673498-2] 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.

[pmid18812887-3] 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.

[pmid9037429-4] 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.

[pmid10064839-5] 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.

[pmid15356218-6] 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. http://jpet.aspetjournals.org/content/312/2/780.full.pdf.

[pmid10869398-7] 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. http://jpet.aspetjournals.org/content/293/3/962.full.pdf.

[pmid11182165-8] 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.

[9] 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. http://jpet.aspetjournals.org/content/309/2/515.full.pdf.

[urlDextrorphan_Legality-10] DEA. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals". http://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. Retrieved 2010-09-24.

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Dextrorphan

Contents

[edit] Pharmacology

[edit] Legality

[edit] See also

[edit] References

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