Dextrorphan
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| Clinical data | |
|---|---|
| ATC code | none |
| Legal status | |
| Legal status |
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| Identifiers | |
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| CAS Number |
125-73-5  |
| PubChem (CID) | 5360697 |
| ChemSpider |
10489895  |
| UNII |
04B7QNO9WS |
| ChEMBL |
CHEMBL341216 |
| ECHA InfoCard | 100.004.323 |
| Chemical and physical data | |
| Formula | C17H23NO |
| Molar mass | 257.371 g/mol |
| 3D model (Jmol) | Interactive image |
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| (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
- Noncompetitive N-methyl-D-aspartate receptor (NMDAR) antagonist.[2][3][4]
- σ1 (118 nM)[5] and σ2 sigma receptor agonist.[6][7]
- Serotonin reuptake inhibitor (484 nM)[5]
- μ-, and κ-opioid receptor agonist [8]
- α3β4, α4β2, and α7 nicotinic acetylcholine receptor antagonist.[9][10]
- Glycine receptor antagonist
- L-Type voltage-gated calcium channel (LVGCC) blocker.[4][11]
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.
Legality
Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.[13]
See also
- Cough medicine
- Dextrallorphan
- Dextromethorphan
- Dissociative
- Levallorphan
- Morphanol
- Morphinan
- Nortilidine
- O-Desmethyltramadol
- Oxilorphan
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.
- 1 2 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.
- 1 2 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.
- ↑ 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.
- ↑ 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 3930996
. PMID 24393077. - ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ DEA. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). Retrieved 2010-09-24.
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