dextrorphan

Dextrorphan
Systematic (IUPAC) name
	(+)-17-methyl-9a,13a,14a-morphinan-3-ol
Legal status
Legal status	US: Unscheduled;
Identifiers
CAS Number	125-73-5
ATC code	none
PubChem	CID 5360697
ChemSpider	10489895
UNII	04B7QNO9WS
ChEMBL	CHEMBL341216
Chemical data
Formula	C17H23NO
Molar mass	257.371 g/mol
	SMILES OC1=CC2=C(C[C@@H]3N(CC[C@@]42CCCC[C@H]34)C)C=C1 ;
	InChI InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1 ; Key:JAQUASYNZVUNQP-PVAVHDDUSA-N ;
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デキストロルファン

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/07/02 18:12:19」(JST)

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[Wiki en表示]

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]

Legality

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

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.
^ ^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.
^ 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.

UpToDate Contents

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1. デキストロメトルファン中毒：疫学、薬学および臨床的特徴 dextromethorphan poisoning epidemiology pharmacology and clinical features

English Journal

Repeated administration of berberine inhibits cytochromes P450 in humans.

Guo Y, Chen Y, Tan ZR, Klaassen CD, Zhou HH.SourcePharmacogenetics Research Institute, Institute of Clinical Pharmacology, Central South University, XiangYa School of Medicine, 110 Xiang-Ya Road, Changsha, Hunan, 410078, People's Republic of China, yguo2@kumc.edu.
European journal of clinical pharmacology.Eur J Clin Pharmacol.2012 Feb;68(2):213-7. Epub 2011 Aug 26.
PURPOSE: Berberine is a plant alkaloid that is widely used to treat gastrointestinal infections, diabetes, hypertension, and hypercholesterolemia. Many studies have reported interactions between berberine-containing products and cytochromes P450 (CYPs), but little is known about whether berberine al
PMID 21870106

Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole.

Lutz JD, Isoherranen N.SourceSchool of Pharmacy, Department of Pharmaceutics, University of Washington, Box 357610, H272 Health Science Building, Seattle, WA 98195-7610. ni2@u.washington.edu.
Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2012 Jan;40(1):159-68. Epub 2011 Oct 18.
Metabolites can have pharmacological or toxicological effects, inhibit metabolic enzymes, and be used as probes of drug-drug interactions or specific cytochrome P450 (P450) phenotypes. Thus, better understanding and prediction methods are needed to characterize metabolite exposures in vivo. This stu
PMID 22010218

Effect of Ginkgo biloba special extract EGb 761® on human cytochrome P450 activity: a cocktail interaction study in healthy volunteers.

Zadoyan G, Rokitta D, Klement S, Dienel A, Hoerr R, Gramatté T, Fuhr U.SourceDepartment of Pharmacology Clinical Pharmacology Unit, University of Cologne, Gleueler Str. 24, 50931, Cologne, Germany.
European journal of clinical pharmacology.Eur J Clin Pharmacol.2011 Dec 21. [Epub ahead of print]
PURPOSE: We assessed the human in vivo metabolic drug interaction profile of Ginkgo biloba extract EGb 761® with respect to the activities of major cytochrome P450 (CYP) enzymes.METHODS: A single-center, open-label, randomized, three-fold crossover, cocktail phenotyping design was applied. In rando
PMID 22189672

Japanese Journal

Human Cytosolic Sulfotransferase SULT1A3 Mediates the Sulfation of Dextrorphan

Ｂｉｏｌｏｇｉｃａｌ　＆　Ｐｈａｒｍａｃｅｕｔｉｃａｌ　Ｂｕｌｌｅｔｉｎ 39(9), 1432-1436, 2016
NAID 130005262319

Simultaneous LC-MS/MS Analysis of the Plasma Concentrations of a Cocktail of 5 Cytochrome P450 Substrate Drugs and Their Metabolites

Biological and Pharmaceutical Bulletin 37(1), 18-25, 2014
NAID 130003382092

Simultaneous Determination of Dextromethorphan and Its Metabolite Dextrorphan in Plasma Samples Using Second-order Calibration Coupled with Excitation-Emission Matrix Fluorescence

Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 27(6), 663-666, 2011-06-10
NAID 10028289463

Related Pictures

[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.

[pmid2897648-2] 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.

[pmid2673498-3] 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.

[pmid18812887-4] 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.

[:0-5] 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.

[pmid9037429-6] 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.

[pmid10064839-7] 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 3930996. PMID 24393077.

[pmid15356218-9] 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.

[pmid10869398-10] 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.

[pmid11182165-11] 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.

[urlDextrorphan_Legality-13] DEA. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). Retrieved 2010-09-24.

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