Dekstrorfan

Dekstrorfan
(IUPAC) ime
	(+)-17-methyl- 9a,13a,14a-morphinan- 3-ol
Klinički podaci
Identifikatori
CAS broj	125-73-5
ATC kod	nije dodeljen
PubChem	5360697
Hemijski podaci
Formula	C17H23NO
Mol. masa	257.371 g/mol
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
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	OTC (SAD)

Dekstrorfan (DXO) je psihoaktivni lek iz morfinanske hemijske klase koji deluje kao antitusivni lek (supresant kašlja) i disocijativni halucinogen. On je dekstro-stereoizomer racemorfana, gde je leva-polovina levorfanol. Dekstrorfan se proizvodi O-demetilacijom dekstrometorfana CYP2D6-om. Dekstrorfan je NMDA antagonist i doprinosi riziku zloupotrebe dekstrometorfana.^[3]

Farmakologija

Nekompetitivni antagonist N-metil-D-aspartatnog receptora (NMDAR).^[4]^[5]^[6]
Agonist σ₁ i σ₂ sigma receptora.^[7]^[8]
Antagonist α₃β₄, α₄β₂, i α₇ nikotinskog acetilholinskog receptora.^[9]^[10]
Bloker L-tip naponom-kontrolisanog kalcijumskog kanala (LVGCC).^[6]^[11]

Literatura

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ 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.
↑ 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.
↑ 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.
↑ ^6,0 ^6,1 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. Arhivirano iz originala na datum 2011-07-18. Pristupljeno 2014-04-05.
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] 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.

[pmid2897648-4] 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.

[pmid2673498-5] 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.

[pmid18812887-6] 6,0 ^6,1 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. Arhivirano iz originala na datum 2011-07-18. Pristupljeno 2014-04-05.

[pmid9037429-7] 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.

[pmid10064839-8] 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.

[pmid15356218-9] 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.

[pmid10869398-10] 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.

[pmid11182165-11] 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.

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