18-Methoxycoronaridine


CAS No. : 308123-60-6

18-Methoxycoronaridine,308123-60-6
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:I000051
Synonyms:18-Methoxycoronaridine; 18 Methoxycoronaridine; 18Methoxycoronaridine; 18-MC; 18 MC; 18MC;methyl (6S,6aS,7R,9R)-7-(2-methoxyethyl)-7,8,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1/',2/':1,2]azepino[4,5-b]indole-6(6aH)-carboxylate
Molecular Formula:C22H28N2O3
Molecular Weight:368.477
Target:Nicotinic α3β4 Antagonist
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Appearance:Solid powder
Purity: > 98%
Cat No:I000051
Cas No:308123-60-6
Product-Name:18-Methoxycoronaridine
InChI:InChI=1S/C22H28N2O3/c1-26-10-8-15-11-14-12-22(21(25)27-2)19-17(7-9-24(13-14)20(15)22)16-5-3-4-6-18(16)23-19/h3-6,14-15,20,23H,7-13H2,1-2H3/t14-,15+,20+,22-/m1/s1
InChIKey:DTJQBBHYRQYDEG-SVBQBFEESA-N
SMILES:COCC[C@H]1C[C@@H]2C[C@]3(C(OC)=O)[C@@]1([H])N(CCC4=C3NC5=CC=CC=C54)C2
18-Methoxycoronaridine(cas 308123-60-6), also known as 18-MC, is a nicotinic α3β4 antagonist potentially for the treatment of cocaine abuse. 18-Methoxycoronaridine slows the rate of induction of behavioral sensitization to nicotine. The primary mechanism of action of 18-MC is believed to be the inhibition of α3β4 nicotinic acetylcholine receptors which are densely expressed in the medial habenula and interpeduncular nucleus. 18-Methoxycoronaridine has also been shown to attenuate sucrose reward, decrease sucrose intake and prevent the development of sucrose-induced obesity.
1: McCallum SE, Taraschenko OD, Hathaway ER, Vincent MY, Glick SD. Effects of 18-methoxycoronaridine on ghrelin-induced increases in sucrose intake and accumbal dopamine overflow in female rats. Psychopharmacology (Berl). 2011 May;215(2):247-56. doi: 10.1007/s00213-010-2132-0. Epub 2011 Jan 6. PubMed PMID: 21210086; PubMed Central PMCID: PMC3790315.
2: Polston JE, Pritchett CE, Sell EM, Glick SD. 18-Methoxycoronaridine blocks context-induced reinstatement following cocaine self-administration in rats. Pharmacol Biochem Behav. 2012 Nov;103(1):83-94. PubMed PMID: 22885280; PubMed Central PMCID: PMC3526685.
3: Taraschenko OD, Maisonneuve IM, Glick SD. Resistance of male Sprague-Dawley rats to sucrose-induced obesity: effects of 18-methoxycoronaridine. Physiol Behav. 2011 Feb 1;102(2):126-31. doi: 10.1016/j.physbeh.2010.10.010. Epub 2010 Oct 15. PubMed PMID: 20951714; PubMed Central PMCID: PMC4575504.
4: Arias HR, Rosenberg A, Feuerbach D, Targowska-Duda KM, Maciejewski R, Jozwiak K, Moaddel R, Glick SD, Wainer IW. Interaction of 18-methoxycoronaridine with nicotinic acetylcholine receptors in different conformational states. Biochim Biophys Acta. 2010 Jun;1798(6):1153-63. doi: 10.1016/j.bbamem.2010.03.013. Epub 2010 Mar 19. PubMed PMID: 20303928; PubMed Central PMCID: PMC3787694.
5: Taraschenko OD, Maisonneuve IM, Glick SD. Sex differences in high fat-induced obesity in rats: Effects of 18-methoxycoronaridine. Physiol Behav. 2011 Jun 1;103(3-4):308-14. doi: 10.1016/j.physbeh.2011.02.011. Epub 2011 Feb 12. PubMed PMID: 21324333.
6: Taraschenko OD, Maisonneuve IM, Glick SD. 18-Methoxycoronaridine, a potential anti-obesity agent, does not produce a conditioned taste aversion in rats. Pharmacol Biochem Behav. 2010 Sep;96(3):247-50. doi: 10.1016/j.pbb.2010.05.002. Epub 2010 May 10. PubMed PMID: 20457177; PubMed Central PMCID: PMC4575503.
7: McCallum SE, Glick SD. 18-Methoxycoronaridine blocks acquisition but enhances reinstatement of a cocaine place preference. Neurosci Lett. 2009 Jul 17;458(2):57-9. doi: 10.1016/j.neulet.2009.04.019. Epub 2009 Apr 11. PubMed PMID: 19442876; PubMed Central PMCID: PMC2688769.
8: Silva EM, Cirne-Santos CC, Frugulhetti IC, Galvão-Castro B, Saraiva EM, Kuehne ME, Bou-Habib DC. Anti-HIV-1 activity of the Iboga alkaloid congener 18-methoxycoronaridine. Planta Med. 2004 Sep;70(9):808-12. PubMed PMID: 15386189.
9: Mundey MK, Blaylock NA, Mason R, Glick SD, Maisonneuve IM, Wilson VG. Pharmacological comparison of the effect of ibogaine and 18-methoxycoronaridine on isolated smooth muscle from the rat and guinea-pig. Br J Pharmacol. 2000 Apr;129(8):1561-8. PubMed PMID: 10780959; PubMed Central PMCID: PMC1571996.
10: Glick SD, Ramirez RL, Livi JM, Maisonneuve IM. 18-Methoxycoronaridine acts in the medial habenula and/or interpeduncular nucleus to decrease morphine self-administration in rats. Eur J Pharmacol. 2006 May 10;537(1-3):94-8. Epub 2006 Mar 24. PubMed PMID: 16626688.
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