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308123-60-6-18-Methoxycoronaridine 18-Methoxycoronaridine

18-Methoxycoronaridine

For research use only. Not for therapeutic Use.

  • CAT Number: I000051
  • CAS Number: 308123-60-6
  • Molecular Formula: C22H28N2O3
  • Molecular Weight: 368.477
  • Purity: ≥95%
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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.


Catalog Number I000051
CAS Number 308123-60-6
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
Purity ≥95%
Target Nicotinic α3β4 Antagonist
Solubility Soluble in DMSO
Storage -20°C
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
Reference

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.<br />
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.<br />
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.<br />
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.<br />
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.<br />
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. <br />
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.<br />
8: Silva EM, Cirne-Santos CC, Frugulhetti IC, Galv&#227;o-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.<br />
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.<br />
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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