18-Methoxycoronaridine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 527608

CAS#: 308123-60-6

Description: 18-Methoxycoronaridine, 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.


Price and Availability

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18-Methoxycoronaridine (18-MC) is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 527608
Name: 18-Methoxycoronaridine
CAS#: 308123-60-6
Chemical Formula: C22H28N2O3
Exact Mass: 368.21
Molecular Weight: 368.477
Elemental Analysis: C, 71.71; H, 7.66; N, 7.60; O, 13.03


Synonym: 18-Methoxycoronaridine; 18 Methoxycoronaridine; 18Methoxycoronaridine; 18-MC; 18 MC; 18MC

IUPAC/Chemical Name: 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

InChi Key: DTJQBBHYRQYDEG-SVBQBFEESA-N

InChi Code: 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

SMILES Code: COCC[C@H]1C[C@@H]2C[C@]3(C(OC)=O)[C@@]1([H])N(CCC4=C3NC5=CC=CC=C54)C2


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Eggan BL, McCallum SE. 18-Methoxycoronaridine acts in the medial habenula to attenuate behavioral and neurochemical sensitization to nicotine. Behav Brain Res. 2016 Jul 1;307:186-93. doi: 10.1016/j.bbr.2016.04.008. PubMed PMID: 27059333.

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. 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. PubMed PMID: 21324333.

4: 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. PubMed PMID: 21210086; PubMed Central PMCID: PMC3790315.

5: 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. PubMed PMID: 20457177; PubMed Central PMCID: PMC4575503.

6: Rezvani AH, Cauley MC, Slade S, Wells C, Glick S, Rose JE, Levin ED. Acute oral 18-methoxycoronaridine (18-MC) decreases both alcohol intake and IV nicotine self-administration in rats. Pharmacol Biochem Behav. 2016 Oct 29. pii: S0091-3057(16)30194-0. doi: 10.1016/j.pbb.2016.10.010. [Epub ahead of print] PubMed PMID: 27984095.

7: 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. PubMed PMID: 20951714; PubMed Central PMCID: PMC4575504.

8: 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. PubMed PMID: 19442876; PubMed Central PMCID: PMC2688769.

9: 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. PubMed PMID: 20303928; PubMed Central PMCID: PMC3787694.

10: Taraschenko OD, Rubbinaccio HY, Maisonneuve IM, Glick SD. 18-methoxycoronaridine: a potential new treatment for obesity in rats? Psychopharmacology (Berl). 2008 Dec;201(3):339-50. doi: 10.1007/s00213-008-1290-9. PubMed PMID: 18751969; PubMed Central PMCID: PMC3787601.

11: 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. PubMed PMID: 16626688.

12: 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.

13: Panchal V, Taraschenko OD, Maisonneuve IM, Glick SD. Attenuation of morphine withdrawal signs by intracerebral administration of 18-methoxycoronaridine. Eur J Pharmacol. 2005 Nov 21;525(1-3):98-104. PubMed PMID: 16289028.

14: Kuehne ME, He L, Jokiel PA, Pace CJ, Fleck MW, Maisonneuve IM, Glick SD, Bidlack JM. Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents. J Med Chem. 2003 Jun 19;46(13):2716-30. PubMed PMID: 12801235.

15: Zhang W, Ramamoorthy Y, Tyndale RF, Glick SD, Maisonneuve IM, Kuehne ME, Sellers EM. Metabolism of 18-methoxycoronaridine, an ibogaine analog, to 18-hydroxycoronaridine by genetically variable CYP2C19. Drug Metab Dispos. 2002 Jun;30(6):663-9. PubMed PMID: 12019193.

16: Delorenzi JC, Freire-de-Lima L, Gattass CR, de Andrade Costa D, He L, Kuehne ME, Saraiva EM. In vitro activities of iboga alkaloid congeners coronaridine and 18-methoxycoronaridine against Leishmania amazonensis. Antimicrob Agents Chemother. 2002 Jul;46(7):2111-5. PubMed PMID: 12069962; PubMed Central PMCID: PMC127312.

17: Alper K, Bai R, Liu N, Fowler SJ, Huang XP, Priori SG, Ruan Y. hERG Blockade by Iboga Alkaloids. Cardiovasc Toxicol. 2016 Jan;16(1):14-22. doi: 10.1007/s12012-015-9311-5. PubMed PMID: 25636206.

18: 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.

19: Szumlinski KK, McCafferty CA, Maisonneuve IM, Glick SD. Interactions between 18-methoxycoronaridine (18-MC) and cocaine: dissociation of behavioural and neurochemical sensitization. Brain Res. 2000 Jul 21;871(2):245-58. PubMed PMID: 10899291.

20: Szumlinski KK, Maisonneuve IM, Glick SD. The potential anti-addictive agent, 18-methoxycoronaridine, blocks the sensitized locomotor and dopamine responses produced by repeated morphine treatment. Brain Res. 2000 May 2;864(1):13-23. PubMed PMID: 10793182.