18-Methoxycoronaridine

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MedKoo CAT#: 527608

CAS#: 308123-60-6 (free base)

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.

Chemical Structure

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18-Methoxycoronaridine
CAS# 308123-60-6 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 527608
Name: 18-Methoxycoronaridine
CAS#: 308123-60-6 (free base)
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

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 266686-77-5 (HCl)   308123-60-6 (free base)  

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

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

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).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 368.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.