McN-A-343
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MedKoo CAT#: 462190

CAS#: 55-45-8 (chloride)

Description: McN-A-343, also known as McNA343, is a muscarinic agonist, reduces inflammation and oxidative stress in an experimental model of ulcerative colitis. McN-A-343 increases renal sympathetic nerve activity and blood pressure by a muscarinic and a non-muscarinic mechanism in the rat. McN-A-343 and its nitrogen mustard derivative interact competitively with ACh and N-methylscopolamine at the orthosteric site on the M(1) muscarinic receptor.

Chemical Structure

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McN-A-343
CAS# 55-45-8 (chloride)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 462190
Name: McN-A-343
CAS#: 55-45-8 (chloride)
Chemical Formula: C14H18Cl2N2O2
Exact Mass: 316.07
Molecular Weight: 317.210
Elemental Analysis: C, 53.01; H, 5.72; Cl, 22.35; N, 8.83; O, 10.09

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Related CAS #: 55-45-8 (chloride)   7614-29-1 (cation),  

Synonym: A 343; McN 343; McN-343; McN343; McN-A 343-11; McN-A-343; McN-A 343; McN-A343;

IUPAC/Chemical Name: 4-[[[(3-chlorophenyl)amino]carbonyl]oxy]-N,N,N-trimethyl-2-butyn-1-aminium, monochloride

InChi Key: CXFZFEJJLNLOTA-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H17ClN2O2.ClH/c1-17(2,3)9-4-5-10-19-14(18)16-13-8-6-7-12(15)11-13;/h6-8,11H,9-10H2,1-3H3;1H

SMILES Code: C[N+](C)(C)CC#CCOC(NC1=CC=CC(Cl)=C1)=O.[Cl-]

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: >3 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: McN-A-343, also known as McNA343, is a muscarinic agonist.
In vitro activity: TBD
In vivo activity: After the induction of 6% acetic acid colitis, mice were treated with McN-A-343 0.5, 1.0, and 1.5 mg/kg or dexamethasone (DEXA, 2.0 mg/kg) or pirenzepine (PIR, 10 mg/kg; M1 mAChR antagonist). Treatment with McN-A-343 at a concentration of 1.5 mg/kg showed a significant reduction in intestinal damage as well as a decrease in wet weight, MPO activity, pro-inflammatory cytokine concentration, markers of oxidative stress and expression of inflammatory mediators. Reference: Life Sci. 2021 May 1;272:119194. https://pubmed.ncbi.nlm.nih.gov/33609541/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 15.0 47.29
DMSO 25.0 78.81
Ethanol 15.0 47.29
PBS (pH 7.2) 10.0 31.52

Preparing Stock Solutions

The following data is based on the product molecular weight 317.21 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: 1. Magalhães DA, Batista JA, Sousa SG, Ferreira JDS, da Rocha Rodrigues L, Pereira CMC, do Nascimento Lima JV, de Albuquerque IF, Bezerra NLSD, Monteiro CEDS, Franco AX, da Costa Filho HB, Ferreira FCS, Havt A, Di Lenardo D, Vasconcelos DFP, de Oliveira JS, Soares PMG, Barbosa ALDR. McN-A-343, a muscarinic agonist, reduces inflammation and oxidative stress in an experimental model of ulcerative colitis. Life Sci. 2021 May 1;272:119194. doi: 10.1016/j.lfs.2021.119194. Epub 2021 Feb 18. PMID: 33609541. 2. Migita K, Nishimura A, Eto F, Koga K, Matsumoto T, Terada K, Hara S, Honda K. Muscarinic M1 receptors stimulated by intracerebroventricular administration of McN-A-343 reduces the nerve injury-induced mechanical hypersensitivity via GABAB receptors rather than GABAA receptors in mice. J Pharmacol Sci. 2020 Feb;142(2):50-59. doi: 10.1016/j.jphs.2019.06.010. Epub 2019 Jun 28. PMID: 31818640.
In vitro protocol: TBD
In vivo protocol: 1. Magalhães DA, Batista JA, Sousa SG, Ferreira JDS, da Rocha Rodrigues L, Pereira CMC, do Nascimento Lima JV, de Albuquerque IF, Bezerra NLSD, Monteiro CEDS, Franco AX, da Costa Filho HB, Ferreira FCS, Havt A, Di Lenardo D, Vasconcelos DFP, de Oliveira JS, Soares PMG, Barbosa ALDR. McN-A-343, a muscarinic agonist, reduces inflammation and oxidative stress in an experimental model of ulcerative colitis. Life Sci. 2021 May 1;272:119194. doi: 10.1016/j.lfs.2021.119194. Epub 2021 Feb 18. PMID: 33609541. 2. Migita K, Nishimura A, Eto F, Koga K, Matsumoto T, Terada K, Hara S, Honda K. Muscarinic M1 receptors stimulated by intracerebroventricular administration of McN-A-343 reduces the nerve injury-induced mechanical hypersensitivity via GABAB receptors rather than GABAA receptors in mice. J Pharmacol Sci. 2020 Feb;142(2):50-59. doi: 10.1016/j.jphs.2019.06.010. Epub 2019 Jun 28. PMID: 31818640.

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1: Magalhães DA, Batista JA, Sousa SG, Ferreira JDS, da Rocha Rodrigues L, Pereira CMC, do Nascimento Lima JV, de Albuquerque IF, Bezerra NLSD, Monteiro CEDS, Franco AX, da Costa Filho HB, Ferreira FCS, Havt A, Di Lenardo D, Vasconcelos DFP, de Oliveira JS, Soares PMG, Barbosa ALDR. McN-A-343, a muscarinic agonist, reduces inflammation and oxidative stress in an experimental model of ulcerative colitis. Life Sci. 2021 May 1;272:119194. doi: 10.1016/j.lfs.2021.119194. Epub 2021 Feb 18. PMID: 33609541.


2: Migita K, Nishimura A, Eto F, Koga K, Matsumoto T, Terada K, Hara S, Honda K. Muscarinic M1 receptors stimulated by intracerebroventricular administration of McN-A-343 reduces the nerve injury-induced mechanical hypersensitivity via GABAB receptors rather than GABAA receptors in mice. J Pharmacol Sci. 2020 Feb;142(2):50-59. doi: 10.1016/j.jphs.2019.06.010. Epub 2019 Jun 28. PMID: 31818640.


3: Suga H, Ehlert FJ. Effects of asparagine mutagenesis of conserved aspartic acids in helix 2 (D2.50) and 3 (D3.32) of M1-M4 muscarinic receptors on the irreversible binding of nitrogen mustard analogs of acetylcholine and McN-A-343. Biochemistry. 2013 Jul 23;52(29):4914-28. doi: 10.1021/bi4003698. Epub 2013 Jul 15. PMID: 23826889; PMCID: PMC3855626.


4: Mitchelson FJ. The pharmacology of McN-A-343. Pharmacol Ther. 2012 Aug;135(2):216-45. doi: 10.1016/j.pharmthera.2012.05.008. Epub 2012 May 27. PMID: 22643681.


5: Suga H, Sawyer GW, Ehlert FJ. Mutagenesis of nucleophilic residues near the orthosteric binding pocket of M1 and M2 muscarinic receptors: effect on the binding of nitrogen mustard analogs of acetylcholine and McN-A-343. Mol Pharmacol. 2010 Oct;78(4):745-55. doi: 10.1124/mol.110.065367. Epub 2010 Jul 19. PMID: 20643905; PMCID: PMC2981396.


6: Figueroa KW, Suga H, Ehlert FJ. Investigating the interaction of McN-A-343 with the M muscarinic receptor using its nitrogen mustard derivative and ACh mustard. Br J Pharmacol. 2010 Jul;160(6):1534-49. doi: 10.1111/j.1476-5381.2010.00810.x. PMID: 20590642; PMCID: PMC2938823.


7: Suga H, Ehlert FJ. Investigating the interaction of McN-A-343 with the M2 muscarinic receptor using its nitrogen mustard derivative. Biochem Pharmacol. 2010 Apr 1;79(7):1025-35. doi: 10.1016/j.bcp.2009.11.005. Epub 2009 Nov 12. PMID: 19913516; PMCID: PMC2815195.


8: Honda K, Horikawa K, Ando S, Koga K, Kawata S, Migita K, Takano Y. The spinal muscarinic M(1) receptors and GABA(A) receptors contribute to the McN-A-343-induced antinociceptive effects during thermal stimulation of mice. J Pharmacol Sci. 2008 Dec;108(4):472-9. doi: 10.1254/jphs.08226fp. Epub 2008 Dec 5. PMID: 19057125.


9: Valant C, Gregory KJ, Hall NE, Scammells PJ, Lew MJ, Sexton PM, Christopoulos A. A novel mechanism of G protein-coupled receptor functional selectivity. Muscarinic partial agonist McN-A-343 as a bitopic orthosteric/allosteric ligand. J Biol Chem. 2008 Oct 24;283(43):29312-21. doi: 10.1074/jbc.M803801200. Epub 2008 Aug 22. PMID: 18723515; PMCID: PMC2662018.


10: Davies RH, Scholes HE, Virdi S, Broadley KJ. Inhibition of field stimulation-induced contractions of rabbit vas deferens by muscarinic receptor agonists: selectivity of McN-A-343 for M1 receptors. J Pharm Pharmacol. 2001 Apr;53(4):487-96. doi: 10.1211/0022357011775785. PMID: 11341365.


11: Tumiatti V, Angeli P, Andrisano V, Bolognesi ML, Cavalli A, Marucci G, Minarini A, Recanatini M, Rosini M, Melchiorre C. [4-[[N-(3-chlorophenyl)carbamoyl]oxy]-2-butynyl]-trimethylammonium (McN-A-343)-related compounds. Effect of the butynyl chain inclusion into an aromatic unit on the potency for muscarinic receptors. Bioorg Med Chem. 2000 Apr;8(4):681-9. doi: 10.1016/s0968-0896(99)00309-0. PMID: 10819156.


12: Shen JB, Jiang B, Pappano AJ. Lack of effect of McN-A-343 on membrane current and contraction in guinea pig ventricular myocytes. J Pharmacol Exp Ther. 1999 Aug;290(2):641-8. PMID: 10411573.


13: Christopoulos A, Mitchelson F. Pharmacological analysis of the mode of interaction of McN-A-343 at atrial muscarinic M2 receptors. Eur J Pharmacol. 1997 Nov 27;339(2-3):153-6. doi: 10.1016/s0014-2999(97)01379-4. PMID: 9473129.


14: Hishinuma S, Hongo I, Matsumoto Y, Narita F, Kurokawa M. Contrasting effects of carbachol, McN-A-343 and AHR-602 on Ca(2+)-mobilization and Ca(2+)-influx pathways in taenia caeci. Br J Pharmacol. 1997 Nov;122(6):985-92. doi: 10.1038/sj.bjp.0701467. PMID: 9401759; PMCID: PMC1565030.


15: Martin JR. McN-A-343 increases renal sympathetic nerve activity and blood pressure by a muscarinic and a non-muscarinic mechanism in the rat. J Auton Pharmacol. 1996 Oct;16(5):281-92. doi: 10.1111/j.1474-8673.1996.tb00362.x. PMID: 9023672.


16: Martin JR. Pressor effect of the putative M1 muscarinic receptor agonist MCN-A-343 in the conscious rat. Life Sci. 1996;59(22):1839-52. doi: 10.1016/s0024-3205(96)00531-0. PMID: 8950281.


17: Koss MC, Wally JR. Analysis of miosis produced by McN-A-343 in anesthetized cats. J Ocul Pharmacol Ther. 1995 Fall;11(3):389-99. doi: 10.1089/jop.1995.11.389. PMID: 8590271.


18: Iwabuchi Y, Masuhara T. Sialogogic activities of SNI-2011 compared with those of pilocarpine and McN-A-343 in rat salivary glands: identification of a potential therapeutic agent for treatment of Sjörgen's syndrome. Gen Pharmacol. 1994 Jan;25(1):123-9. doi: 10.1016/0306-3623(94)90021-3. PMID: 7517901.


19: Elnatan A, Mitchelson F. The interaction of McN-A-343 with muscarine receptors in cardiac and smooth muscle. Biochem Pharmacol. 1993 Sep 14;46(6):993-1003. doi: 10.1016/0006-2952(93)90663-h. PMID: 7692853.


20: Mathes C, Wang SS, Vargas HM, Thompson SH. Intracellular calcium release in N1E-115 neuroblastoma cells is mediated by the M1 muscarinic receptor subtype and is antagonized by McN-A-343. Brain Res. 1992 Jul 10;585(1-2):307-10. doi: 10.1016/0006-8993(92)91225-4. PMID: 1380873.