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C7041

Sigma-Aldrich

McN-A-343

≥98% (TLC)

Synonym(s):

(4-Hydroxy-2-butynyl)-1-trimethyl­ammonium-3-chloro­carbanilate chloride, 4-[N-(3-Chlorophenyl)carbamoyloxy]-2-­butynyl­trimethyl­ammonium chloride

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About This Item

Empirical Formula (Hill Notation):
C14H18Cl2N2O2
CAS Number:
55-45-8
Molecular Weight:
317.21
MDL number:
MFCD00055068
UNSPSC Code:
12352106
PubChem Substance ID:
24277827
NACRES:
NA.77

Quality Level

200

Assay

≥98% (TLC)

form

powder

color

off-white

solubility

H2O: soluble
ethanol: soluble

SMILES string

[Cl-].C[N+](C)(C)CC#CCOC(=O)Nc1cccc(Cl)c1

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

InChI key

CXFZFEJJLNLOTA-UHFFFAOYSA-N

Gene Information

human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)
rat ... Chrm1(25229)

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Biochem/physiol Actions

M1 muscarinic acetylcholine receptor agonist.

Preparation Note

Solutions may be stored for several days at 4 °C.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lauren T May et al.
Molecular pharmacology, 72(2), 463-476 (2007-05-26)
The M2 muscarinic acetylcholine receptor (mAChR) possesses at least one binding site for allosteric modulators that is dependent on the residues (172)EDGE(175), Tyr(177), and Thr(423). However, the contribution of these residues to actions of allosteric agonists, as opposed to modulators
Frederick J Mitchelson
Pharmacology & therapeutics, 135(2), 216-245 (2012-05-31)
The unusual pharmacology of McN-A-343 was first described by Roszowski in 1961. The agonist appeared to be a selective stimulant of muscarinic receptors in sympathetic ganglia, now known to be the muscarinic M₁ receptor subtype. However, subsequent research demonstrated that
Laura Oliveira et al.
Neuro-Signals, 14(5), 262-272 (2005-11-23)
At the rat motor endplate, pre-synaptic facilitatory adenosine A2A and muscarinic M1 receptors are mutually exclusive. We investigated whether these receptors share a common intracellular signalling pathway. Suppression of McN-A-343-induced M1 facilitation of [3H]ACh release was partially recovered when CGS21680C
Hinako Suga et al.
Molecular pharmacology, 78(4), 745-755 (2010-07-21)
Investigating how a test drug alters the reaction of a site-directed electrophile with a receptor is a powerful method for determining whether the drug acts competitively or allosterically, provided that the binding site of the electrophile is known. In this
Vindhya Nawaratne et al.
The Journal of biological chemistry, 285(25), 19012-19021 (2010-04-22)
The recently identified small molecule, 3-amino-5-chloro-6-methoxy-4-methylthieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (LY2033298), is the first selective allosteric modulator of the muscarinic acetylcholine receptors (mAChRs) that mediates both receptor activation and positive modulation of the endogenous agonist, acetylcholine (ACh), via the same allosteric site
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