Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H18ClN2O2 |
| Molecular Weight | 281.758 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 1 |
SHOW SMILES / InChI
SMILES
C[N+](C)(C)CC#CCOC(=O)NC1=CC=CC(Cl)=C1
InChI
InChIKey=DDKOMKXCUXCQBS-UHFFFAOYSA-O
InChI=1S/C14H17ClN2O2/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/p+1
4-(M-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium (McN-A-343) is a selective muscarinic M1 receptors agonist, which leads to its widespread use as an aid to distinguish responses mediated through M₁ receptors from those utilizing M₂ or M₃ muscarinic receptor subtypes, especially in the CNS. McN-A-343 has a number of non-muscarinic actions. These include activation of some types of nicotinic acetylcholine receptors, antagonism of serotonin 5-HT₃ and 5-HT₄ receptor subtypes, inhibition of the uptake mechanism and a local anesthetic action.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Functional determination of McN-A-343 affinity for M1 muscarinic receptors. | 1990 Apr |
|
| A novel mechanism of G protein-coupled receptor functional selectivity. Muscarinic partial agonist McN-A-343 as a bitopic orthosteric/allosteric ligand. | 2008 Oct 24 |
|
| Investigating the interaction of McN-A-343 with the M2 muscarinic receptor using its nitrogen mustard derivative. | 2010 Apr 1 |
|
| The pharmacology of McN-A-343. | 2012 Aug |
Patents
Sample Use Guides
The selective M1-receptor agonist McN-A-343 ((4-(M-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium ) (100μM) induced a current similar to the CCh-activated current in sinus rhythm atrial cardiomyocytes pretreated with pertussis toxin to inhibit M2-receptor-mediated Gi-protein signaling, which was abolished by MT-7.
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DTXSID70226997
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7614-29-1
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4022
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SUBSTANCE RECORD
