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| Names | |
|---|---|
| Preferred IUPAC name 2-[(2-Chloroethyl)methylamino]ethyl hydroxydi(phenyl)acetate | |
| Other names N-2-chloroethyl-N-methyl 2-aminoethyl benzilate, α-Hydroxy-α-phenylbenzeneacetic acid 2-[(2-chloroethyl)methylamino]ethyl ester | |
| Identifiers | |
3D model (JSmol) | |
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| UNII | |
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| Properties | |
| C19H22ClNO3 | |
| Molar mass | 347.836 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Benzilylcholine mustard (N-2-chloroethyl-N-methyl 2-aminoethyl benzilate) is a modified version ofacetylcholine, so named because after cyclization in solution it forms anaziridinium derivative that is structurally similar to benzilylcholine. It is well known for being anirreversible antagonist of themuscarinic acetylcholine receptor.[1] It has been used inpharmacological experiments investigating the relationship betweenreceptor occupancy and response. It was also one of the tools in characterization of the muscarinic acetylcholine receptor.[2]
On the muscarinic acetylcholine receptor, benzilylcholine mustard acts as analkylating agent at two sites, one site being the acetylcholine recognition site itself, and the other a site that stabilises the receptor in its inactive state.[3]Groups that can be alkylated in this way includethiols,alcohols,imines andcarboxylic acids.[4]
