Benzilylcholine mustard (N-2-chloroethyl-N-methyl 2-aminoethyl benzilate) is a modified version of
acetylcholine, so named because after cyclization in solution it forms an
aziridinium derivative that is structurally similar to benzilylcholine. It is well known for being an
irreversible antagonist of the
muscarinic acetylcholine receptor.[1] It has been used in
pharmacological experiments investigating the relationship between
receptor occupancy and response. It was also one of the tools in characterization of the muscarinic acetylcholine receptor.[2]
Mechanism
On the muscarinic acetylcholine receptor, benzilylcholine mustard acts as an
alkylating 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 include
thiols,
alcohols,
imines and
carboxylic acids.[4]
Benzilylcholine mustard (N-2-chloroethyl-N-methyl 2-aminoethyl benzilate) is a modified version of
acetylcholine, so named because after cyclization in solution it forms an
aziridinium derivative that is structurally similar to benzilylcholine. It is well known for being an
irreversible antagonist of the
muscarinic acetylcholine receptor.[1] It has been used in
pharmacological experiments investigating the relationship between
receptor occupancy and response. It was also one of the tools in characterization of the muscarinic acetylcholine receptor.[2]
Mechanism
On the muscarinic acetylcholine receptor, benzilylcholine mustard acts as an
alkylating 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 include
thiols,
alcohols,
imines and
carboxylic acids.[4]