Benzilylcholine mustard (''N''-2-chloroethyl-''N''-methyl 2-aminoethyl benzilate) is a modified version of

acetylcholine Acetylcholine (ACh) is an organic chemical that functions in the brain and body of many types of animals (including humans) as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Part ...

, so named because after cyclization in solution it forms an iminium derivative that is structurally similar to benzilylcholine. It is well known for being an

irreversible antagonist An irreversible antagonist is a type of antagonist that binds permanently to a receptor, either by forming a covalent bond to the active site, or alternatively just by binding so tightly that the rate of dissociation is effectively zero at rele ...

of the

muscarinic acetylcholine receptor Muscarinic acetylcholine receptors, or mAChRs, are acetylcholine receptors that form G protein-coupled receptor complexes in the cell membranes of certain neurons and other cells. They play several roles, including acting as the main end-rece ...

. It has been used in pharmacological experiments investigating the relationship between

receptor Receptor may refer to: * Sensory receptor, in physiology, any structure which, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and responds to a ...

occupancy and response. It was also one of the tools in characterization of the muscarinic acetylcholine receptor.

Mechanism

On the muscarinic acetylcholine receptor, benzilylcholine mustard acts as an

alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

at two sites, one site being the acetylcholine recognition site itself, and the other a site that stabilises the receptor in its inactive state.

Groups A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic iden ...

that can be alkylated in this way include

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

s, imines and

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

s.John C. Foreman, Torben Johansen, Alasdair J. Gibb (2009) ''Textbook of Receptor Pharmacology, Third Edition'', CRC Press
page 51
/ref>

References

{{Nitrogen mustards Alkylating agents Irreversible antagonists Muscarinic antagonists Nitrogen mustards Organochlorides Benzilate esters Chloroethyl compounds