Benzilylcholine mustard

Benzilylcholine mustard
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
CAS Number	5746-42-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	4955866 ;
PubChem CID	6453495;
UNII	3KYG5U8PYV ;
CompTox Dashboard (EPA)	DTXSID50206070 ;
	InChI InChI=1S/C19H22ClNO3/c1-21(13-12-20)14-15-24-18(22)19(23,16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,23H,12-15H2,1H3 Key: QMMKHOXGBKDMKE-UHFFFAOYSA-N ;
	SMILES CN(CCOC(=O)C(C1=CC=CC=C1)(C2=CC=CC=C2)O)CCCl;
Properties
Chemical formula	C19H22ClNO3
Molar mass	347.836 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

References

^ Gill, E.W.; Rang, H.P. (July 1966) "An Alkylating Derivative of Benzilylcholine with Specific and Long-Lasting Parasympatholytic Activity", Molecular Pharmacology, vol.2 no.4 284-297
^ Gupta, Surendra K.; Moran, John F.; Triggle, David F. (November 1976) "Mechanism of Action of Benzilylcholine Mustard at the Muscarinic Receptor", Molecular Pharmacology, vol.12 no.6 1019-1026
^ Gupta, Moran, Triggle (1974)
^ John C. Foreman, Torben Johansen, Alasdair J. Gibb (2009) Textbook of Receptor Pharmacology, Third Edition, CRC Press, page 51

[1] Gill, E.W.; Rang, H.P. (July 1966) "An Alkylating Derivative of Benzilylcholine with Specific and Long-Lasting Parasympatholytic Activity", Molecular Pharmacology, vol.2 no.4 284-297

[2] Gupta, Surendra K.; Moran, John F.; Triggle, David F. (November 1976) "Mechanism of Action of Benzilylcholine Mustard at the Muscarinic Receptor", Molecular Pharmacology, vol.12 no.6 1019-1026

[3] Gupta, Moran, Triggle (1974)

[4] John C. Foreman, Torben Johansen, Alasdair J. Gibb (2009) Textbook of Receptor Pharmacology, Third Edition, CRC Press, page 51

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v t e Nitrogen mustards
Vesicants	HN1 HN2 HN3 TL-301 TL-481 TL-512 TL-513 TL-695 TL-995
Antineoplastic agents	Aniline mustard Bendamustine Chlorambucil Cyclophosphamide Mannomustine Melphalan Mustamine Phenylenediamine mustard Quinacrine mustard Spiromustine
Neurotoxins	Acetylcholine mustard Acetylethylcholine mustard Benzilylcholine mustard Choline mustard Decamethonium mustard DMEA DSP-4 Ethylcholine mustard Hemicholinium mustard Propylbenzilylcholine mustard
Other	Dibenamine Phenoxybenzamine SY-28

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
CAS Number	5746-42-9^Y
3D model (JSmol)	Interactive image
ChemSpider	4955866^Y
PubChem CID	6453495
UNII	3KYG5U8PYV^Y
CompTox Dashboard (EPA)	DTXSID50206070
InChI InChI=1S/C19H22ClNO3/c1-21(13-12-20)14-15-24-18(22)19(23,16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,23H,12-15H2,1H3^Y Key: QMMKHOXGBKDMKE-UHFFFAOYSA-N^Y
SMILES CN(CCOC(=O)C(C1=CC=CC=C1)(C2=CC=CC=C2)O)CCCl
Properties
Chemical formula	C₁₉H₂₂ClNO₃
Molar mass	347.836 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references