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D142

Sigma-Aldrich

4-Diphenylacetoxy-N-(2-chloroethyl)piperidine hydrochloride

solid

Synonym(s):

4-DAMP mustard hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C21H24ClNO2 · HCl
CAS Number:
130817-71-9
Molecular Weight:
394.33
MDL number:
MFCD00153790
UNSPSC Code:
12352200
PubChem Substance ID:
24278403

form

solid

color

white

solubility

DMSO: soluble (Solutions must be freshly prepared.)
aqueous base: unstable

SMILES string

Cl[H].ClCCN1CCC(CC1)OC(=O)C(c2ccccc2)c3ccccc3

Gene Information

human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)

Biochem/physiol Actions

Irreversible muscarinic acetylcholine receptor antagonist with essentially equivalent affinity for M1, M3, M4, and M5 receptors and much lower affinity for M2 receptors.

Caution

Hygroscopic

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
100K4610
083K4619

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R M Eglen et al.
British journal of pharmacology, 109(4), 946-952 (1993-08-01)
1. The role of muscarinic M2 and M3 receptors in ileal smooth muscle has been evaluated by use of selective receptor alkylation. The alkylating agents, 4-diphenylacetoxy-N-(2-chloroethyl)-piperidine (4-DAMP mustard) was studied for effects against (+)-cis-dioxolane, at muscarinic M2 and M3 receptors
F J Ehlert
Life sciences, 58(22), 1971-1978 (1996-01-01)
The compound 4-DAMP mustard (N-2-chloroethyl-4-piperidinyl diphenylacetate) is a 2-chloroethylamine derivative of the selective muscarinic antagonist 4-DAMP (N,N-dimethyl-4-piperidinyl diphenylacetate). At neutral pH, 4-DAMP mustard cyclizes spontaneously into an oziridinium ion that binds covalently with muscarinic receptors. Analysis of the kinetics of
Johannes Bodenstein et al.
The Journal of pharmacology and experimental therapeutics, 314(2), 891-905 (2005-04-29)
Many irreversible antagonists have been shown to inactivate G protein-coupled receptors (GPCRs) and used to study agonists and spare receptors. Presumably, they bind to primary (agonist) binding sites on the GPCR, although noncompetitive mechanisms of antagonism have been demonstrated but
R S Ostrom et al.
The Journal of pharmacology and experimental therapeutics, 286(1), 234-242 (1998-07-10)
The ability of the M2 muscarinic receptor to inhibit the relaxant effects of forskolin and isoproterenol was investigated in bovine trachea. In most experiments, we measured contractile responses to oxotremorine-M in smooth muscle isolated from bovine trachea in which a
M T Griffin et al.
The Journal of pharmacology and experimental therapeutics, 266(1), 301-305 (1993-07-01)
4-DAMP mustard (N-2-chloroethyl)-4-piperidinyl diphenylacetate) has been shown to selectively and irreversibly inhibit muscarinic receptors. In an attempt to increase the rate of formation and peak concentration of the reactive intermediate, an analog [N-(2-bromoethyl)-4-piperidinyl diphenylacetate (4-DAMP bromo mustard)] was synthesized and
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