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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

Certificates of Analysis (COA)

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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
M G Hendriks et al.
Blood pressure, 2(4), 332-338 (1993-12-01)
Possible hypertension-related alterations in the nature- and receptor reserve of the muscarinic (M) receptors mediating endothelium-dependent vasodilation remain to be elucidated. Therefore we used 4-diphenylacetoxy-N-(2-chloroethyl)-piperidine (4-DAMPmustard), an irreversible M3-receptor antagonist, to estimate the receptor reserve for the methacholine (MCh)-induced endothelium-dependent
A S Braverman et al.
Journal of receptor and signal transduction research, 19(5), 819-833 (1999-06-01)
Our previous data indicate that M3 muscarinic receptors mediate carbachol induced bladder contractions. The data presented here were obtained by selective alkylation of M3 receptors with 4-DAMP mustard and suggest that the M2 receptor subtype may be involved in inhibition
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
E A Thomas et al.
Molecular pharmacology, 41(4), 718-726 (1992-04-01)
A 2-chloroethylamine derivative [N-(2-chloroethyl)-4-piperidinyl diphenylacetate (4-DAMP mustard)] of the selective muscarinic antagonist N,N-dimethyl-4-piperidinyl diphenylacetate (4-DAMP) was synthesized, and its conversion to an aziridinium ion and interaction with muscarinic receptors was investigated. When dissolved in aqueous solution at pH 7.4 and
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