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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

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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F J Ehlert et al.
Life sciences, 62(17-18), 1659-1664 (1998-05-19)
Irreversible ligands are useful tools for investigating the function of receptor subtypes in various physiological processes. The mechanism for alkylation involves the formation of a reversible receptor complex followed by a covalent reaction. The extent of receptor alkylation is determined
E A Thomas et al.
Molecular pharmacology, 44(1), 102-110 (1993-07-01)
A functional role for the M2 muscarinic receptor in smooth muscle contraction was investigated in isolated guinea pig ileum. Contractile responses to the muscarinic agonist oxotremorine-M (oxo-M) were measured in isolated ilea that had been pretreated with histamine (0.32 microM)
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
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
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
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