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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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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 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
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
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