D142
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:
Molecular Weight:
394.33
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
Product Name
4-Diphenylacetoxy-N-(2-chloroethyl)piperidine hydrochloride, solid
SMILES string
Cl[H].ClCCN1CCC(CC1)OC(=O)C(c2ccccc2)c3ccccc3
form
solid
color
white
solubility
DMSO: soluble (Solutions must be freshly prepared.)
aqueous base: unstable
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.
Disclaimer
Hygroscopic
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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
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
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