D142
4-Diphenylacetoxy-N-(2-chloroethyl)piperidine hydrochloride
solid
Synonym(e):
4-DAMP mustard hydrochloride
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Empirische Formel (Hill-System):
C21H24ClNO2 · HCl
CAS-Nummer:
Molekulargewicht:
394.33
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
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Unterstützung erhaltenform
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.
Disclaimer
Hygroscopic
Lagerklasse
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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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
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
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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