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:
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)
Regulatory Information
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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
Changqing Xu et al.
The European journal of neuroscience, 24(8), 2309-2313 (2006-11-01)
Neurons of the medial septum/diagonal band of Broca (MSDB) project to the hippocampus. Muscarinic cholinergic mechanisms within the MSDB are potent modulators of hippocampal functions; intraseptal scopolamine disrupts and intraseptal carbachol facilitates hippocampus-dependent learning and memory tasks, and the associated
N Watson et al.
European journal of pharmacology, 278(3), 195-201 (1995-05-24)
Muscarinic M2 receptors account for more than half the muscarinic receptor population in smooth muscles of a number of species and yet it is the smaller M3 receptor population that mediates contraction of many of these tissues. The role 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
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