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D142

Sigma-Aldrich

4-Diphenylacetoxy-N-(2-chloroethyl)piperidine hydrochloride

solid

Sinonimo/i:

4-DAMP mustard hydrochloride

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About This Item

Formula empirica (notazione di Hill):
C21H24ClNO2 · HCl
Numero CAS:
130817-71-9
Peso molecolare:
394.33
Numero MDL:
MFCD00153790
Codice UNSPSC:
12352200
ID PubChem:
24278403

Stato

solid

Colore

white

Solubilità

DMSO: soluble (Solutions must be freshly prepared.)
aqueous base: unstable

Stringa SMILE

Cl[H].ClCCN1CCC(CC1)OC(=O)C(c2ccccc2)c3ccccc3

Informazioni sul gene

human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)

Azioni biochim/fisiol

Irreversible muscarinic acetylcholine receptor antagonist with essentially equivalent affinity for M1, M3, M4, and M5 receptors and much lower affinity for M2 receptors.

Avvertenza

Hygroscopic

Codice della classe di stoccaggio

13 - Non Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
083K4619
100K4610

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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
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
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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