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Merck
CN

M5644

(±)-Methoxyverapamil hydrochloride

≥98%

Synonym(s):

(±)-α-[3-[(2-(3,4-Dimethoxyphenyl)ethyl)methylamino]propyl]-3,4,5-trimethoxy-α-(1-methylethyl)benzeneacetonitrile hydrochloride, D 600, Gallopamil

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About This Item

Empirical Formula (Hill Notation):
C28H40N2O5 · HCl
CAS Number:
16662-47-8
Molecular Weight:
521.09
NACRES:
NA.77
PubChem Substance ID:
24277852
UNSPSC Code:
12352200
MDL number:
MFCD00058000

Key Documents

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InChI

1S/C28H40N2O5.ClH/c1-20(2)28(19-29,22-17-25(33-6)27(35-8)26(18-22)34-7)13-9-14-30(3)15-12-21-10-11-23(31-4)24(16-21)32-5;/h10-11,16-18,20H,9,12-15H2,1-8H3;1H

SMILES string

Cl[H].COc1ccc(CCN(C)CCCC(C#N)(C(C)C)c2cc(OC)c(OC)c(OC)c2)cc1OC

InChI key

OKCRIUNHEQSXFD-UHFFFAOYSA-N

assay

≥98%

Quality Level

200

General description

Methoxyverapamil is a calmodulin antagonist. It controls flagellar glycoprotein redistribution by modulating calcium signalling. Methoxyverapamil impacts the effect of intracellular calcium levels and affects the sperm capacitation function.

Application

(±)-Methoxyverapamil hydrochloride has been used:
  • as calcium channel antagonist in Schistosoma mansoni parasite
  • as calcium entry blocker in cultured macrophages
  • in the inhibition of L-type voltage gated Ca2+-channels

Biochem/physiol Actions

Blocks L-type Ca2+ channels

Storage Class

11 - 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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Certificates of Analysis (COA)

Lot/Batch Number
038F0122

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Anamika Awasthi et al.
Bioorganic & medicinal chemistry letters, 15(24), 5412-5415 (2005-10-11)
Ab initio Hartree-Fock calculations have been performed at the 6-31G level to study the pharmacophoric features of verapamil. Both the unprotonated and the protonated forms of verapamil have been studied. The study predicts that the drug enters the body in
Iliyana D Stefanova et al.
Molecular nutrition & food research, 51(4), 468-472 (2007-03-16)
Melanoidins obtained from L-arginine and D-glucose (MW > 3500 Da) were tested for their ability to influence the contractility of gastric smooth muscles. A study within the range 0.1-10 mg/mL revealed that at low concentrations, the melanoidins provoked concentration-dependent contraction
D N Serban et al.
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 108(2), 445-451 (2005-02-04)
Membrane potential (MP) is essential in smooth muscle (SM) contractile activity, mainly by its effect upon L-type Ca2+ channels. We simultaneously recorded SM isometric tension and MP in de-endothelised rat aorta rings and examined their submaximal activation by K+, norepinephrine
Inhibition of cholesteryl ester deposition in macrophages by calcium entry blockers: an effect dissociable from calcium entry blockade
Daugherty A, et al.
British Journal of Pharmacology, 91(1), 113-118 (1987)
Beatrice Pöschel et al.
Neuropharmacology, 52(1), 46-54 (2006-08-11)
Hippocampal long-term depression (LTD) comprises a persistent reduction of synaptic strength that is typically induced by low frequency stimulation (LFS). Although LTD has been described for the dentate gyrus in vitro, this phenomenon in the dentate gyrus of the intact
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Product Information Sheet - M5644

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