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M5644

Sigma-Aldrich

(±)-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
MDL number:
MFCD00058000
UNSPSC Code:
12352200
PubChem Substance ID:
24277852
NACRES:
NA.77

Quality Level

200

Assay

≥98%

SMILES string

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

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

InChI key

OKCRIUNHEQSXFD-UHFFFAOYSA-N

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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