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M5644

Sigma-Aldrich

(±)-Methoxyverapamil hydrochloride

≥98%

Synonyme(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

Formule empirique (notation de Hill):
C28H40N2O5 · HCl
Numéro CAS:
16662-47-8
Poids moléculaire :
521.09
Numéro MDL:
MFCD00058000
Code UNSPSC :
12352200
ID de substance PubChem :
24277852
Nomenclature NACRES :
NA.77

Pureté

≥98%

Chaîne SMILES 

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

Clé InChI

OKCRIUNHEQSXFD-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

Blocks L-type Ca2+ channels

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Shigehiro Hayashi et al.
Acta pharmacologica Sinica, 31(1), 19-26 (2009-11-17)
To quantitatively assess the effect of lowering external Ca(2+) ([Ca(2+)](o)) on both endothelium-dependent and -independent relaxations in rabbit aorta. Isometric contractions and relaxations of isolated aortae were recorded. When assessing the effect of reduced [Ca(2+)](o) on relaxations, the normal [Ca(2+)](o)
Ho Jae Han et al.
Life sciences, 76(25), 2903-2919 (2005-04-12)
Embryonic stem (ES) cells are provided as a powerful tool for developmental biology and have been shown to respond to insulin. However, little is known about the effect of insulin on [Ca2+]i regulation in the ES cells, although many cellular
M A Bagni et al.
American journal of physiology. Cell physiology, 286(6), C1353-C1357 (2004-01-30)
At the end of the force transient elicited by a fast stretch applied to an activated frog muscle fiber, the force settles to a steady level exceeding the isometric level preceding the stretch. We showed previously that this excess of
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
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