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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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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
Calcium influx regulates antibody-induced glycoprotein movements within the Chlamydomonas flagellar membrane
Bloodgood RA and Salomonsky NL
Journal of Cell Science, 96(1), 27-33 (1990)
Hidetada Matsuoka et al.
American journal of physiology. Cell physiology, 296(4), C889-C899 (2009-01-30)
It has been suggested that store-operated Ca(2+) entry (SOC) facilitates catecholamine secretion and synthesis in bovine adrenal medullary (AM) cells. However, there has been no experimental result clearly showing that cation channel activity is enhanced by store Ca(2+) depletion. Thus
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)
Wayne M Mullett et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 801(2), 297-306 (2004-01-31)
A new molecularly imprinted polymer (MIP) material was synthesized selective for verapamil and utilized for on-line metabolic screening of this common calcium antagonist in biological samples. Since some metabolites of verapamil have also shown pharmacological properties, a selective and sensitive
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