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V4629

Sigma-Aldrich

(±)-Verapamil hydrochloride

≥99% (titration), powder, α1-adrenoceptor antagonist

Synonym(s):

5-[N-(3,4-Dimethoxyphenylethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride

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About This Item

Linear Formula:
(CH3O)2C6H3CH2CH2N(CH3)(CH2)3C[C6H3(OCH3)2][CH(CH3)2]CN · HCl
CAS Number:
152-11-4
Molecular Weight:
491.06
Beilstein/REAXYS Number:
3647093
EC Number:
205-800-5
MDL number:
MFCD00055208
UNSPSC Code:
12352200
PubChem Substance ID:
24277881
NACRES:
NA.77

product name

(±)-Verapamil hydrochloride, ≥99% (titration), powder

assay

≥99% (titration)

form

powder

color

white

mp

142 °C (dec.) (lit.)

solubility

methanol: 50 mg/mL
ethanol: soluble

SMILES string

Cl.COc1ccc(CCN(C)CCCC(C#N)(C(C)C)c2ccc(OC)c(OC)c2)cc1OC

InChI

1S/C27H38N2O4.ClH/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6;/h9-12,17-18,20H,8,13-16H2,1-7H3;1H

InChI key

DOQPXTMNIUCOSY-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , CACNA1C(775) , CACNA1D(776) , CACNA1F(778) , CACNA1S(779)

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Application

Verapamil hydrochloride has been used:
  • to inhibit calcium oscillation in fertilized oocyte
  • to block calcium channel, thereby blocking the action of IL-1β (interleukin-1β), resulting in membrane depolarization
  • to investigate the effect of verapamil on cytotoxicity of 1,3-dilinoleoylglycerol (DLG)

Biochem/physiol Actions

α1-adrenoceptor antagonist; L-type calcium channel blocker. Blocks L-type Ca2+ channels in smooth and cardiac muscle, induces apoptosis of human primary and metastatic colon adenocarcinoma cells in vitro. Drug resistance reversal agent acting on Pgp, e.g. decrease renal tubule elimination of digoxin. Increases basal ATPase activity of Pgp. Substrate of Cyp3A4 and CYP2C6.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Calcium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

hcodes

H301,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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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O V Kolomytkin et al.
The American journal of physiology, 276(1 Pt 1), C9-C15 (1999-01-14)
The possibility that membrane depolarization of synovial fibroblasts caused by interleukin-1beta (IL-1beta) was mediated by protein kinase C (PKC) and Ca2+ influx was studied using inhibitor and activator analysis. The effect of IL-1beta was blocked by bisindolylmaleimide I, an inhibitor
Abdalla Elbialy et al.
Biology, 9(6) (2020-06-11)
In our previous publication, it was shown that growth hormone (GH) excess in acromegaly affects the cell integrity of somatic cells through increased DNA damage throughout the body and impaired DNA repair pathways. Acromegaly is a hormone disorder pathological condition
Françoise Nepveu et al.
Journal of medicinal chemistry, 53(2), 699-714 (2009-12-18)
A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), as well as for
Y Shiina et al.
Journal of reproduction and fertility, 97(1), 143-150 (1993-01-01)
Changes in intracellular calcium concentration ([Ca2+]i) in fertilized mouse oocytes were measured using the calcium-sensitive dye, fura-2. After fertilization, an initial long-lasting [Ca2+]i increase was followed by a periodic [Ca2+]i increase. The periodic increase in [Ca2+]i persisted for 1 to
Yvonne E Arnold et al.
Pharmaceutics, 11(3) (2019-03-25)
Drug absorption across viable porcine intestines was investigated using an Ussing chamber system. The apparent permeability coefficients, Papp,pig, were compared to the permeability coefficients determined in humans in vivo, Peff,human. Eleven drugs from the different Biopharmaceutical Classification System (BCS) categories
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