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V4629

(±)-Verapamil hydrochloride

Name: (±)-Verapamil hydrochloride
Brand: SIGMA

≥99% (titration), powder

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Synonym(s):

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

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:

3647093

EC Number:

205-800-5

MDL number:

MFCD00055208

PubChem Substance ID:

24277881

NACRES:

NA.77

Quality Level

100

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

GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301 - H411

Precautionary Statements

P264 - P273 - P301 + P310 - P391 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Intracellular signaling mechanisms of interleukin-1beta in synovial fibroblasts.

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

An Acromegaly Disease Zebrafish Model Reveals Decline in Body Stem Cell Number along with Signs of Premature Aging.

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

Role of the extracellular Ca2+ on the intracellular Ca2+ changes in fertilized and activated mouse oocytes.

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

Drug Transport across Porcine Intestine Using an Ussing Chamber System: Regional Differences and the Effect of P-Glycoprotein and CYP3A4 Activity on Drug Absorption.

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

Synthesis and antiplasmodial activity of new indolone N-oxide derivatives.

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

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