V4629

(±)-Verapamil hydrochloride

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

• 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
• UNSPSC Code: 12352200
• PubChem Substance ID: 24277881
• NACRES: NA.77

Properties

• Product Name: (±)-Verapamil hydrochloride, ≥99% (titration), powder
• 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)

Description

Application

Verapamil hydrochloride has been used:

• to inhibit calcium oscillation in fertilized oocyte[1]
• to block calcium channel, thereby blocking the action of IL-1β (interleukin-1β), resulting in membrane depolarization[2]
• to investigate the effect of verapamil on cytotoxicity of 1,3-dilinoleoylglycerol (DLG)[3]

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.

Safety Information

• 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