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V4629 Sigma-Aldrich

(±)-Verapamil hydrochloride

≥99% (titration), powder

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

  • CAS Number 152-11-4

  • Linear Formula (CH3O)2C6H3CH2CH2N(CH3)(CH2)3C[C6H3(OCH3)2][CH(CH3)2]CN · HCl

  • Molecular Weight 491.06

  •  Beilstein/REAXYS Number 3647093

  •  EC Number 205-800-5

  •  MDL number MFCD00055208

  •  PubChem Substance ID 24277881

  •  NACRES NA.77



Related Categories Application Index, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
Quality Level   100
assay   ≥99% (titration)
form   powder
color   white
mp   142 °C (dec.) (lit.)
solubility   methanol: 50 mg/mL
  ethanol: soluble
originator   Pfizer
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
Gene Information   human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), CACNA1C(775), CACNA1D(776), CACNA1F(778), CACNA1S(779)



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)


1, 5, 10 g in glass bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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.

This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Signal word 
Hazard statements 
Precautionary statements 
UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles


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