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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

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Properties

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
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
• 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)

Packaging

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

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all
WGK Germany 
WGK 3
RTECS 
YV8320000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Antihypertensive Agents

Agents that inhibit angiontensin-converting enzymes (ACE) and angiotensin II formation are essential to cardiovascular medicine.1 These inhibitors are used not only to treat essential hypertension an...
Sami Barghshoon
BioFiles v7 n5, 2012, 5–20
Keywords: AGE, Antihypertensives, Cardiovascular, Clinical, Diuretics, PAGE, Reductions

Cancer Stem Cell Detection Utilizing a Red-shifted Fluorescent Live Cell Probe for Aldehyde Dehydrogenase (ALDH), AldeRed™ 588-A.

Introduction Methods    Reagent Preparation    Stem Cell Sample Preparation    AldeRed ALDH Assay    Flow Cytometry Analysis Results Materials
Nick Asbrock1, Konstantin Taganov1, Vi Chu1, Martin G. Pomper2, Il Minn2, Haofan Wang2, Steven D. Leach2

1Assay & Platform Development, Bioscience BU, MilliporeSigma, 28820 Single Oak Drive, Temecula, CA, USA 9259
2Johns Hopkins Russel H. Morgan Department of Radiology and Radiological Science, Baltimore, Maryland 21287, USA.
Keywords: Cancer, Enzyme activity, Evaporation, Flow cytometry, Oxidations, Sample preparations

Discover Bioactive Small Molecules for ADME/Tox

A significant number of drugs that fail in clinical trials have been associated with safety issues, including unexpected drug-drug interactions (DDI) or lack of efficacy due to poor pharmacokinetics....
Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

Discover Bioactive Small Molecules for Ion Channels Research

Ion transport across the relatively impermeable lipid bilayer of the cell membrane is accomplished via membrane proteins known as ion channels, pumps and transporters. Ion channels are gated pores an...
Keywords: Biological processes, Cell signaling, Diseases, Hormones, Ligands, Neurotransmitters

Peer-Reviewed Papers
15

References

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