V4629

(±)-Verapamil hydrochloride

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

• Synonyme(s) : 5-[N-(3,4-Dimethoxyphenylethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride
• Formule linéaire : (CH₃O)₂C₆H₃CH₂CH₂N(CH₃)(CH₂)₃C[C₆H₃(OCH₃)₂][CH(CH₃)₂]CN · HCl
• Numéro CAS: 152-11-4
• Poids moléculaire : 491.06
• NACRES: NA.77
• PubChem Substance ID: 24277881
• UNSPSC Code: 12352200
• EC Number: 205-800-5
• MDL number: MFCD00055208
• Beilstein/REAXYS Number: 3647093
• Assay: ≥99% (titration)
• Form: powder

Propriétés

• Nom du produit: (±)-Verapamil hydrochloride, ≥99% (titration), powder
• Quality Segment: 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
• 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.

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.

Informations sur la sécurité

• pictograms: GHS06,GHS09
• signalword: Danger
• hcodes: H301,H411
• pcodes: P264 - P273 - P301 + P310 - P391 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral - Aquatic Chronic 2
• Classe de stockage: 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
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges