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
• Beilstein: 3647093
• Numéro CE : 205-800-5
• Numéro MDL: MFCD00055208
• Code UNSPSC : 12352200
• ID de substance PubChem : 24277881
• Nomenclature NACRES : NA.77

Propriétés

• Nom du produit: (±)-Verapamil hydrochloride, ≥99% (titration), powder
• Niveau de qualité: 100
• Essai: ≥99% (titration)
• Forme: powder
• Couleur: white
• Pf: 142 °C (dec.) (lit.)
• Solubilité: methanol: 50 mg/mL; ethanol: soluble
• Chaîne SMILES: 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
• Clé InChI: DOQPXTMNIUCOSY-UHFFFAOYSA-N
• Informations sur le gène: 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]

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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

• Pictogrammes: GHS06,GHS09
• Mention d'avertissement: Danger
• Mentions de danger: H301,H411
• Conseils de prudence: P264 - P273 - P301 + P310 - P391 - P405 - P501
• Classification des risques: Acute Tox. 3 Oral - Aquatic Chronic 2
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges