2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile hydrochloride

• ChemBase ID: 53601
• Molecular Formular: C27H39ClN2O4
• Molecular Mass: 491.06256
• Monoisotopic Mass: 490.25983542
• SMILES: C(c1cc(c(cc1)OC)OC)(C#N)(C(C)C)CCCN(CCc1cc(c(cc1)OC)OC)C.Cl
• Canonical SMILES: COc1ccc(cc1OC)CCN(CCCC(c1ccc(c(c1)OC)OC)(C(C)C)C#N)C.Cl
• InChI: 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
• InChIKey: DOQPXTMNIUCOSY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile hydrochloride
• IUPAC Traditional name: verapamil hydrochloride; veraβ hydrochloride
• Synonyms: 2-(3,4-Dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)-ethyl](methyl)amino]-2-isopropylpentanenitrile hydrochloride; 5-[N-(3,4-Dimethoxyphenylethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride; (±)-Verapamil hydrochloride; (±)-Verapamil hydrochloride; Verapamil hydrochloride; α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-benzeneacetonitrile Hydrochloride; Berkatens; Calan; Cardibeltin; Dignover; Isoptin; Veracim; Veramex; Zolvera; Verapamil Hydrochloride; R(+)-VERAPAMIL; Verapamil HCl; 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile hydrochloride

Database IDs

• CAS Number: 38176-10-2; 23313-68-0; 152-11-4
• EC Number: 205-800-5
• MDL Number: MFCD00055208
• Beilstein Number: 3647093
• PubChem SID: 162058364; 24277881; 24890064; 24863792
• PubChem CID: 62969

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.6246759
• LogD (pH = 7.4): 2.7877045
• Log P: 5.0431857
• Molar Refractivity: 132.6479 cm^3
• Polarizability: 51.54108 Å^3
• Polar Surface Area: 63.95 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 7g/100g water (pH=4.24); Acetone; Ethanol; ethanol: soluble; Ethyl Acetate; H2O: soluble50 mg/mL; Isopropanol; methanol: soluble50 mg/mL, clear, colorless
• Apperance: white powder; White Solid
• Melting Point: 138-140°C; 142 - 144°C; 142 °C (dec.)(lit.)
• Hydrophobicity(logP): 4.466

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C), Protect from light
• Storage Warning: IRRITANT
• RTECS: YV8320000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 23/24/25; R:25
• Safety Statements: 36/37-45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Pharmacology Properties

• Target: Others
• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146)

Product Information

• Purity: ≥99.0% (titration); ≥99.0% (TLC); 95%; 98%
• Grade: certified reference material
• Salt Data: HCl
• Packaging: pkg of 1 g
• Pharmacopeia Traceability: traceable to PhEur V0100000; traceable to USP 1711202
• Linear Formula: (CH3O)2C6H3CH2CH2N(CH3)(CH2)3C[C6H3(OCH3)2][CH(CH3)2]CN · HCl

DETAILS

MP Biomedicals - 02153586

Hydrochloride

Sigma Aldrich - V4629

包装
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.

Sigma Aldrich - 381195

Packaging
1 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.

Sigma Aldrich - PHR1131

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
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.

Sigma Aldrich - 94837

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.

Toronto Research Chemicals - V125000

A calcium channel blocker. Antihypertensive; antianginal; antiarrhythmic (class IV).

REFERENCES

• Atlas, D, and Adler, M.: Proc. Natl. Acad. Sci. USA, 78, 1237 (1981)
• Janis, R., et al.: Adv. Drug. Res., 16, 309 (1987)