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

• ChemBase ID: 179486
• Molecular Formular: C27H39ClN2O4
• Molecular Mass: 491.06256
• Monoisotopic Mass: 490.25983542
• SMILES: c1(c(ccc(c1)CCN(CCC[C@](c1ccc(c(c1)OC)OC)(C(C)C)C#N)C)OC)OC.Cl
• Canonical SMILES: COc1ccc(cc1OC)CCN(CCC[C@](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/t27-;/m1./s1
• InChIKey: DOQPXTMNIUCOSY-HZPIKELBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile hydrochloride
• IUPAC Traditional name: verapamil hcl hydrochloride
• Synonyms: (αR)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-benzeneacetonitrile Hydrochloride; (R)-Verapamil Hydrochloride; Dexverapamil Hydrochloride; LU 33925; NSC 632821; (R)-(+)-Verapamil Hydrochloride; (αS)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-benzeneacetonitrile Hydrochloride; (S)-Verapamil Hydrochloride; (-)-Verapamil Hydrochloride; (S)-(-)-Verapamil Hydrochloride

Database IDs

• CAS Number: 38176-02-2; 36622-29-4
• PubChem SID: 164235396
• PubChem CID: 170014

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: Methanol; Water
• Apperance: Off-White Solid; White Solid
• Melting Point: 126-129°C; 129-131°C

Safety Information

• Storage Condition: -20°C Freezer; Refrigerator

DETAILS

Toronto Research Chemicals - V124990

Both isomers inhibit the p-glycoprotein efflux pump in multidrug resistant tumor cells.

Toronto Research Chemicals - V124991

Both isomers inhibit the p-glycoprotein efflux pump in multidrug resistant tumor cells.

REFERENCES

• Peroutka, S., et al.: J. Ann. Neurol, 23, 500 (1988)
• Eliason, J.F., et al.: Int. J. Cancer, 46, 113 (1988)
• Peroutka, S., et al.: J. Ann. Neurol, 23, 500 (1988)
• Eliason, J.F., et al.: Int. J. Cancer, 46, 113 (1988)