(2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-[(1,1,1,3,3,3-2H6)propan-2-yl]pentanenitrile hydrochloride

• ChemBase ID: 179487
• 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-[(1,1,1,3,3,3-^2H₆)propan-2-yl]pentanenitrile hydrochloride
• IUPAC Traditional name: (2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-[(1,1,1,3,3,3-^2H₆)propan-2-yl]pentanenitrile hydrochloride
• Synonyms: (αS)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl-d6)-benzeneacetonitrile Hydrochloride; (S)-Verapamil-d6 Hydrochloride; (-)-Verapamil-d6 Hydrochloride; (S)-(-)-Verapamil-d6 Hydrochloride; (αR)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)benzeneacetonitrile-d6 Hydrochloride; (R)-Verapamil-d6 Hydrochloride; Dexverapamil-d6 Hydrochloride; LU 33925-d6; NSC 632821-d6; (R)-(+)-Verapamil-d6 Hydrochloride

Database IDs

• PubChem SID: 164235397
• PubChem CID: 71752936

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: 51.541096 Å^3
• Polar Surface Area: 63.95 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V124992

Labelled R-Verapamil (V124990). Both isomers inhibit the p-glycoprotein efflux pump in multidrug resistant tumor cells.

Toronto Research Chemicals - V124993

Labelled S-Verapamil (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)