(S)-Verapamil
Basic information
- CAS
36622-29-4- Standard SMILES
COc1ccc(CCN(C)CCC[C@@](C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC- InChIKey
SGTNSNPWRIOYBX-MHZLTWQESA-N- Molecular formula
- C27H38N2O4
- Average molar mass
- 454.6 g/mol
- Monoisotopic mass
- 454.2831577
Overview
(S)-verapamil is a 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile that has S configuration. It is a conjugate base of a (S)-verapamil(1+). It is an enantiomer of a dexverapamil.
Names & identifiers
- Preferred name
- (S)-Verapamil
- IUPAC
- (2S)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
- English name
- (-)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile
- Molecular formula
- C27H38N2O4
- Molecular weight
- 454.6
Names & synonyms
(S)-VERAPAMIL(S) Verapamil(2S)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrileCHEBI:77736(2S)-2-(3,4-dimethoxyphenyl)-5-(2-(3,4-dimethoxyphenyl)ethyl-methylamino)-2-propan-2-ylpentanenitrileRefChem:1051214(-)-verapamil36622-29-4(S)-(-)-verapamil(-)-(S)-verapamil(S)-5-((3,4-dimethoxyphenethyl)(methyl)amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrileCHEMBL36148
Show more names
l-VerapamilS-Verapamil HCIEinecs 253-133-3l-a-Isopropyl-a-[(N-methyl-N-homoveratryl)-g-aminopropyl]-3,4-dimethoxyphenylacetonitrile(S)-5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile[S,(-)]-2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-(N-methyl-3,4-dimethoxyphenethylamino)valeronitrile(-)-(S)-5-[N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile(S)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)benzeneacetonitrile
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 64 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 13
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 606
Physicochemical properties
- Melting point
- 126 · 126-129°C
- Boiling point
- 586.1 · 586.1±50.0 °C(Predicted)
- Density
- 1.058 · 1.058±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- pka
- 8.97 · 8.97±0.50(Predicted)
- FDA UNII
- 9 P7619E627 · 9P7619E627
Chemistry & industry
Applications
UsesBoth isomers inhibit the p-glycoprotein efflux pump in multidrug resistant tumor cells
Additional notes
DefinitionChEBI: (S)-verapamil is a 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile that has S configuration. It is a conjugate base of a (S)-verapamil(1+). It is an enantiomer of a dexverapamil.
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