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CAS 36622-29-4

:

(-)-Verapamil

Description:
(-)-Verapamil is a calcium channel blocker primarily used in the treatment of hypertension, angina, and certain heart rhythm disorders. It is a chiral compound, with the "(-)" designation indicating its specific enantiomer, which exhibits distinct pharmacological properties compared to its counterpart. The molecular formula of (-)-Verapamil is C27H38N2O5, and it features a complex structure that includes a phenylalkylamine moiety. This compound works by inhibiting the influx of calcium ions through L-type calcium channels in cardiac and smooth muscle cells, leading to vasodilation and reduced heart contractility. (-)-Verapamil is also known for its ability to affect the metabolism of other drugs by inhibiting cytochrome P450 enzymes, particularly CYP3A4. Its pharmacokinetics include extensive hepatic metabolism and a relatively long half-life, allowing for once or twice daily dosing. Common side effects may include hypotension, bradycardia, and gastrointestinal disturbances. Overall, (-)-Verapamil is a vital therapeutic agent in cardiovascular medicine, with a well-established profile in clinical use.
Formula:C27H38N2O4
InChI:InChI=1S/C27H38N2O4/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/t27-/m0/s1
InChI key:InChIKey=SGTNSNPWRIOYBX-MHZLTWQESA-N
SMILES:[C@@](CCCN(CCC1=CC(OC)=C(OC)C=C1)C)(C(C)C)(C#N)C2=CC(OC)=C(OC)C=C2
Synonyms:
  • (-)-(S)-Verapamil
  • (-)-Verapamil
  • (2S)-2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentanenitrile
  • (2S)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
  • (αS)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)benzeneacetonitrile
  • 2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-Dimethoxyphenyl)Ethyl](Methyl)Amino}-2-(Propan-2-Yl)Pentanenitrile
  • Benzeneacetonitrile, Alpha-[3-[[2-(3,4-Dimethoxyphenyl)Ethyl]Methylamino]Propyl]-3,4-Dimethoxy-Alpha-(1-Methylethyl)-
  • Benzeneacetonitrile, α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-, (S)-
  • Benzeneacetonitrile, α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-, (αS)-
  • benzeneacetonitrile, alpha-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-alpha-(1-methylethyl)-, (alphaS)-
  • See more synonyms
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