123931-31-7

Basic information

• Product Name: (S)-(-)-Norverapamil Hydrochloride
• Synonyms: (aS)-a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]amino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-benzeneacetonitrile Hydrochloride;(S)-(-)-Norverapamil Hydrochloride;(S)-Norverapamil Hydrochlorid;Benzeneacetonitrile, a-[3-[[2-(3,4-dimethoxyphenyl)-ethyl]amino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-, (aS)-;S-Norverapamil;(aS)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]amino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-benzeneacetonitrile Hydrochloride;(αS)-α-[3-[[2-(3,4-DiMethoxyphenyl)ethyl]aMino]propyl]-3,4-diMethoxy-α-(1-Methylethyl)-benzeneacetonitrile Hydrochloride
• CAS NO: 123931-31-7
• Molecular Formula: C₂₆H₃₆N₂O₄
• Molecular Weight: 440.58
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 123931-31-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 131-133°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: (S)-(-)-Norverapamil Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-Norverapamil Hydrochloride(123931-31-7)
• EPA Substance Registry System: (S)-(-)-Norverapamil Hydrochloride(123931-31-7)

Safety Data

• Hazardous Substances Data: 123931-31-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish to brownish oil

Uses

The metabolite of (S)-Verapamil

InChI:InChI=1/C26H36N2O4.ClH/c1-19(2)26(18-27,21-9-11-23(30-4)25(17-21)32-6)13-7-14-28-15-12-20-8-10-22(29-3)24(16-20)31-5;/h8-11,16-17,19,28H,7,12-15H2,1-6H3;1H/t26-;/m0./s1

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 52-53-9 Verapamil 
• 27487-83-8 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 20850-49-1 2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile 
• 67018-85-3 norverapamil 

Downstream Products

• 67018-85-3 (+)-Norverapamil 
• 36622-29-4 (S)-verapamil 
• 1228254-18-9 2-(3,4-dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl]-(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-ylmethyl)-amino]-2-isopropyl-pentanenitrile radical 
• 1228254-19-0 2-(3,4-dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl]-(1-oxyl-2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-ylmethyl)amino]-2-isopropyl-pentanenitrile radical 
• 1616284-78-6 5-{cyclopropyl-[2-(3,4-dimethoxy-phenyl)-ethyl]-amino}-2-(3,4-dimethoxy-phenyl)-2-isopropyl-pentanenitrile 
• 1616074-40-8 nor-verapamil 
• 1616074-56-6 5-((3,4-dimethoxyphenethyl)(2-fluoroethyl)amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile 

Relevant articles and documents

Synthesis of new verapamil analogues and their evaluation in combination with rifampicin against Mycobacterium tuberculosis and molecular docking studies in the binding site of efflux protein Rv1258c

New verapamil analogues were synthesized and their inhibitory activities against Mycobacterium tuberculosis H37Rv determined in vitro alone and in combination with rifampicin (RIF). Some analogues showed comparable activity to verapamil and exhibited better synergies with RIF. Molecular docking studies of the binding sites of Rv1258c, a M. tuberculosis efflux protein previously implicated in intrinsic resistance to RIF, suggested a potential rationale for the superior synergistic interactions observed with some analogues.

A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds

Herein we demonstrate that a small panel of variants of cytochrome P450 BM3 from Bacillus megaterium covers the breadth of reactivity of human P450s by producing 12 of 13 mammalian metabolites for two marketed drugs, verapamil and astemizole, and one research compound. The most active enzymes support preparation of individual metabolites for preclinical bioactivity and toxicology evaluations. Underscoring their potential utility in drug lead diversification, engineered P450 BM3 variants also produce novel metabolites by catalyzing reactions at carbon centers beyond those targeted by animal and human P450s. Production of a specific metabolite can be improved by directed evolution of the enzyme catalyst. Some variants are more active on the more hydrophobic parent drug than on its metabolites, which limits production of multiply-hydroxylated species, a preference that appears to depend on the evolutionary history of the P450 variant.

Process for the preparation of basically substituted phenylacetonitriles

A simplified process for the preparation of basically substituted phenylacetonitriles, in particular of verapamil, is described. This process is carried out with fewer stages and higher yields than the known processes according to the state of the art.