34245-14-2

Basic information

• Product Name: RAC D 617 (N-METHYL-4-(3,4-DIMETHOXYPHENYL)-4-CYANO-5-METHYLHEXYLAMINE)
• Synonyms: RAC D 617 (N-METHYL-4-(3,4-DIMETHOXYPHENYL)-4-CYANO-5-METHYLHEXYLAMINE);3-(3,4-dimethoxyphenyl)-2-methyl-6-methylaminohexane-3-carbonitrile; 2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-(methylamino)-valeronitrile;3,4-Dimethoxy-a-[3-(methylamino)propyl]-a-(1-methylethyl)-benzeneacetonitrile;D 617;3,4-Dimethoxy-α-[3-(methylamino)propyl]-α-(1-methylethyl)-benzeneacetonitrile;2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-(methylamino)pentanenitrile;2-Isopropyl-2-(3,4-dimethoxyphenyl)-5-(methylamino)pentanenitrile
• CAS NO: 34245-14-2
• Molecular Formula: C₁₇H₂₆N₂O₂
• Molecular Weight: 290.40054
• EINECS: 251-895-1
• Product Categories: Chemical Amines;Amines;Aromatics;Metabolites & Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 34245-14-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 429.1°Cat760mmHg
• Flash Point: 213.3°C
• Appearance: /
• Density: 1.004g/cm³
• Vapor Pressure: 1.43E-07mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: RAC D 617 (N-METHYL-4-(3,4-DIMETHOXYPHENYL)-4-CYANO-5-METHYLHEXYLAMINE)(CAS DataBase Reference)
• NIST Chemistry Reference: RAC D 617 (N-METHYL-4-(3,4-DIMETHOXYPHENYL)-4-CYANO-5-METHYLHEXYLAMINE)(34245-14-2)
• EPA Substance Registry System: RAC D 617 (N-METHYL-4-(3,4-DIMETHOXYPHENYL)-4-CYANO-5-METHYLHEXYLAMINE)(34245-14-2)

Safety Data

• Hazardous Substances Data: 34245-14-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

A metabolite of Verapamil (V125000).

Definition

ChEBI: A nitrile that is pentanenitrile substituted by a 3,4-dimethoxyphenyl group at position 2, a methylamino group at position 4 and an isopropyl group at position 2. It is a metabolite of the drug verapamil.

InChI:InChI=1/C17H26N2O2/c1-13(2)17(12-18,9-6-10-19-3)14-7-8-15(20-4)16(11-14)21-5/h7-8,11,13,19H,6,9-10H2,1-5H3

Upstream product

• 27487-83-8 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile 
• 74-89-5 methylamine 
• 52-53-9 Verapamil 
• 20850-49-1 2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 42601-11-6 (dimethoxy-3,4 phenyl)-2 (N-methyl N-formyl amino-3 propyl)-2 isovaleronitrile 

Downstream Products

• 101532-49-4 2-(3,4-Dimethoxy-phenyl)-5-{[2-hydroxy-3-(2-methoxy-phenoxy)-propyl]-methyl-amino}-2-isopropyl-pentanenitrile 
• 1246457-25-9 2-(3,4-dimethoxy-phenyl)-2-isopropyl-5-{[2-(4-methoxy-phenyl)-ethyl]-methyl-amino}-pentanenitrile 
• 1246457-17-9 2-(3,4-dimethoxy-phenyl)-5-{[2-(4-hydroxy-phenyl)-ethyl]-methyl-amino}-2-isopropyl-pentanenitrile 
• 1246457-14-6 2-(3,4-dimethoxy-phenyl)-5-[(4-hydroxy-benzyl)-methyl-amino]-2-isopropyl-pentanenitrile 
• 1246457-27-1 5-{[2-(3,5-diiodo-4-methoxy-phenyl)-ethyl]-methylamino}-2-(3,4-dimethoxy-phenyl)-2-isopropyl-pentanenitrile 
• 1246457-26-0 2-(3,4-dimethoxy-phenyl)-5-{[2-(3-iodo-4-methoxyphenyl)-ethyl]-methyl-amino}-2-isopropyl-pentanenitrile 
• 1246457-19-1 2-(3,4-dimethoxy-phenyl)-5-{[3-(4-hydroxy-phenyl)-propyl]-methyl-amino}-2-isopropyl-pentanenitrile 
• 102336-10-7 2-[4-cyano-4-(3,4-dimethoxyphenyl)-5,N-dimethyl-hexylamino]-1-methylethanol 
• 102336-09-4 Methyl 2-[4-cyano-4-(3,4-dimethoxyphenyl)-5,N-dimethyl-hexylamino]-ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate 
• 101532-61-0 5-{[3-(2-Allyloxy-phenoxy)-2-hydroxy-propyl]-methyl-amino}-2-(3,4-dimethoxy-phenyl)-2-isopropyl-pentanenitrile 
• 129975-57-1 2-(3-{[4-Cyano-4-(3,4-dimethoxy-phenyl)-5-methyl-hexyl]-methyl-amino}-2-hydroxy-propoxy)-benzonitrile 
• 129975-56-0 2-(3,4-Dimethoxy-phenyl)-5-[(2-hydroxy-3-o-tolyloxy-propyl)-methyl-amino]-2-isopropyl-pentanenitrile 
• 128564-69-2 2-(3,4-Dimethoxy-phenyl)-2-isopropyl-5-{methyl-[2-(1-triisopropylsilanyl-1H-indol-5-yl)-ethyl]-amino}-pentanenitrile 
• 129975-52-6 2-(3,4-Dimethoxy-phenyl)-5-{[2-hydroxy-3-(naphthalen-1-yloxy)-propyl]-methyl-amino}-2-isopropyl-pentanenitrile 

Relevant articles and documents

Design, synthesis and evaluation of 9-hydroxy-7H-furo [3,2-g]chromen-7-one derivatives as new potential vasodilatory agents

Two new 9-hydroxy-7H-furo[3,2-g]chromen-7-one derivatives were designed, synthesized and evaluated for their in vitro vasodilatory activity. The structures of two compounds were elucidated by infrared, 1H NMR, and mass spectral data. The invitro pharmacological evaluation indicated that both of them possessed well vasodilatory activity compared with imperatorin. The molecule docking also showed two target compounds docked well with L-calcium channel (PDB code: 3G43). The result suggested that they would be potential vasodilatory agents for hypertension.

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.

Antagonistes calciques. I. Remplacement du groupe dimethoxy-3,4- phenylethyle du verapamil

In the verapamil structure, the 3,4-dimethoxy phenylethyl group has been replaced by several moieties belonging to α- and β-blockers or other classes of calcium channel blockers.The best derivatives, as calcium blockers, were prepared with β-blocker fragments like aryloxypropanolamines (AOPA) with an ortho substituent on the aromatic ring.