(S)-Norverapamil

Base Information

• Chemical Name: (S)-Norverapamil
• CAS No.: 123931-31-7
• Molecular Formula: C26H36 N2 O4
• Molecular Weight: 440.583
• UNII: 20YAJ9077G
• DSSTox Substance ID: DTXSID401316755
• Nikkaji Number: J628.624K
• Wikidata: Q27253491
• Mol file: 123931-31-7.mol

Synonyms:(S)-Norverapamil;123931-31-7;Norverapamil, (S)-;UNII-20YAJ9077G;20YAJ9077G;(2RS)-2-(3,4-Dimethoxyphenyl)-5-((2-(3,4-dimethoxy-phenyl)ethyl)amino)-2-(1-methylethyl)pentanenitrile;(2S)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethylamino]-2-propan-2-ylpentanenitrile;Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)amino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-, (alphaS)-;Benzeneacetonitrile, alpha-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-3,4-dimethoxy-alpha-(1-methylethyl)-, (alphaS)-;(-)-norverapamil;(S)-desmethylverapamil;(-)-desmethylverapamil;CHEBI:134081;DTXSID401316755;Q27253491;(2S)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile;BENZENEACETONITRILE, .ALPHA.-(3-((2-(3,4-DIMETHOXYPHENYL)ETHYL)AMINO)PROPYL)-3,4-DIMETHOXY-.ALPHA.-(1-METHYLETHYL)-, (.ALPHA.S)-

Chemical Property of (S)-Norverapamil

Chemical Property:

• Melting Point: 131-133°C
• PSA: 72.74000
• LogP: 5.14178
• Storage Temp.: -20°C Freezer
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 440.26750763
• Heavy Atom Count: 32
• Complexity: 577

Purity/Quality:

99% ^*data from raw suppliers

(S)-(-)-NorverapamilHCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CCCNCCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
• Isomeric SMILES: CC(C)[C@](CCCNCCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
• Uses: The metabolite of (S)-Verapamil

Technology Process of (S)-Norverapamil

There total 17 articles about (S)-Norverapamil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 37.0%

2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile (27487-83-8) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → norverapamil (67018-85-3,73980-36-6,123931-31-7,123932-43-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 12h;

DOI:10.1016/j.bmcl.2014.05.022

Reference yield:

Verapamil (52-53-9,56949-77-0) → D 620 (27487-66-7) + 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-methylamino-pentanenitrile (34245-14-2) + norverapamil (67018-85-3,73980-36-6,123931-31-7,123932-43-4)

Guidance literature:

With NADPH; In water; dimethyl sulfoxide; at 37 ℃; for 1h; Microbiological reaction;

DOI:10.1002/rcm.4465

Reference yield:

Verapamil (52-53-9,56949-77-0) → 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-methylamino-pentanenitrile (34245-14-2) + norverapamil (67018-85-3,73980-36-6,123931-31-7,123932-43-4) + D 702

Guidance literature:

With cytochrome P₄₅₀ BM₃ chimera variant 11113311; at 37 ℃; for 1h; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/chem.200900643

upstream raw materials:

2-(3,4-dimethoxyphenyl)-ethylamine

Verapamil

2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile

3,4-dimethoxyphenylacetonitrile

Downstream raw materials:

(+)-Norverapamil

5-{cyclopropyl-[2-(3,4-dimethoxy-phenyl)-ethyl]-amino}-2-(3,4-dimethoxy-phenyl)-2-isopropyl-pentanenitrile

nor-verapamil

(S)-verapamil