(-)-Verapamil Hydrochloride

Base Information

• Chemical Name: (-)-Verapamil Hydrochloride
• CAS No.: 36622-28-3
• Molecular Formula: C26H37ClN2O4
• Molecular Weight: 491.071
• European Community (EC) Number: 253-132-8
• UNII: 5002H7B3FO
• Wikidata: Q27147338
• Mol file: 36622-28-3.mol

Synonyms:36622-28-3;(-)-Verapamil Hydrochloride;(S)-(-)-Verapamil Hydrochloride;(S)-Verapamil (hydrochloride);S(-)-VERAPAMIL;(S)-Verapamil Hydrochloride;Verapamil hydrochloride, (-)-;5002H7B3FO;(S)-(-)-Verapamil (hydrochloride);(2S)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile;hydrochloride;(S)-5-((3,4-Dimethoxyphenethyl)(methyl)amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile hydrochloride;S(-)-Verapamil hydrochloride hydrate;(S)-verapamil HCl;(S)-verapamil.HCl;starbld0016677;?S(-)-VERAPAMIL;UNII-5002H7B3FO;SCHEMBL8759334;CHEBI:77741;EINECS 253-132-8;CCG-35758;CCG-36091;AKOS030530539;HY-135336A;LU 33926;LU-33926;MS-29128;CS-0111669;VERAPAMIL (S)-FORM HYDROCHLORIDE [MI];Q27147338;(-)-(3-Cyano-3-(3,4-dimethoxyphenyl)hex-6-yl)(2-(3,4-dimethoxyphenyl)ethyl)methylammonium chloride;(2S)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentanenitrile hydrochloride;(4S)-4-cyano-4-(3,4-dimethoxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N,5-dimethylhexan-1-aminium chloride;BENZENEACETONITRILE, .ALPHA.-(3-((2-(3,4-DIMETHOXYPHENYL)ETHYL)METHYLAMINO)PROPYL)-3,4-DIMETHOXY-.ALPHA.-(1-METHYLETHYL)-, MONOHYDROCHLORIDE, (.ALPHA.S)-;BENZENEACETONITRILE, .ALPHA.-(3-((2-(3,4-DIMETHOXYPHENYL)ETHYL)METHYLAMINO)PROPYL)-3,4-DIMETHOXY-.ALPHA.-(1-METHYLETHYL)-, MONOHYDROCHLORIDE, (S)-;Benzeneacetonitrile, .alpha.-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-.alpha.-(1-methylethyl)-, (.alpha.S)-, hydrochloride (1:1)

Chemical Property of (-)-Verapamil Hydrochloride

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 63.95000
• Density: g/cm³
• LogP: 5.89508
• Solubility.: H2O: >30 mg/mL
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 490.2598354
• Heavy Atom Count: 34
• Complexity: 606

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC.Cl
• Isomeric SMILES: CC(C)[C@](CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC.Cl
• Uses: Both isomers inhibit the p-glycoprotein efflux pump in multidrug resistant tumor cells.

Technology Process of (-)-Verapamil Hydrochloride

There total 6 articles about (-)-Verapamil Hydrochloride 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: 85.0%

(S)-verapamilamide (204642-98-8) → (-)-Verapamil hydrochloride (36622-28-3,152-11-4)

Guidance literature:

(S)-verapamilamide; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 25 ℃; for 16h;

With hydrogenchloride; In tetrahydrofuran; water;

DOI:10.1021/op000059q

Reference yield:

4-(3 4-dimethoxyphenyl)-4-cyano-5-methylcapronitrile (102201-30-9) → (-)-Verapamil hydrochloride (36622-28-3,152-11-4)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydroxide / ethanol; water / Large scale

2: ethyl acetate / 2 h / 60 - 65 °C / Large scale

3: m-nitrobenzene boronic acid / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 40 °C / Reflux

4: dimethylsulfide borane complex / tetrahydrofuran / 16 h / 0 - 25 °C

With dimethylsulfide borane complex; m-nitrobenzene boronic acid; potassium hydroxide; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; ethanol; water; ethyl acetate;

DOI:10.1021/op000059q

Reference yield:

4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid (36622-23-8,36622-24-9,38175-99-4) → (-)-Verapamil hydrochloride (36622-28-3,152-11-4)

Guidance literature:

Multi-step reaction with 3 steps

1: ethyl acetate / 2 h / 60 - 65 °C / Large scale

2: m-nitrobenzene boronic acid / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 40 °C / Reflux

3: dimethylsulfide borane complex / tetrahydrofuran / 16 h / 0 - 25 °C

With dimethylsulfide borane complex; m-nitrobenzene boronic acid; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetate;

DOI:10.1021/op000059q

upstream raw materials:

4-(3 4-dimethoxyphenyl)-4-cyano-5-methylcapronitrile

N-methylhomoveratrylamine

4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid

2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile