36622-28-3

Basic information

• Product Name: S(-)-VERAPAMIL
• Synonyms: S(-)-VERAPAMIL;S(-)-VERAPAMIL HYDROCHLORIDE;(-)-[3-cyano-3-(3,4-dimethoxyphenyl)hex-6-yl][2-(3,4-dimethoxyphenyl)ethyl]methylammonium chloride;S(-)-VERAPAMIL HYDROCHLORIDE HYDRATE;Benzeneacetonitrile, a-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-, monohydrochloride, (aS)- (9CI);Benzeneacetonitrile, a-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-, monohydrochloride, (S)-;LU 33926;Benzeneacetonitrile, α-[3-[[2-(3,4-dimethoxyphenyl) ethyl]methylamino]propyl]-3,4-dimethoxy -α-(1-methylethyl)-, monohydrochloride, (αS)-
• CAS NO: 36622-28-3
• Molecular Formula: C₂₇H₃₈N₂O₄*ClH
• Molecular Weight: 454.6
• EINECS: 253-132-8
• Product Categories: Organics;Calcium Channel Modulators;Verapamil;Voltage-gated Ion Channels
• Mol File: 36622-28-3.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/solid
• Density: g/cm³
• Solubility: H2O: >30 mg/mL
• CAS DataBase Reference: S(-)-VERAPAMIL(CAS DataBase Reference)
• NIST Chemistry Reference: S(-)-VERAPAMIL(36622-28-3)
• EPA Substance Registry System: S(-)-VERAPAMIL(36622-28-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 36622-28-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
S(-)-VERAPAMIL is used as an active pharmaceutical ingredient for the treatment of various cardiovascular conditions, such as hypertension, angina, and arrhythmias. Its vasodilatory properties help to relax blood vessels, improving blood flow and reducing blood pressure.
Used in Oncology:
S(-)-VERAPAMIL is used as a chemosensitizer in cancer treatment, particularly for multidrug resistant tumors. By inhibiting the p-glycoprotein efflux pump, it prevents the expulsion of chemotherapeutic drugs from cancer cells, enhancing the effectiveness of these treatments and overcoming drug resistance.
Used in Drug Delivery Systems:
S(-)-VERAPAMIL is also used in the development of novel drug delivery systems, such as nanoparticles and liposomes, to improve the targeted delivery of chemotherapeutic agents to cancer cells. This can help to increase the bioavailability and therapeutic outcomes of these drugs while minimizing side effects on healthy cells.

Biochem/physiol Actions

Active enantiomer of (±)-verapamil. Ca2+ channel (L-type) modulator; adrenoceptor antagonist; cardiac depressant.

InChI:InChI=1/C26H36N2O4.ClH/c1-7-26(19-27,21-10-12-23(30-4)25(18-21)32-6)14-8-15-28(2)16-13-20-9-11-22(29-3)24(17-20)31-5;/h9-12,17-18H,7-8,13-16H2,1-6H3;1H

Upstream product

• 204642-98-8 (S)-verapamilamide 
• 20850-49-1 2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile 
• 36622-23-8 4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid 
• 3490-06-0 N-methylhomoveratrylamine 
• 102201-30-9 4-(3 4-dimethoxyphenyl)-4-cyano-5-methylcapronitrile 

Relevant articles and documents

A scaleable route to the pure enantiomers of verapamil

A versatile route to single enantiomer verapamil from readily available raw materials is described. The key intermediate, 4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid (verapamilic acid), was resolved efficiently with α-methyl benzylamine. Stereochemical integrity at the quaternary carbon centre was preserved through subsequent steps to give either (R)-or (S)-verapamil in good overall yield. This sequence incorporated a selective borane-mediated reduction of a tertiary amide. Process scale-up to the pilot plant has been demonstrated successfully for the resolution step.

Compound and process

A process for the preparation of a compound of formula (VI), optionally in enantiomerically-enriched form (R or S), comprises chemoselective reduction of a novel compound of formula (V), wherein Ar1 and Ar2 are independently selected from optionally-substituted aromatic or heteroaromatic groups having upto 20 C atoms, Ak is C1-20 alkyl, and R is H or C1-20 alkyl. STR1