38175-99-4

Basic information

• Product Name: (R)-(+)-Verapamilic Acid
• Synonyms: (R)-(+)-Verapamilic Acid;(R)-4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoic Acid;(R)--Cyano-3,4-dimethoxy--(1-methylethyl)-benzenebutanoic Acid
• CAS NO: 38175-99-4
• Molecular Formula: C16H21NO4
• Molecular Weight: 0
• Product Categories: Aromatics Compounds;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 38175-99-4.mol

Chemical Properties

• Boiling Point: 448.795°C at 760 mmHg
• Flash Point: 225.224°C
• Appearance: /
• Density: 1.127g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform, Dichloromethane (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: (R)-(+)-Verapamilic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-Verapamilic Acid(38175-99-4)
• EPA Substance Registry System: (R)-(+)-Verapamilic Acid(38175-99-4)

Safety Data

• Hazardous Substances Data: 38175-99-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-Verapamilic Acid is used as a precursor for the synthesis of Verapamil, a calcium channel blocker. It plays a crucial role in the development of medications that help regulate heart rate and blood pressure, as well as treat angina and certain heart rhythm disorders.
Used in Cardiovascular Applications:
As a calcium antagonist, (R)-(+)-Verapamilic Acid is used in the development of drugs that target the cardiovascular system. These medications are effective in managing conditions such as hypertension, coronary artery disease, and arrhythmias by blocking the movement of calcium ions into heart and blood vessel cells, thus relaxing the blood vessels and reducing the workload on the heart.
Chemical Properties:
(R)-(+)-Verapamilic Acid is a white solid with unique chemical properties that contribute to its effectiveness as a precursor in the pharmaceutical industry. Its chiral nature allows for the development of targeted therapies with fewer side effects, making it a valuable compound in the synthesis of calcium channel blockers and other related medications.

InChI:InChI=1/C16H21NO4/c1-11(2)16(10-17,8-7-15(18)19)12-5-6-13(20-3)14(9-12)21-4/h5-6,9,11H,7-8H2,1-4H3,(H,18,19)/t16-/m1/s1

Upstream product

• 36770-70-4 2-(3,4-dimethoxyphenyl)-5-hydroxy-2-(methylethyl)pentanenitrile 
• 102201-30-9 4-(3 4-dimethoxyphenyl)-4-cyano-5-methylcapronitrile 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 36622-23-8 4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 20850-49-1 2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile 

Downstream Products

• 204642-98-8 (S)-verapamilamide 
• 204642-98-8 (R)-verapamilamide 
• 36622-28-3 (-)-Verapamil hydrochloride 
• 152-11-4 (+)-Verapamil hydrochloride 
• 36622-24-9 (S)-verapamilic acid 
• 36622-24-9 (R)-verapamilic acid 
• 204642-98-8 verapamilamide 

Relevant articles and documents

Design, synthesis, and preliminary pharmacological evaluation of 4-aminopiperidine derivatives as N-type calcium channel blockers active on pain and neuropathic pain

Several compounds with a 4-aminopiperidine scaffold decorated on both nitrogen atoms by alkyl or acyl moieties containing the structural motifs of verapamil and of flunarizine, as well as those that are more frequent in known N-type calcium channel antago

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.