91599-74-5

Basic information

• Product Name: Benidipine hydrochloride
• Synonyms: (R,R)-(+/-)-2,6-DIMETHYL-4-(3-NITROPHENYL)-1,4-DIHYDRO-3,5-PYRIDINE,DICARBOXYLIC ACID METHYL-1-BENZYL-3-PIPERIDYL-ESTER,MONOHYDROCHLORIDE SALT;monohydrochloride,(r*,r*)-(+-)-hyl1-(phenylmethyl)-3-piperidinyleste;1-(BENZYLMETHYL)-3-PIPERIDINYL 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-3,5-PYRIDINEDICARBOLATE;2,6-Dimethyl-4-(3-Nitrophenyl)-1,4-Dihydropyridine-3,5-DimethoxyCarboxylate;(R,R)-(+/)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylicacidmethyl-1-(phenylmethyl)-3-piperidiny;Coniel, Capadipine, KW-3049, Nacadipine;3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl (3R)-1-(phenylmethyl)-3-piperidinyl ester, monohydrochloride, (4R)-rel-;3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 1-(phenylmethyl)-3-piperidinyl ester, monohydrochloride, (R*,R*)-(+-)-
• CAS NO: 91599-74-5
• Molecular Formula: C₂₈H₃₁N₃O₆*ClH
• Molecular Weight: 505.56
• EINECS: 1592732-453-0
• Product Categories: Antihypertensive;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Chiral Reagents;Heterocycles;Inhibitors
• Mol File: 91599-74-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 199-201°C
• Boiling Point: 625.2 °C at 760 mmHg
• Flash Point: 331.9 °C
• Appearance: yellow/
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: ≥20mg/mL
• PKA: 7.34(at 25℃)
• CAS DataBase Reference: Benidipine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Benidipine hydrochloride(91599-74-5)
• EPA Substance Registry System: Benidipine hydrochloride(91599-74-5)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• RTECS: US7975657
• Hazardous Substances Data: 91599-74-5(Hazardous Substances Data)

Usage

Description

Benidipine hydrochloride, also known as Coniel, is a long-acting dihydropyridine calcium antagonist that serves as an orally bioavailable blocker of L-, T-, and N-type calcium channels. It is a yellow crystalline powder with potent hypotensive effects and neuroprotective properties, making it useful in the treatment of hypertension and angina pectoris.
Used in Pharmaceutical Industry:
Benidipine hydrochloride is used as an antihypertensive agent for its ability to induce hypotension with a potency 6 and 12 times more than nifedipine and nicardipine, respectively. Its slow onset of action and neuroprotective properties for neural stem cells after oxidative stress-induced injury make it a valuable treatment option for hypertension and angina pectoris.
Additionally, Benidipine hydrochloride is used as a calcium channel blocker for its IC50 of 2.7 nM for calcium currents in guinea pig ventricular cells, as determined using whole cell voltage clamp electrophysiology. This property allows it to prevent oxidative stress dose-dependently in vitro and decrease blood pressure in spontaneously hypertensive rats.
Furthermore, Benidipine hydrochloride is used as a competitive antagonist at mineralocorticoid receptors, which can contribute to its therapeutic effects in treating hypertension and related conditions.

Biological Activity

Orally active antihypertensive agent which displays a wide range of activities in vitro and in vivo . Inhibits L-, N- and T-type Ca 2+ channels. Also inhibits aldosterone-induced mineralocorticoid receptor activation. Exhibits cardioprotective and antiartherosclerotic effects.

Safety Profile

A poison by ingestion,intraperitoneal, and intravenous routes. When heated todecomposition it emits toxic vapors of NOx and HCl.

Upstream product

• 14813-01-5 1-benzyl-3-hydroxypiperidine 
• 74936-72-4 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid 
• 88712-56-5 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride 

Relevant articles and documents

BENIDIPINE HYDROCHLORIDE

Disclosed is a method for preparing benidipine hydrochloride, which comprising: 1) during the pre-treatment stage including acylchloridizing the main ring of dihydropyridine and then linking the side chain to synthesize directly benidipine hydrochloride, ultrasound technology is introduced, and the reactant material is dispersed and dissolved by untrasound to increase reaction rate; and/or 2) during the post-treatment stage, ultrasound technology is introduced and crude crystals or product obtained by heating to dryness of benidipine hydrochloride obtained via the method described above or any other synthetic routes is dissolved once more and then highly purified benidipine hydrochloride is obtained by untrasound.