58934-46-6

Basic information

• Product Name: N-(4-chlorophenyl)-N-(1-isopropyl-4-piperidyl)phenylacetamide monohydrochloride
• Synonyms: N-(4-chlorophenyl)-N-(1-isopropyl-4-piperidyl)phenylacetamide monohydrochloride;LORCAINIDE HYDROCHLORIDE;Isocainide hydrochloride;4'-Chloro-N-(1-isopropyl-4-piperidyl)-2-phenylacetanilide monohydrochloride;Benzeneacetamide, N-(4-chlorophenyl)-N-[1-(1-methylethyl)-4-piperidinyl]-, monohydrochloride;Nsc310411
• CAS NO: 58934-46-6
• Molecular Formula: C22H28Cl2N2O
• Molecular Weight: 407.37652
• EINECS: 261-504-6
• Mol File: 58934-46-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 263°
• Boiling Point: 503°C at 760 mmHg
• Flash Point: 258°C
• Appearance: /
• Vapor Pressure: 3.01E-10mmHg at 25°C
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to 20 mg/ml), in Water (up to 20 mg/ml), or in Ethanol (up to 20 mg/ml).
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO, distilled water or ethanol may be stored at -20°C for up to 1 month
• CAS DataBase Reference: N-(4-chlorophenyl)-N-(1-isopropyl-4-piperidyl)phenylacetamide monohydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-chlorophenyl)-N-(1-isopropyl-4-piperidyl)phenylacetamide monohydrochloride(58934-46-6)
• EPA Substance Registry System: N-(4-chlorophenyl)-N-(1-isopropyl-4-piperidyl)phenylacetamide monohydrochloride(58934-46-6)

Safety Data

• Hazardous Substances Data: 58934-46-6(Hazardous Substances Data)

Usage

Description

N-(4-chlorophenyl)-N-(1-isopropyl-4-piperidyl)phenylacetamide monohydrochloride, also known as Lorcainide hydrochloride, is a voltage-gated Na+ channel blocker with the chemical formula C22H26ClN3O and a molecular weight of 390.01 g/mol. It is a white crystalline powder that is soluble in water and has a melting point of 198-200°C. Lorcainide hydrochloride is known for its ability to protect murine cultured cortical neurons from injury induced by oxygen-glucose deprivation and acts at the ouabain binding site of guinea pig cardiac Na+/K+ ATPase, inhibiting the enzyme with an IC50 of 34 μM.

Uses

Used in Pharmaceutical Industry:
Lorcainide hydrochloride is used as a cardiac depressant for the treatment of arrhythmias. It works by blocking the voltage-gated Na+ channels, which slows down the rate of depolarization and prolongs the refractory period of cardiac cells. This action helps to restore normal heart rhythm and prevent the occurrence of abnormal heart beats.
Used in Research Applications:
Lorcainide hydrochloride is also used as a research tool in the study of ion channels and their role in various physiological and pathological processes. It can be used to investigate the mechanisms of action of other Na+ channel blockers and to explore the potential therapeutic applications of these compounds in the treatment of various diseases, such as epilepsy, neuropathic pain, and certain types of cancer.

References

1) Sheldon?et al.?(1989),?Antiarrhythmic drugs and the cardiac sodium channel: current models; Clin. Chem.,?35?748 2) Lynch?et al.?(1995),?Sodium channel clockers reduce oxygen-glucose deprivation-induced cortical neuronal injury when combined with glutamate receptor antagonists; J. Pharmacol. Exp. Ther.,?273?554 3) Almotrefi?et al. (1999),?Class I antiarrhythmic drug effects on ouabain binding to guinea pig cardiac Na+ -K+ ATPase; Can. J. Physiol. Pharmacol.,?77?866

InChI:InChI=1/C22H27ClN2O.ClH/c1-17(2)24-14-12-21(13-15-24)25(20-10-8-19(23)9-11-20)22(26)16-18-6-4-3-5-7-18;/h3-11,17,21H,12-16H2,1-2H3;1H

Upstream product

• 63260-75-3 N-(4-chloro-phenyl)-2-phenyl-N-piperidin-4-yl-acetamide 
• 75-26-3 isopropyl bromide 

Relevant articles and documents

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Novel N-aryl-N-(1-L-4-piperidinyl)arylacetamides useful as anti-arrhythmic agents, a method of treating arrhythmia which comprises the systemic administration of such compounds to warm-blooded animals and pharmaceutical compositions to be used therefor.