194085-75-1

Basic information

• Product Name: 2-(2-CHLOROPHENYL)-2-HYDROXYETHYL CARBAMATE
• Synonyms: 2-(2-CHLOROPHENYL)-2-HYDROXYETHYL CARBAMATE;Carisbamate;(S)-Carisbamate;1,2-Ethanediol,1-(2-chlorophenyl)-, 2-carbaMate, (1S)-;JNJ 10234094;RWJ 333369;YKP 509;CarisbaMate (RWJ-333369)
• CAS NO: 194085-75-1
• Molecular Formula: C₉H₁₀ClNO₃
• Molecular Weight: 215.63
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals
• Mol File: 194085-75-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-(2-CHLOROPHENYL)-2-HYDROXYETHYL CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-CHLOROPHENYL)-2-HYDROXYETHYL CARBAMATE(194085-75-1)
• EPA Substance Registry System: 2-(2-CHLOROPHENYL)-2-HYDROXYETHYL CARBAMATE(194085-75-1)

Safety Data

• Hazardous Substances Data: 194085-75-1(Hazardous Substances Data)

Usage

Description

2-(2-CHLOROPHENYL)-2-HYDROXYETHYL CARBAMATE, also known as Carisbamate, is an antiepileptic agent that has been developed for the adjuvant treatment of partial onset epilepsy. It is effective in reducing spike and wave discharges in the frontoparietal cortex, increasing latency to the first running episode in convulsive seizures, and reducing motor seizure frequency in spontaneous seizures. Carisbamate also exhibits neuroprotective and antiepileptogenic properties in rodent epilepsy models. Its mechanism of action includes blocking Nav1.2 channels and inhibiting repetitive firing of action potentials in rat hippocampal neurons, as well as reducing T-type Ca2+ currents in HEK cells transfected with human recombinant Cav3.1 channels.

Uses

Used in Pharmaceutical Industry:
2-(2-CHLOROPHENYL)-2-HYDROXYETHYL CARBAMATE is used as an antiepileptic agent for the adjuvant treatment of partial onset epilepsy. It is effective in reducing spike and wave discharges, increasing latency to the first running episode in convulsive seizures, and reducing motor seizure frequency in spontaneous seizures due to its ability to block Nav1.2 channels, inhibit repetitive firing of action potentials, and reduce T-type Ca2+ currents.
Additionally, Carisbamate exhibits neuroprotective and antiepileptogenic properties, making it a promising candidate for further research and development in the treatment of epilepsy and potentially other neurological disorders.

Synthetic route

(S)-carbamic acid 2-(2-chloro-phenyl)-2-(1-methoxy-1-methyl-ethoxy)-ethyl ester (1026550-57-1) → carisbamate (194085-75-1)

Conditions	Yield
With sulfuric acid In water at 15 - 50℃; for 0.75 - 1.25h;

carisbamate (194085-75-1) + toluene-4-sulfonic acid (104-15-4) → (S)-(+)-2-(2-chlorophenyl)-2-hydroxy-ethyl carbamate p-toluenesulfonic acid (1027637-67-7)

Conditions	Yield
for 0.166667h; Product distribution / selectivity;
In hexane for 0.166667h; Product distribution / selectivity;

Upstream product

• 1026550-57-1 (S)-carbamic acid 2-(2-chloro-phenyl)-2-(1-methoxy-1-methyl-ethoxy)-ethyl ester 

Downstream Products

• 1027637-67-7 (S)-(+)-2-(2-chlorophenyl)-2-hydroxy-ethyl carbamate p-toluenesulfonic acid 

Relevant articles and documents

IMPROVED PROCESS FOR PREPARING 2-(SUBSTITUTED PHENYOL)-2-HYDROXY-ETHYL-CARBAMATES

The present invention relates to a process of preparing a compound of Formula I: Wherein R1 is defined in the specification. Compounds of Formula I are useful for treating disorders of the central nervous system, including epilepsy. The process includes a novel use of the reagent lithium borohydride.