Clemizole hydrochloride Chemical Properties
- Melting point:239-241°
- storage temp. 2-8°C
- solubility H2O: soluble2mg/mL, clear (warmed)
- form powder
- color white to beige
- Merck 14,2346
- CAS DataBase Reference1163-36-6(CAS DataBase Reference)
Clemizole hydrochloride Usage And Synthesis
- UsesClemizole is an antihistamine that antagonizes the histamine 1 receptor at high nanomolar concentrations. It less potently blocks transient receptor potential canonical channel 5 (TRPC5; IC50 = 1.0-1.3 μM), with at least 6-fold selectivity for TRPC5 over other TRP channels. Clemizole also has hepatitis C antiviral action through inhibition of NS4B function, showing synergy with boceprevir , and it inhibits seizures in a zebrafish model of Dravet Syndrome.
- Manufacturing ProcessFrom 13.1 g of N-p-chlorobenzyl-2-nitroaniline (MP 110°C, obtained in the
form of orange-red needles, from o-nitrochlorobenzene and pchlorobenzylamine by reaction for 3 hours at 150°C) by reduction with Raneynickel and hydrogen, in which reaction the substance may be suspended in
methanol or dissolved in methanol-ethyl acetate at normal pressure and at
about 40°C with combination of the theoretical quantity of hydrogen, 12.2 g
are obtained of o-amino-N-p-chlorobenzylaniline, which after recrystallization
from aqueous methanol has a MP of 90°C.
8 g of o-amino-N-p-chlorobenzylaniline and 2.8 g of pyridine are dissolved in dry ether and reacted with an ethereal solution of 3.9 g of chloracetyl chloride with cooling in a mixture of ice and common salt. 8 g of N-p-chlorobenzyl-N'- chloracetyl-o-phenylene diamine are obtained which can be worked up in the form of the crude product and, in the slightly colored form, has a MP of 130°C.
7.6 g of this compound are boiled with 3.9 g of pyrrolidine in 70 cc of toluene for some hours under reflux. After extraction by shaking with water and treatment with hydrochloric acid the hydrochloride is produced of N-pchlorobenzyl-N'-pyrrolidylacetyl-o-phenylene diamine together with some 1-pchlorobenzyl-2-N-pyrrolidylmethyl-benzimidazole. The former, after recrystallization from butanol, melts with foaming at 205°C, the latter, after recrystallization from butanol melts at 239°C to 241°C, and is in the form of white microscopic rods. Boiling in nitrobenzene converts the former compound into the latter.
- Therapeutic FunctionAntihistaminic
- N-Ethylbenzimidazole Clemizole hydrochloride 1-(1H-IMIDAZOL-2-YL)-N,N-DIMETHYLMETHANAMINE C-(1-BENZYL-1H-IMIDAZOL-2-YL)-METHYLAMINE 2HCL N-METHYL-N-[(1-METHYL-1H-BENZIMIDAZOL-2-YL)METHYL]AMINE N-Ethyl-2-methylbenzimidazole (1H-BENZOIMIDAZOL-2-YLMETHYL)-METHYL-AMINE 2-(AMINOMETHYL)-1-METHYLIMIDAZOLE 1-Benzylimidazole 1-METHYLBENZIMIDAZOLE 1-Benzyl-2-methyl-1H-imidazole 1-BENZYL-1H-BENZOIMIDAZOL-2-YL-METHYLAMINE DIHYDROCHLORIDE TIMTEC-BB SBB000240 Clemizole 2-AMINOMETHYLIMIDAZOLE HYDROCHLORIDE METHYL-(1-METHYL-1H-IMIDAZOL-2-YLMETHYL)-AMINE (1H-BENZO[D]IMIDAZOL-2-YL)METHANAMINE 1-(4-CHLOROBENZYL)-2-METHYLBENZIMIDAZOLE HCL
- Company Name:Shanghai JiYi Biotechnology Co. Ltd. Gold
- Company Name:Shanghai hongqu biomedical technology co. LTD Gold
- Company Name:BOC Sciences
- Company Name:Suzhou Guide Fine Material Co.Ltd.
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- Company Name:Shanghai T&W Pharmaceutical Co., Ltd.
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