Clomethiazole Chemical Properties

Melting point:

127-128 °C

Boiling point:

bp7 92°

Density 

d425 1.233

refractive index 

1.6000 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

pKa 3.2 (Uncertain)

form 

Oil

color 

Pale Yellow

CAS DataBase Reference

533-45-9(CAS DataBase Reference)

NIST Chemistry Reference

Clomethiazole(533-45-9)

Safety Information

HS Code 

2934100090

Clomethiazole Usage And Synthesis

Uses

Hypnotic.

Uses

Clomethiazolum is a drug which is structurally related to thiamine (vitamin B1) but acts like a sedative, hypnotic, muscle relaxant and anticonvulsant.

Definition

ChEBI: 5-(2-chloroethyl)-4-methylthiazole is a member of thiazoles.

brand name

Clomiazin;Distraneurine;Emineurina;Gebriazol;Hemineurine;Heminevrin;Somnevrin.

World Health Organization (WHO)

Clomethiazole, which has sedative, anxiolytic and anticonvulsant activity, was introduced in 1960 for the treatment of acute alcohol withdrawal, delirium tremens, status epilepticus, eclamptic toxaemia, sleep disturbances in the elderly and agitation in psychogeriatic patients. It is also used as a sedative in certain anaesthetic procedures. There is little evidence of primary dependence in man but secondary dependence can occur in patients with a history of abuse of other substances, particularly alcohol. Dependence of this type has been reported as a result of inappropriate, long-term prescribing to outpatient alcoholics. Clomethiazole should not be prescribed to alcoholics who continue to drink. Adverse interactions with alcohol have been fatal. Although not controlled under the 1971 Convention on Psychotropic Substances, clomethiazole is subject to analogous controls in some countries.

Biological Activity

Sedative and anticonvulsant which is neuroprotective in a number of animal models. Prevents the degeneration of serotonergic nerve terminals induced by MDMA ('Ecstasy').

Synthesis

The general procedure for the synthesis of 5-(2-chloroethyl)-4-methylthiazole from 4-methyl-5-hydroxyethylthiazole was as follows: referring to Example 18, 2-(4-methylthiazol-5-yl)ethanol (500 mg, 3.49 mmol) was dissolved in thionyl chloride (4 mL). The reaction mixture was stirred under reflux conditions for 3 hours. After completion of the reaction, the mixture was concentrated to dryness to give a light yellow solid product (680 mg, yield: 98%). The product was analyzed by ESI-MS and showed m/z: 162.0 [M + H]+.

References

[1] Patent: US2017/158680, 2017, A1. Location in patent: Paragraph 0385
[2] Journal of the American Chemical Society, 2001, vol. 123, # 6, p. 1017 - 1022
[3] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 12, p. 658 - 660
[4] Journal of the American Chemical Society, 1982, vol. 104, # 18, p. 4934 - 4943
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 5988 - 6003

Clomethiazole(533-45-9)Related Product Information

• Thiazole
• 2-Butanone oxime
• 4-Methylthiazole
• 2,2'-Dithiobis(benzothiazole)
• Methyl 2-hydroxyethyl cellulose
• DIETHYLALUMINUM CHLORIDE
• 2-Methyl-4-isothiazolin-3-one
• Benzothiazole
• Fosthiazate
• Methylchloroisothiazolinone/methylisothiazolinone mixture (MCIT/MIT)
• 2-Butanone
• CLOMETHIAZOLE EDISILATE
• BECLOTIAMINE
• Clomethiazole ethanedisulfonate,clomethiazole ethane-1,2-disulfonate,clomethiazole edisylate
• Clomethiazole
• METHYL ETHYLCELLULOSE
• 2,2,2-TRICHLORO-1-[2-(DIMETHYLAMINO)-4-METHYL-1,3-THIAZOL-5-YL]ETHANONE
• 5-(2-Chloroethyl)-4-methyl-2-phenylthiazole ethanedisulfonate (2:1)