Basic information
- CAS
533-45-9- Standard SMILES
Cc1ncsc1CCCl- InChIKey
PCLITLDOTJTVDJ-UHFFFAOYSA-N- Molecular formula
- C6H8ClNS
- Average molar mass
- 161.65 g/mol
- Monoisotopic mass
- 161.00659794
Overview
5-(2-chloroethyl)-4-methylthiazole is a member of thiazoles.
Names & identifiers
- Preferred name
- Clomethiazole
- IUPAC
- 5-(2-chloroethyl)-4-methyl-1,3-thiazole
- English name
- Clomethiazole
- Molecular formula
- C6H8ClNS
- Molecular weight
- 161.65
Names & synonyms
Show more names
Database identifiers
- CAS
533-45-9- PubChem CID
- 10783
- DTXSID
DTXSID6022842- ChEMBL
CHEMBL315795- ChEBI
CHEBI:92875- UNII
- 0C5DBZ19HV
- EC Number
- 208-565-7
- Nikkaji
- J6.328B
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 41.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 89.1
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
Pharmaceuticals -> Hypnotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals
Physicochemical properties
- Melting point
- 127 · 127-128 °C
- Boiling point
- 7 · bp7 92°
- Density
- 425 · d425 1.233
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 3.2 · pKa 3.2 (Uncertain)
- form
- Oil
- color
- Pale Yellow
- CAS DataBase Reference
- 533 · 533-45-9(CAS DataBase Reference)
- FDA UNII
- 0 C5DBZ19HV · 0C5DBZ19HV
- ATC code
- 5 CM02,N05CX04 · N05CM02,N05CX04
- NIST Chemistry Reference
- Clomethiazole(533-45-9)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 335 · H335-H302-H319-H412
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501-P273-P501
- HS Code
- 2934100090 · 2934100090
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
CLOMETHIAZOLE
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- hs_code
- 2934100090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H335-H302-H319-H412
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501-P273-P501
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of Action
clomethiazole interacts with the GABAA receptor complex. It inhibits the binding of [35S]butyl-bicyclophosphorothionate (TBPS), an effect indicative of GABAA receptor-channel activation, by increasing the rate of [35S]TBPS dissociation and decreasing the binding affinity. Gamma-aminobutyric acid (GABA), acting at GABAA receptors, is the main fast inhibitory neurotransmitter in mammalian central nervous system
MeSH Pharmacological Classification
Drugs used to prevent SEIZURES or reduce their severity.
Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.
Uses & manufacturing
Applications
UsesHypnotic.
UsesClomethiazolum is a drug which is structurally related to thiamine (vitamin B1) but acts like a sedative, hypnotic, muscle relaxant and anticonvulsant.
Upstream & downstream products
Upstream raw materials
Suppliers91 total
Additional notes
DefinitionChEBI: 5-(2-chloroethyl)-4-methylthiazole is a member of thiazoles.
Related reactions
Compound notes
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