Clomethiazole

HCID 10783

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

Clomethiazole533-45-9Chlormethiazole5-(2-CHLOROETHYL)-4-METHYLTHIAZOLEClomethiazolum5-(2-Chloroethyl)-4-methyl-1,3-thiazoleClometiazolThiazole, 5-(2-chloroethyl)-4-methyl-ClometiazoloDistraneurineDTXSID60228420C5DBZ19HV
Show more names
ChlorethiazoleClomethiazole 98%ChlormethiazoleHClCLOMETHIAZOLE HCLClomethiazole in methanolClomethiazole, 10 mM in DMSO
DTXCID802842clomAtiazoleRefChem:388876N05CM02208-565-7DistraneurinEmineurinaChlorethiazol

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

Experimental & physicochemical properties

Drugs · 5 items

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)

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 4 items

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 · 2 items

N - Nervous system

QN - Nervous system

Mechanism of Action · 1 item

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

Metabolism/MetabolitesClomethiazole has known human metabolites that include NLA-715.
MeSH Pharmacological Classification · 4 items

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

UsesUse (kg; approx.) in Germany (2009): >2500

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

Suppliers91 total

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]

Additional notes

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

Related reactions

3 records

Compound notes

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