Details
Stereochemistry | ACHIRAL |
Molecular Formula | C2HCl3O |
Molecular Weight | 147.388 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC(Cl)(Cl)C=O
InChI
InChIKey=HFFLGKNGCAIQMO-UHFFFAOYSA-N
InChI=1S/C2HCl3O/c3-2(4,5)1-6/h1H
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/29099542 | https://www.ncbi.nlm.nih.gov/pubmed/28242616 | https://www.ncbi.nlm.nih.gov/pubmed/27941708
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/29099542 | https://www.ncbi.nlm.nih.gov/pubmed/28242616 | https://www.ncbi.nlm.nih.gov/pubmed/27941708
Chloral is a chlorinated aldehyde that found extensive use, beginning in the 1940s, as a precursor in the production of the insecticide DDT and, to a lesser extent, of other insecticides and pharmaceuticals. This use of chloral has declined steadily since the 1960s, especially in those countries where the use of DDT has been restricted. Chloral is readily converted to chloral hydrate in the presence of water. Chloral hydrate is used as a sedative before medical procedures and to reduce anxiety related to withdrawal from drugs. Wider exposure to chloral hydrate occurs at microgram-per-liter levels in drinking water and swimming pools as a result of chlorination. Chloral hydrate is a well-established aneuploidogenic agent that also has some mutagenic activity. In human cells in vitro, chloral hydrate induced aneuploidy, micronuclei and gene mutations. Chloral hydrate clearly induced micronuclei in Chinese hamster cells, whereas findings in mouse lymphoma cells were conflicting. Induction of somatic mutation (but not sex-linked mutation) by chloral hydrate was demonstrated in insects. Chloral hydrate is metabolized in vivo to trichloroethanol, which is responsible for its physiological and psychological effects. The metabolite of chloral hydrate exerts its pharmacological properties via enhancing the GABA receptor complex and therefore is similar in action to benzodiazepines, nonbenzodiazepines, and barbiturates. In clinical studies, oral chloral hydrate appears to have a lower sedation failure rate when compared with oral promethazine for children undergoing pediatric neurodiagnostic procedures. The sedation failure was similar for other comparisons such as oral dexmedetomidine, oral hydroxyzine hydrochloride, and oral midazolam. When compared with intravenous pentobarbital and music therapy, oral chloral hydrate had a higher sedation failure rate. Compared to dexmedetomidine, chloral hydrate was associated with a higher risk of nausea and vomiting.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17557503 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Somnote Approved UseUnknown |
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Primary | Somnote Approved UseUnknown |
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Primary | Somnote Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2993 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9522024/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
2,2,2-TRICHLOROETHANOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6131 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9522024/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
2,2,2-TRICHLOROETHANOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
91.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9522024/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRICHLOROACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9522024/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
2,2,2-TRICHLOROETHANOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9522024/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
2,2,2-TRICHLOROETHANOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Sources: Page: p.235 |
healthy, 0.67 n = 1 Health Status: healthy Age Group: 0.67 Sex: M Population Size: 1 Sources: Page: p.235 |
Disc. AE: Loss of consciousness... AEs leading to discontinuation/dose reduction: Loss of consciousness Sources: Page: p.235 |
70 mg/kg single, oral Recommended Dose: 70 mg/kg Route: oral Route: single Dose: 70 mg/kg Sources: Page: p.220 |
healthy, 4 n = 1 Health Status: healthy Condition: Sedation Age Group: 4 Sex: F Population Size: 1 Sources: Page: p.220 |
Disc. AE: Cardiopulmonary arrest... AEs leading to discontinuation/dose reduction: Cardiopulmonary arrest (grade 5) Sources: Page: p.220 |
30 g single, oral Overdose Dose: 30 g Route: oral Route: single Dose: 30 g Sources: Page: p.232 |
healthy, 67 n = 1 Health Status: healthy Age Group: 67 Sex: F Population Size: 1 Sources: Page: p.232 |
Disc. AE: Ventricular tachycardia... AEs leading to discontinuation/dose reduction: Ventricular tachycardia Sources: Page: p.232 |
5 g single, oral Overdose |
healthy, 67 n = 1 Health Status: healthy Age Group: 67 Sex: M Population Size: 1 Sources: |
Disc. AE: Cardiac arrhythmia, Tachyarrhythmia... AEs leading to discontinuation/dose reduction: Cardiac arrhythmia Sources: Tachyarrhythmia Ventricular extrasystoles |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Loss of consciousness | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Sources: Page: p.235 |
healthy, 0.67 n = 1 Health Status: healthy Age Group: 0.67 Sex: M Population Size: 1 Sources: Page: p.235 |
Cardiopulmonary arrest | grade 5 Disc. AE |
70 mg/kg single, oral Recommended Dose: 70 mg/kg Route: oral Route: single Dose: 70 mg/kg Sources: Page: p.220 |
healthy, 4 n = 1 Health Status: healthy Condition: Sedation Age Group: 4 Sex: F Population Size: 1 Sources: Page: p.220 |
Ventricular tachycardia | Disc. AE | 30 g single, oral Overdose Dose: 30 g Route: oral Route: single Dose: 30 g Sources: Page: p.232 |
healthy, 67 n = 1 Health Status: healthy Age Group: 67 Sex: F Population Size: 1 Sources: Page: p.232 |
Cardiac arrhythmia | Disc. AE | 5 g single, oral Overdose |
healthy, 67 n = 1 Health Status: healthy Age Group: 67 Sex: M Population Size: 1 Sources: |
Tachyarrhythmia | Disc. AE | 5 g single, oral Overdose |
healthy, 67 n = 1 Health Status: healthy Age Group: 67 Sex: M Population Size: 1 Sources: |
Ventricular extrasystoles | Disc. AE | 5 g single, oral Overdose |
healthy, 67 n = 1 Health Status: healthy Age Group: 67 Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Nicotine-induced Disturbances of Meiotic Maturation in Cultured Mouse Oocytes: Alterations of Spindle Integrity and Chromosome Alignment. | 2004 Sep 15 |
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The history of barbiturates a century after their clinical introduction. | 2005 Dec |
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The role of serendipity in drug discovery. | 2006 |
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Environmental contaminant trichloroethylene promotes autoimmune disease and inhibits T-cell apoptosis in MRL(+/+) mice. | 2006 Dec 1 |
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Ability of trichloroethylene metabolite to promote immune pathology is strain-specific. | 2006 Dec 1 |
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Occurrence of a new generation of disinfection byproducts. | 2006 Dec 1 |
|
Eszopiclone: its use in the treatment of insomnia. | 2007 Aug |
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Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides. | 2007 Dec 7 |
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Degradation of disinfection byproducts by carbonate green rust. | 2007 Mar 1 |
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Effect of age and sedative agent on the accuracy of bispectral index in detecting depth of sedation in children. | 2007 Sep |
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Early experience with remote pressure sensor respiratory plethysmography monitoring sedation in the MR scanner. | 2007 Sep |
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Sleep disorders in children. | 2007 Sep 1 |
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Neuroanatomical pattern of mitochondrial complex I pathology varies between schizophrenia, bipolar disorder and major depression. | 2008 |
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Anxiety in children undergoing VCUG: sedation or no sedation? | 2008 |
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Dr Smellie's prescriptions for pregnant women. | 2008 Apr |
|
Effects of a high fat diet on bone of growing rats. Correlations between visceral fat, adiponectin and bone mass density. | 2008 Apr 28 |
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Acid-catalysed rearrangement of glycosyl trichloroacetimidates: a novel route to glycosylamines. | 2008 Feb 4 |
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Mechanistics of trichloroethylene mineralization by the white-rot fungus Trametes versicolor. | 2008 Jan |
|
Recent advances and opportunities in research on lupus: environmental influences and mechanisms of disease. | 2008 Jun |
|
Insight into the early steps of root hair formation revealed by the procuste1 cellulose synthase mutant of Arabidopsis thaliana. | 2008 May 16 |
|
Persistent inflammation alters the function of the endogenous brain stem cell compartment. | 2008 Oct |
|
Evidence for involvement of calcitonin gene-related peptide in nitroglycerin response and association with mitochondrial aldehyde dehydrogenase-2 (ALDH2) Glu504Lys polymorphism. | 2008 Sep 9 |
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A model of ischemia-induced neuroblast activation in the adult subventricular zone. | 2009 |
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Differentiation of rabbit bone marrow mesenchymal stem cells into corneal epithelial cells in vivo and ex vivo. | 2009 |
|
Loss of surface N-methyl-D-aspartate receptor proteins in mouse cortical neurones during anaesthesia induced by chloral hydrate in vivo. | 2009 Apr |
|
Efficient synthesis of six tri- to hexasaccharide fragments of Shigella flexneri serotypes 3a and/or X O-antigen, including a study on acceptors containing N-trichloroacetylglucosamine versus N-acetylglucosamine. | 2009 Apr 3 |
|
Disinfection byproduct formation and fractionation behavior of natural organic matter surrogates. | 2009 Aug 1 |
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Catalytic asymmetric synthesis of beta-sultams as precursors for taurine derivatives. | 2009 Aug 17 |
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Arabidopsis CULLIN3 genes regulate primary root growth and patterning by ethylene-dependent and -independent mechanisms. | 2009 Jan |
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Theoretical investigation of N-nitrosodimethylamine formation from dimethylamine nitrosation catalyzed by carbonyl compounds. | 2009 Jan 29 |
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Phlebotomus (Euphlebotomus) barguesae n. sp. from Thailand (Diptera - Psychodidae). | 2009 Jan 8 |
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Formation of chlorinated disinfection by-products in viticulture. | 2009 Jul |
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Sedation of neonates with chloral. | 2009 Jun |
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Natural history, clinical pattern, and surgical considerations of pneumatosis intestinalis. | 2009 Jun 18 |
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Evidence of autoimmune-related effects of trichloroethylene exposure from studies in mice and humans. | 2009 May |
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A clearer view of TCE: evidence supports autoimmune link. | 2009 May |
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A submarine journey: the pyrrole-imidazole alkaloids. | 2009 Nov 27 |
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Alterations of nocturnal activity in rats following subchronic oral administration of the neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline. | 2009 Oct |
|
Chemical synthesis of a hyaluronic acid decasaccharide. | 2009 Oct 16 |
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Tissue-specific remodeling of the mitochondrial proteome in type 1 diabetic akita mice. | 2009 Sep |
|
Professional skills and competence for safe and effective procedural sedation in children: recommendations based on a systematic review of the literature. | 2010 |
|
Phosphorylation of conserved PIN motifs directs Arabidopsis PIN1 polarity and auxin transport. | 2010 Apr |
|
TRAUCO, a Trithorax-group gene homologue, is required for early embryogenesis in Arabidopsis thaliana. | 2010 Feb |
|
Further studies on the phlebotomine sandflies of the kala-azar endemic lowlands of Humera-Metema (north-west Ethiopia) with observations on their natural blood meal sources. | 2010 Feb 3 |
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Procedural sedation analgesia. | 2010 Jan |
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Obstructive sleep apnoea syndrome in children and anaesthesia. | 2010 Jan |
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O-Silylated C3-halohydrins as a novel class of protected building blocks for total, regio- and stereocontrolled synthesis of glycerolipid frameworks. | 2010 Jan 21 |
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Auxin polar transport is essential for the development of zygote and embryo in Nicotiana tabacum L. and correlated with ABP1 and PM H+-ATPase activities. | 2010 Jun |
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Methodological problems in determining TCAA in soils-the discovery of novel natural trichloroacetyl containing compounds and their interference with a common method for determining TCAA in soil and vegetation. | 2010 Mar |
|
Generating a generation of proteasome inhibitors: from microbial fermentation to total synthesis of salinosporamide a (marizomib) and other salinosporamides. | 2010 Mar 25 |
Sample Use Guides
Oral: 50 mg/kg or 1.5 g/m up to a maximum single dose of 1 g.
Rectal: 18 mg/kg (325 mg/18 kg) once daily before bedtime.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27941708
RAW264.7 macrophages were cultured with IMDM medium containing 10% fetal bovine serum, and then treated with different concentrations of chloral hydrate with final concentration
of 0, 0.25, 0.5, 1.0, and 2.0 mg/ml for 3 h, and we observed
the morphologic changes under the light microscope. RAW264.7 macrophages were treated with chloral hydrate at 0.5 mg/ml for different times (1, 3, 5, and 7 h), and we observed
the morphologic changes.
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Classification Tree | Code System | Code | ||
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IARC | Chloral | ||
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NCI_THESAURUS |
C29756
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6407
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C021100
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200-911-5
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2557
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48814
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CHLORAL
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C76937
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FLI06WS32H
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75-87-6
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DTXSID7024744
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38574
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DB02650
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M11061
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PRIMARY | Merck Index |
ACTIVE MOIETY