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 |
---|---|---|---|---|
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 |
---|---|---|---|---|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
8 g single, oral Overdose |
healthy, 0.67 |
Disc. AE: Loss of consciousness... AEs leading to discontinuation/dose reduction: Loss of consciousness Sources: |
70 mg/kg single, oral Recommended Dose: 70 mg/kg Route: oral Route: single Dose: 70 mg/kg Sources: |
healthy, 4 |
Disc. AE: Cardiopulmonary arrest... AEs leading to discontinuation/dose reduction: Cardiopulmonary arrest (grade 5) Sources: |
30 g single, oral Overdose |
healthy, 67 |
Disc. AE: Ventricular tachycardia... AEs leading to discontinuation/dose reduction: Ventricular tachycardia Sources: |
5 g single, oral Overdose |
healthy, 67 |
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 |
healthy, 0.67 |
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: |
healthy, 4 |
Ventricular tachycardia | Disc. AE | 30 g single, oral Overdose |
healthy, 67 |
Cardiac arrhythmia | Disc. AE | 5 g single, oral Overdose |
healthy, 67 |
Tachyarrhythmia | Disc. AE | 5 g single, oral Overdose |
healthy, 67 |
Ventricular extrasystoles | Disc. AE | 5 g single, oral Overdose |
healthy, 67 |
PubMed
Title | Date | PubMed |
---|---|---|
Catalysis of dehydrogenation of 4-trans-(N,N-dimethylamino)cinnamaldehyde by aldehyde dehydrogenase. | 2001 Jan 30 |
|
Tetrachloroethylene oxide: hydrolytic products and reactions with phosphate and lysine. | 2002 Aug |
|
Guinea pig maximization test for trichloroethylene and its metabolites. | 2002 Jun |
|
Trichloroethanol alters action potentials in a subgroup of primary sensory neurones. | 2002 May 7 |
|
The endogeneous formation of highly chlorinated tetrahydro-beta-carbolines as a possible causative mechanism in idiopathic Parkinson's disease. | 2003 |
|
Asymmetric synthesis of the highly potent anti-metastatic prostacyclin analogue cicaprost and its isomer isocicaprost. | 2003 Aug 13 |
|
[Anhydride and halogenated-anhydride trihalogenacetic acid interaction with thymidine-5'-phosphate: ways to new activating reagents in nucleotide phosphorylation reactions]. | 2003 Jan-Feb |
|
Identification of trichloroethylene and its metabolites in human seminal fluid of workers exposed to trichloroethylene. | 2003 Mar |
|
Some drinking-water disinfectants and contaminants, including arsenic. Monographs on chloramine, chloral and chloral hydrate, dichloroacetic acid, trichloroacetic acid and 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone. | 2004 |
|
The effect of fasting practice on sedation with chloral hydrate. | 2004 Dec |
|
Tricyclic furanoid dichloroacetyl orthoesters of D-mannose from 1,2-O-trichloroethylidene-beta-D-mannofuranose. | 2004 Jul 12 |
|
Activation and attenuation of apoptosis of CD4+ T cells following in vivo exposure to two common environmental toxicants, trichloroacetaldehyde hydrate and trichloroacetic acid. | 2004 Nov |
|
Meerwein-Ponndorf-Verley alkynylation of aldehydes: essential modification of aluminium alkoxides for rate acceleration and asymmetric synthesis. | 2004 Nov 21 |
|
[Healing activity of methanolic extract of the barks of Spathodea campanulata Beauv (Bignoniaceae) in rat experimental burn model]. | 2005 |
|
Characterization of hyperinsulinism in infancy assessed with PET and 18F-fluoro-L-DOPA. | 2005 Apr |
|
The effect of chloral hydrate on the in-vitro T3 binding to adult rat cerebral nuclei. | 2005 Aug |
|
Analysis of an interaction threshold in a mixture of drugs and/or chemicals. | 2005 Aug 30 |
|
Pharmacodynamics of chloral hydrate in former preterm infants. | 2005 Jul |
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The role of serendipity in drug discovery. | 2006 |
|
Occurrence of a new generation of disinfection byproducts. | 2006 Dec 1 |
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Nocturnal sedation in a child with facial ulceration. | 2006 Jun |
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Eszopiclone: its use in the treatment of insomnia. | 2007 Aug |
|
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 |
|
Chronic exposure to a trichloroethylene metabolite in autoimmune-prone MRL+/+ mice promotes immune modulation and alopecia. | 2007 Feb |
|
Early experience with remote pressure sensor respiratory plethysmography monitoring sedation in the MR scanner. | 2007 Sep |
|
Neuroanatomical pattern of mitochondrial complex I pathology varies between schizophrenia, bipolar disorder and major depression. | 2008 |
|
Dr Smellie's prescriptions for pregnant women. | 2008 Apr |
|
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 |
|
Arabidopsis CULLIN3 genes regulate primary root growth and patterning by ethylene-dependent and -independent mechanisms. | 2009 Jan |
|
Phlebotomus (Euphlebotomus) barguesae n. sp. from Thailand (Diptera - Psychodidae). | 2009 Jan 8 |
|
Natural history, clinical pattern, and surgical considerations of pneumatosis intestinalis. | 2009 Jun 18 |
|
Tissue-specific remodeling of the mitochondrial proteome in type 1 diabetic akita mice. | 2009 Sep |
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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 |
|
Procedural sedation analgesia. | 2010 Jan |
|
Obstructive sleep apnoea syndrome in children and anaesthesia. | 2010 Jan |
|
O-Silylated C3-halohydrins as a novel class of protected building blocks for total, regio- and stereocontrolled synthesis of glycerolipid frameworks. | 2010 Jan 21 |
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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FLI06WS32H
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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