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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
Structure of CHLORAL

SMILES

ClC(Cl)(Cl)C=O

InChI

InChIKey=HFFLGKNGCAIQMO-UHFFFAOYSA-N
InChI=1S/C2HCl3O/c3-2(4,5)1-6/h1H

HIDE SMILES / InChI

Description
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.

Originator

Sources: Proc. Physiol. Soc. 8-9. From: J. Chem. Soc., Abstr. 58, 1015-6 1890.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Somnote

Approved Use

Unknown
Primary
Somnote

Approved Use

Unknown
Primary
Somnote

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2993 ng/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
91.5 h
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
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
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

Doses

DosePopulationAdverse 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
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
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
Tachyarrhythmia
Ventricular extrasystoles
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
healthy, 67
n = 1
Health Status: healthy
Age Group: 67
Sex: M
Population Size: 1
Sources:
Tachyarrhythmia Disc. AE
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
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
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
healthy, 67
n = 1
Health Status: healthy
Age Group: 67
Sex: M
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Nicotine-induced Disturbances of Meiotic Maturation in Cultured Mouse Oocytes: Alterations of Spindle Integrity and Chromosome Alignment.
2004 Sep 15
The history of barbiturates a century after their clinical introduction.
2005 Dec
The role of serendipity in drug discovery.
2006
Environmental contaminant trichloroethylene promotes autoimmune disease and inhibits T-cell apoptosis in MRL(+/+) mice.
2006 Dec 1
Ability of trichloroethylene metabolite to promote immune pathology is strain-specific.
2006 Dec 1
Occurrence of a new generation of disinfection byproducts.
2006 Dec 1
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
Degradation of disinfection byproducts by carbonate green rust.
2007 Mar 1
Effect of age and sedative agent on the accuracy of bispectral index in detecting depth of sedation in children.
2007 Sep
Early experience with remote pressure sensor respiratory plethysmography monitoring sedation in the MR scanner.
2007 Sep
Sleep disorders in children.
2007 Sep 1
Neuroanatomical pattern of mitochondrial complex I pathology varies between schizophrenia, bipolar disorder and major depression.
2008
Anxiety in children undergoing VCUG: sedation or no sedation?
2008
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
Acid-catalysed rearrangement of glycosyl trichloroacetimidates: a novel route to glycosylamines.
2008 Feb 4
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
A model of ischemia-induced neuroblast activation in the adult subventricular zone.
2009
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
Catalytic asymmetric synthesis of beta-sultams as precursors for taurine derivatives.
2009 Aug 17
Arabidopsis CULLIN3 genes regulate primary root growth and patterning by ethylene-dependent and -independent mechanisms.
2009 Jan
Theoretical investigation of N-nitrosodimethylamine formation from dimethylamine nitrosation catalyzed by carbonyl compounds.
2009 Jan 29
Phlebotomus (Euphlebotomus) barguesae n. sp. from Thailand (Diptera - Psychodidae).
2009 Jan 8
Formation of chlorinated disinfection by-products in viticulture.
2009 Jul
Sedation of neonates with chloral.
2009 Jun
Natural history, clinical pattern, and surgical considerations of pneumatosis intestinalis.
2009 Jun 18
Evidence of autoimmune-related effects of trichloroethylene exposure from studies in mice and humans.
2009 May
A clearer view of TCE: evidence supports autoimmune link.
2009 May
A submarine journey: the pyrrole-imidazole alkaloids.
2009 Nov 27
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
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
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
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
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
Patents

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
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.
Name Type Language
CHLORAL
HSDB  
Systematic Name English
2,2,2-TRICHLOROACETALDEHYDE
Systematic Name English
CHLORAL [HSDB]
Common Name English
TRICHLOROETHANAL
Systematic Name English
ACETALDEHYDE, TRICHLORO-
Systematic Name English
TRICHLOROACETALDEHYDE
MI  
Systematic Name English
TRICHLOROACETALDEHYD
Systematic Name English
TRICHLOROACETALDEHYDE [MI]
Common Name English
CHLORAL [IARC]
Common Name English
Classification Tree Code System Code
IARC Chloral
NCI_THESAURUS C29756
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
Code System Code Type Description
PUBCHEM
6407
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
MESH
C021100
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-911-5
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
HSDB
2557
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
CHEBI
48814
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
WIKIPEDIA
CHLORAL
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
NCI_THESAURUS
C76937
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
FDA UNII
FLI06WS32H
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
CAS
75-87-6
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
EPA CompTox
DTXSID7024744
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
RXCUI
38574
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY RxNorm
DRUG BANK
DB02650
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY
MERCK INDEX
M11061
Created by admin on Fri Dec 16 20:30:48 UTC 2022 , Edited by admin on Fri Dec 16 20:30:48 UTC 2022
PRIMARY Merck Index