U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
Doses

Doses

DosePopulationAdverse events​
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 0.67
Health Status: healthy
Age Group: 0.67
Sex: M
Sources:
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
Health Status: healthy
Age Group: 4
Sex: F
Sources:
Disc. AE: Cardiopulmonary arrest...
AEs leading to
discontinuation/dose reduction:
Cardiopulmonary arrest (grade 5)
Sources:
30 g single, oral
Overdose
Dose: 30 g
Route: oral
Route: single
Dose: 30 g
Sources:
healthy, 67
Health Status: healthy
Age Group: 67
Sex: F
Sources:
Disc. AE: Ventricular tachycardia...
AEs leading to
discontinuation/dose reduction:
Ventricular tachycardia
Sources:
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
healthy, 67
Health Status: healthy
Age Group: 67
Sex: M
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:
healthy, 0.67
Health Status: healthy
Age Group: 0.67
Sex: M
Sources:
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
Health Status: healthy
Age Group: 4
Sex: F
Sources:
Ventricular tachycardia Disc. AE
30 g single, oral
Overdose
Dose: 30 g
Route: oral
Route: single
Dose: 30 g
Sources:
healthy, 67
Health Status: healthy
Age Group: 67
Sex: F
Sources:
Cardiac arrhythmia Disc. AE
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
healthy, 67
Health Status: healthy
Age Group: 67
Sex: M
Sources:
Tachyarrhythmia Disc. AE
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
healthy, 67
Health Status: healthy
Age Group: 67
Sex: M
Sources:
Ventricular extrasystoles Disc. AE
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
healthy, 67
Health Status: healthy
Age Group: 67
Sex: M
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
The role of serendipity in drug discovery.
2006
Occurrence of a new generation of disinfection byproducts.
2006 Dec 1
Nocturnal sedation in a child with facial ulceration.
2006 Jun
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
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
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
TRICHLOROACETALDEHYDE
MI  
Preferred Name English
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
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 Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
Code System Code Type Description
PUBCHEM
6407
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
DAILYMED
FLI06WS32H
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
MESH
C021100
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-911-5
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
HSDB
2557
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
CHEBI
48814
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
WIKIPEDIA
CHLORAL
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
NCI_THESAURUS
C76937
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
FDA UNII
FLI06WS32H
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
CAS
75-87-6
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID7024744
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
RXCUI
38574
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB02650
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY
MERCK INDEX
m11061
Created by admin on Mon Mar 31 18:31:32 GMT 2025 , Edited by admin on Mon Mar 31 18:31:32 GMT 2025
PRIMARY Merck Index