U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Catalysis of dehydrogenation of 4-trans-(N,N-dimethylamino)cinnamaldehyde by aldehyde dehydrogenase.
2001 Jan 30
Antiparallel pleated beta-sheets observed in crystal structures of N,N-bis(trichloroacetyl) and N,N-bis(m-bromobenzoyl) gramicidin S.
2001 Nov 1
Toxicology and carcinogenesis study of chloral hydrate (ad libitum and dietary controlled) (CAS no. 302-17-0) in male B6C3F1 mice (gavage study).
2002 Dec
Degradation pathways of trichloroethylene and 1,1,1-trichloroethane by Mycobacterium sp. TA27.
2002 Feb
Endogenous alkaloids in man. XXXVIII. "Chiral" and "achiral" determination of the neurotoxin TaClo (1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline) from blood and urine samples by high-performance liquid chromatography--electrospray ionization tandem mass spectrometry.
2002 Feb 15
Expression of functional mammalian P450 2E1 in hairy root cultures.
2002 Feb 15
Highly accelerating effect of lewis acids on ruthenium(II)-catalyzed radical addition reactions.
2002 Mar
Trichloroethanol alters action potentials in a subgroup of primary sensory neurones.
2002 May 7
Toward the automated solid-phase synthesis of oligoglucosamines: systematic evaluation of glycosyl phosphate and glycosyl trichloroacetimidate building blocks.
2002 Nov 19
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
Analysis of an interaction threshold in a mixture of drugs and/or chemicals.
2005 Aug 30
Synthesis of radiolabelled 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline (TaClo), a neurotoxic chloral-derived mammalian alkaloid, and its biodistribution in rats.
2006 Aug
Environmental contaminant trichloroethylene promotes autoimmune disease and inhibits T-cell apoptosis in MRL(+/+) mice.
2006 Dec 1
[Study on decomposed products of trichlorfon in process of gas chromatographic analysis by mass spectrometry].
2006 Jan
Memory trace of motor learning shifts transsynaptically from cerebellar cortex to nuclei for consolidation.
2006 May 12
Key issues in the modes of action and effects of trichloroethylene metabolites for liver and kidney tumorigenesis.
2006 Sep
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
Effect of age and sedative agent on the accuracy of bispectral index in detecting depth of sedation in children.
2007 Sep
Sleep disorders in children.
2007 Sep 1
Anxiety in children undergoing VCUG: sedation or no sedation?
2008
Effects of a high fat diet on bone of growing rats. Correlations between visceral fat, adiponectin and bone mass density.
2008 Apr 28
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
Formation of chlorinated disinfection by-products in viticulture.
2009 Jul
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
Chemical synthesis of a hyaluronic acid decasaccharide.
2009 Oct 16
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
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 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
Code System Code Type Description
PUBCHEM
6407
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
DAILYMED
FLI06WS32H
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
MESH
C021100
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-911-5
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
HSDB
2557
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
CHEBI
48814
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
WIKIPEDIA
CHLORAL
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
NCI_THESAURUS
C76937
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
FDA UNII
FLI06WS32H
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
CAS
75-87-6
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID7024744
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
RXCUI
38574
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB02650
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY
MERCK INDEX
m11061
Created by admin on Fri Dec 15 16:34:03 UTC 2023 , Edited by admin on Fri Dec 15 16:34:03 UTC 2023
PRIMARY Merck Index