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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

Molecular Formula C2HCl3O
Molecular Weight 147.388
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Simultaneous detection of trichloroethylene alcohol and acetate in rat urine by gas chromatography-mass spectrometry.
2003 Jun 15
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
Some drinking-water disinfectants and contaminants, including arsenic.
2004
"Receptive substances": John Newport Langley (1852-1925) and his path to a receptor theory of drug action.
2004 Apr
Aldehyde dehydrogenase, nitric oxide synthase and superoxide in ex vivo nitrate tolerance in rat aorta.
2004 Aug 2
The effect of fasting practice on sedation with chloral hydrate.
2004 Dec
Photolysis of chloral under atmospheric conditions.
2004 Feb 1
Environmental contaminant and disinfection by-product trichloroacetaldehyde stimulates T cells in vitro.
2004 Jan
Tricyclic furanoid dichloroacetyl orthoesters of D-mannose from 1,2-O-trichloroethylidene-beta-D-mannofuranose.
2004 Jul 12
Rate constants for hydrogen abstraction from alkoxides by a perfluoroalkyl radical. An oxyanion accelerated process.
2004 Jul 21
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
The history of barbiturates a century after their clinical introduction.
2005 Dec
Pharmacodynamics of chloral hydrate in former preterm infants.
2005 Jul
Self-assembled structure of nanoparticles at a liquid-liquid interface.
2005 Mar 29
The role of serendipity in drug discovery.
2006
Occurrence of a new generation of disinfection byproducts.
2006 Dec 1
Exposure to a metabolite of the environmental toxicant, trichloroethylene, attenuates CD4+ T cell activation-induced cell death by metalloproteinase-dependent FasL shedding.
2006 Jul
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
Issues in the pharmacokinetics of trichloroethylene and its metabolites.
2006 Sep
Key scientific issues in the health risk assessment of trichloroethylene.
2006 Sep
On cannabis, chloral hydrate, and career cycles of psychotropic drugs in medicine.
2006 Spring
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
Sleep disorders in children.
2007 Sep 1
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
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
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
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:34:03 GMT 2023
Edited
by admin
on Fri Dec 15 16:34:03 GMT 2023
Record UNII
FLI06WS32H
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
Code System Code Type Description
PUBCHEM
6407
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
DAILYMED
FLI06WS32H
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
MESH
C021100
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-911-5
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
HSDB
2557
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
CHEBI
48814
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
WIKIPEDIA
CHLORAL
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
NCI_THESAURUS
C76937
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
FDA UNII
FLI06WS32H
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
CAS
75-87-6
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID7024744
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
RXCUI
38574
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB02650
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY
MERCK INDEX
m11061
Created by admin on Fri Dec 15 16:34:03 GMT 2023 , Edited by admin on Fri Dec 15 16:34:03 GMT 2023
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY