Compounds > chloroacetonitrile
Page last updated: 2024-12-05

chloroacetonitrile

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID7856
CHEMBL ID3187297
CHEBI ID82416
MeSH IDM0189128

Synonyms (64)

Synonym
2-chloro-acetonitrile
monochloroacetonitrile
.alpha.-chloroacetonitrile
wln: nc1g
chloracetonitrile
usaf kf-5
chloromethyl cyanide
monochloromethyl cyanide
acetonitrile, chloro-
nsc6180
chloroethanenitrile
2-chloroacetonitrile
chloroacetonitrile
nsc-6180
107-14-2
acetic acid,chloro,nitrile
inchi=1/c2h2cln/c3-1-2-4/h1h
hsdb 6317
alpha-chloroacetonitrile
un2668
brn 0506028
nsc 6180
ai3-52205
einecs 203-467-0
ccris 2670
chloroacetonitrile, 99%
AKOS000118818
NCGC00248886-01
cn524k9dxd ,
acetonitrile, 2-chloro-
4-02-00-00492 (beilstein handbook reference)
unii-cn524k9dxd
chloroacetonitrile [un2668] [poison]
chloro-acetonitrile
C19360
dtxsid7021524 ,
tox21_200957
cas-107-14-2
dtxcid301524
NCGC00258510-01
FT-0623631
chloroacetonitrile [iarc]
chloroacetonitrile [hsdb]
CHEBI:82416 ,
c2h2cln
chloro acetonitrile
clch2cn
cyanomethyl chloride
2chloroacetonitrile
chloroactonitrile
chloroaceto nitrile
2-cloroacetonitrile
un 2668
ch2clcn
CHEMBL3187297
mfcd00001885
J-509002
F2190-0287
chloroacetonitrile, purum, >=99.0% (gc)
Q2196683
BCP27602
STL185582
chloroethane nitrile
EN300-19495

Research Excerpts

Overview

Chloroacetonitrile (CAN) is a disinfection by-product of chlorination of drinking water. It is considered as a direct-acting mutagenic and carcinogenic agent.

ExcerptReferenceRelevance
"Chloroacetonitrile (CAN) is a halogenated acetonitrile often produced while disinfecting drinking water. "( Chloroacetonitrile exposure induces endoplasmic reticulum stress and affects spindle assembly in mouse oocytes.
Chen, YZ; Liu, Y; Liu, YC; Qi, ZQ; Qiao, FX; Sun, MX; Wang, HL; Xu, CL; Xu, ZR, 2023)		3.8
"Chloroacetonitrile (CAN) is a by-product of chlorination of drinking water. "( Chloroacetonitrile induces intrauterine growth restriction and musculoskeletal toxicity in fetal mouse.
Abdel-Naim, AB; Ahmed, AE; El-Mazar, HM; Nagy, AA, 2008)		3.23
"Chloroacetonitrile (CAN) is a disinfection by-product of chlorination of drinking water. "( Chloroacetonitrile induces oxidative stress and apoptosis in mouse fetal liver.
Abdel-Naim, AB; Ahmed, AE; El-Mazar, HM; Mohamadin, AM; Nagy, AA, 2009)		3.24
"Chloroacetonitrile is a disinfectant by-product of chlorination of drinking water and is considered as a direct-acting mutagenic and carcinogenic agent. "( Mechanisms of hepatotoxicity of chloroacetonitrile - an end product of water chlorination.
Abo-Salem, OM; Al-Zahrani, SS; Ghonaim, MM, 2013)		2.12
"Chloroacetonitrile (CAN) is a disinfection by-product of chlorination of drinking water. "( Myeloperoxidase-catalyzed oxidation of chloroacetonitrile to cyanide.
Abdel-Naim, AB; Mohamadin, AM, 2004)		2.04
"Chloroacetonitrile (CAN), is a disinfectant by-product of chlorination of drinking water. "( Chloroacetonitrile-induced toxicity and oxidative stress in rat gastric epithelial cells.
Abdel-Naim, AB; Mohamadin, AM, 1999)		3.19

Toxicity

ExcerptReferenceRelevance
" These toxic responses to CAN were dependent on both concentration and duration of exposure to CAN."( Chloroacetonitrile-induced toxicity and oxidative stress in rat gastric epithelial cells.
Abdel-Naim, AB; Mohamadin, AM, 1999)		1.75
" The present study was designed to investigate the potential adverse effects of intrauterine exposure to CAN on fetal body weight and development of the musculoskeletal system in mice."( Chloroacetonitrile induces intrauterine growth restriction and musculoskeletal toxicity in fetal mouse.
Abdel-Naim, AB; Ahmed, AE; El-Mazar, HM; Nagy, AA, 2008)		1.79
"The concept of multiple modes of toxic action denotes that an individual chemical can induce two or more toxic effects within the same series of concentrations, for example, reactive toxicity and narcosis."( Mixture toxicity of SN2-reactive soft electrophiles: 1. Evaluation of mixtures containing α-halogenated acetonitriles.
Dawson, DA; Jeyaratnam, J; Mooneyham, T; Pöch, G; Schultz, TW, 2010)		0.36
" It is possible that HAN disruption of the normal cell cycle and the generation of aberrant cells with an abnormal number of chromosomes may contribute to cancer induction and perhaps be involved in the induction of adverse pregnancy outcomes associated with long-term consumption of disinfected water."( Toxicity of drinking water disinfection byproducts: cell cycle alterations induced by the monohaloacetonitriles.
Komaki, Y; Mariñas, BJ; Plewa, MJ, 2014)		0.4

Dosage Studied

ExcerptRelevanceReference
" Based on an initial dose-response experiment, CAN (25mg/(kgday)) was given orally to pregnant mice at gestation day (GD) 6, till GD 18."( Chloroacetonitrile induces oxidative stress and apoptosis in mouse fetal liver.
Abdel-Naim, AB; Ahmed, AE; El-Mazar, HM; Mohamadin, AM; Nagy, AA, 2009)		1.8
" Time-course and dose-response studies were performed to examine the mechanism of chloroacetonitrile-induced hepatotoxicity."( Mechanisms of hepatotoxicity of chloroacetonitrile - an end product of water chlorination.
Abo-Salem, OM; Al-Zahrani, SS; Ghonaim, MM, 2013)		0.9
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
nitrileA compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency12.70750.000221.22318,912.5098AID1259243
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency56.76210.001022.650876.6163AID1224838
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency52.76670.003041.611522,387.1992AID1159552; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency56.76210.001530.607315,848.9004AID1224841; AID1224842; AID1224848; AID1224849
estrogen nuclear receptor alphaHomo sapiens (human)Potency33.37040.000229.305416,493.5996AID1259244; AID743075; AID743079
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency71.45930.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency71.45930.001551.739315,848.9004AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (23.81)18.2507
2000's9 (42.86)29.6817
2010's6 (28.57)24.3611
2020's1 (4.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.98

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.98 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index53.08 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.98)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloroacetaldehyde
[no description available]		7.0810organochlorine compound
acetaldehyde
Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.		7.0810aldehydecarcinogenic agent;
EC 3.5.1.4 (amidase) inhibitor;
electron acceptor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
mutagen;
oxidising agent;
Saccharomyces cerevisiae metabolite;
teratogenic agent
toluene
methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.		2.0210methylbenzene;
toluenes;
volatile organic compound		cholinergic antagonist;
fuel additive;
neurotoxin;
non-polar solvent
chloral hydrate
[no description available]		2.0710aldehyde hydrate;
ethanediol;
organochlorine compound		general anaesthetic;
mouse metabolite;
sedative;
xenobiotic
potassium chloride
Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.		2.0210inorganic chloride;
inorganic potassium salt;
potassium salt		fertilizer
cyanides
Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.		2.0210pseudohalide anionEC 1.9.3.1 (cytochrome c oxidase) inhibitor
dimethylformamide
Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.		2.0210formamides;
volatile organic compound		geroprotector;
hepatotoxic agent;
polar aprotic solvent
acetonitrile
acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.		2.5320aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		2.7430dialdehydebiomarker
trichloroacetonitrile
[no description available]		2.4520aliphatic nitrile;
organochlorine compound
2,2-dichloroacetamide
[no description available]		2.0810
dichloroacetonitrile
dichloroacetonitrile: by-product of water chlorination; structure given in first source		2.4520aliphatic nitrile
dibromoacetonitrile
dibromoacetonitrile: by-product of water chlorination; structure given in first source		2.7530aliphatic nitrile
osmium
Osmium: A very hard, gray, toxic, and nearly infusible metal element, atomic number 76, atomic weight 190.2, symbol Os.		2.0410iron group element atom;
platinum group metal atom
ruthenium
Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.		2.0410iron group element atom;
platinum group metal atom
chloramine
[no description available]		7.0810halide
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		2.0210cobalt group element atom;
metal allergen		micronutrient
bilirubin
[no description available]		2.0810biladienes;
dicarboxylic acid		antioxidant;
human metabolite;
mouse metabolite
4-hydroxy-2-nonenal
4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.		2.02104-hydroxynon-2-enal;
4-hydroxynonenal
mocetinostat
mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).		2.0210aminopyrimidine;
benzamides;
pyridines;
secondary amino compound;
secondary carboxamide;
substituted aniline		antineoplastic agent;
apoptosis inducer;
autophagy inducer;
cardioprotective agent;
EC 3.5.1.98 (histone deacetylase) inhibitor;
hepatotoxic agent
cobinamide
[no description available]		7.0210
vitamin b 12
Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.		2.0210
deoxyguanosine
[no description available]		2.9440purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
guanine
[no description available]		7102-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
8-hydroxy-2'-deoxyguanosine
8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.		2.7130guanosinesbiomarker
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Liver
[description not available]		02.1710
Liver Neoplasms
Tumors or cancer of the LIVER.		02.1710
Body Weight, Fetal
[description not available]		02.0410
Fetal Growth Restriction
[description not available]		02.0410
Fetal Resorption
The disintegration and assimilation of the dead FETUS in the UTERUS at any stage after the completion of organogenesis which, in humans, is after the 9th week of GESTATION. It does not include embryo resorption (see EMBRYO LOSS).		02.0410
Abnormalities, Musculoskeletal
[description not available]		02.0410
Abnormalities, Drug-Induced
Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.		02.0410
Fetal Growth Retardation
Failure of a FETUS to attain expected GROWTH.		02.0410
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		07.9540
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.0510
Acute Liver Injury, Drug-Induced
[description not available]		02.0810
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.0810
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0210
Nerve Degeneration
Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.		02.4320
Abnormalities, Congenital, Nervous System
[description not available]		02.0210
Delayed Effects, Prenatal Exposure
[description not available]		02.0210
Encephalopathy, Toxic
[description not available]		02.0210
Experimental Neoplasms
[description not available]		0210