Page last updated: 2024-09-22

o-chlorobenzylidenemalonitrile

Description

o-Chlorobenzylidenemalonitrile: A riot control agent which causes temporary irritation of the eyes and the mucosal surface of the respiratory tract. It is a more potent irritant than OMEGA-CHLOROACETOPHENONE, but less incapacitating. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID17604
CHEMBL ID1256101
CHEBI ID188626
SCHEMBL ID436060
MeSH IDM0015157

Synonyms (84)

Synonym
nsc637336
nsc-637336
2-(2-chlorobenzylidene)malononitrile
2-[(2-chlorophenyl)methylene]propanedinitrile
o-chlorobenzalmalonitrile
alonitrile
hsdb 4346
tl 238
einecs 220-278-9
cs (lacrimator)
propanedinitrile, ((2-chlorophenyl)methylene)-
o-chlorobenzylidenemalononitrile
malononitrile, o-chlorobenzylidene-
ortho-chlorobenzylidene malononitrile
chlorobenzylidenemalononitrile
o-chlorobenzylidene malononitrile
2-chlorobenzylidene malonitrile
2-chlorobenzylidene malononitrile
brn 1866635
ccris 2377
((2-chloro-phenyl)methylene)propanenitrile
((2-chlorophenyl)methylene)malononitrile
propanedinitrile, ((2-chlorophenyl)methylene)
nsc 542
o-chlorobenzylidenemalonitrile
beta,beta-dicyano-o-chlorostyrene
(o-chlorobenzylidene)malonitrile
2-chlorobenzalmalononitrile
nci-c55118
(2-chlorobenzylidene)malononitrile
2698-41-1
malononitrile, (o-chlorobenzylidene)-
(o-chlorobenzal)malononitrile
(o-chlorobenzylidene)malononitrile
2-chlorobmn
2-chlorobenzylidenemalononitrile
propanedinitrile, [(2-chlorophenyl)methylene]-
propanedinitrile, [(2-chlorophenyl)methylene]
usaf kf-11
nsc-542
o-chlorobenzylidenemalonic nitrile
nsc542
wln: ncycn&u1r bg
.beta.,.beta.-dicyano-o-chlorostyrene
o-chlorobenzalmalononitrile
AKOS000504237
2-[(2-chlorophenyl)methylidene]propanedinitrile
CHEBI:188626
A18547
[(2-chlorophenyl)methylene]malononitrile
d8317iav7q ,
unii-d8317iav7q
propanedinitrile, 2-((2-chlorophenyl)methylene)-
bdbm50327657
CHEMBL1256101 ,
FT-0610792
AM84860
2-chlorobenzalmalononitrile [hsdb]
chlorobenzalmalonitrile, o-
o-chlorobenzylidenemalononitrile [mi]
2-((2-chlorophenyl)methylene)propanedinitrile
chlorobenzylidene malononitrile
gtpl4158
cs gas (lacrimator)
SCHEMBL436060
(2-chlorobenzylidene)propanedinitrile
2-chloro bmn
2-chlorobenzylidenemaloninitrile
propanedinitrile, 2-[(2-chlorophenyl)methylene]-
beta,bbeta-dicyano-o-chlorostyrene
2-(2-chlorobenzylidene)malononitrile #
W-107137
DTXSID9020297
propanedinitrile, [(chlorophenyl)methylene]-
2-[(2-chlorophenyl)methylene]malononitrile
Q209357
2-((2-chlorophenyl)methylene)malononitrile
AS-11303
STL196772
H11803
[(2-chlorophenyl)methylene]malononitrile; ((2-chlorophenyl)methylene)propanedinitrile
mfcd00019784
SY106828
CS-0095253

Drug Classes (1)

ClassDescription
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
[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 (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transient receptor potential cation channel subfamily A member 1Homo sapiens (human)EC50 (µMol)0.00090.00033.166210.0000AID516893
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
monoatomic ion transportTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
intracellular calcium ion homeostasisTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
cell surface receptor signaling pathwayTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to coldTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to xenobiotic stimulusTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to organic substanceTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to organic cyclic compoundTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
sensory perception of painTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
calcium-mediated signalingTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
response to painTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
thermoceptionTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
protein homotetramerizationTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
cellular response to hydrogen peroxideTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
calcium ion transmembrane transportTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
cellular response to organic substanceTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
calcium channel activityTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
channel activityTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
intracellularly gated calcium channel activityTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
identical protein bindingTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
temperature-gated cation channel activityTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
stereocilium bundleTransient receptor potential cation channel subfamily A member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID1346556Human TRPA1 (Transient Receptor Potential channels)2008Toxicology and applied pharmacology, Sep-01, Volume: 231, Issue:2
Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor.
AID516895Agonist activity at human TRPA1 expressed in T-REx-HEK293 cells assessed as concentration required to incapacitate 50% of the population exposed to tear gas2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Analogues of morphanthridine and the tear gas dibenz[b,f][1,4]oxazepine (CR) as extremely potent activators of the human transient receptor potential ankyrin 1 (TRPA1) channel.
AID516894Agonist activity at human TRPA1 expressed in T-REx-HEK293 cells assessed as threshold concentration after 1 min2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Analogues of morphanthridine and the tear gas dibenz[b,f][1,4]oxazepine (CR) as extremely potent activators of the human transient receptor potential ankyrin 1 (TRPA1) channel.
AID516893Agonist activity at human TRPA1 expressed in T-REx-HEK293 cells assessed as increase of intracellular calcium level by FDSS assay2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Analogues of morphanthridine and the tear gas dibenz[b,f][1,4]oxazepine (CR) as extremely potent activators of the human transient receptor potential ankyrin 1 (TRPA1) channel.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (134)

TimeframeStudies, This Drug (%)All Drugs %
pre-199041 (30.60)18.7374
1990's37 (27.61)18.2507
2000's33 (24.63)29.6817
2010's20 (14.93)24.3611
2020's3 (2.24)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.71%)5.53%
Reviews10 (7.14%)6.00%
Case Studies30 (21.43%)4.05%
Observational1 (0.71%)0.25%
Other98 (70.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (5)

ArticleYear
Towards Development of a Dermal Pain Model: In Vitro Activation of Rat and Human Transient Receptor Potential Ankyrin Repeat 1 and Safe Dermal Injection of o-Chlorobenzylidene Malononitrile to Rat.
Basic & clinical pharmacology & toxicology, Volume: 117, Issue: 6
2015
A repeated dose study of the toxicity of inhaled 2-chlorobenzylidene malononitrile (CS) aerosol in three species of laboratory animal.
Archives of toxicology, Volume: 52, Issue: 3
1983
Acute toxicity and primary irritancy of 2-amino-3,5-dicyano-4-o-chlorophenyl-6-ethoxypyridine.
Drug and chemical toxicology, Volume: 8, Issue: 3
1985
Mutagenicity and cytotoxicity of 2-chlorobenzylidene malonitrile (CS) and metabolites in V79 Chinese hamster cells.
Archives of toxicology, Volume: 63, Issue: 4
1989
The comparative acute mammalian toxicity of 1-chloroacetophenone (CN) and 2-chlorobenzylidene malononitrile (CS).
Archives of toxicology, Apr-27, Volume: 40, Issue: 2
1978
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (3)

ArticleYear
2-Chlorobenzylmercapturic acid, a metabolite of the riot control agent 2-chlorobenzylidene malononitrile (CS) in the rat.
Archives of toxicology, Volume: 54, Issue: 2
1983
A repeated dose study of the toxicity of inhaled 2-chlorobenzylidene malononitrile (CS) aerosol in three species of laboratory animal.
Archives of toxicology, Volume: 52, Issue: 3
1983
The acute mammalian toxicology of dibenz(b,f)-1,4-oxazepine.
Toxicology, Volume: 8, Issue: 3
1977
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]