2-Chlorobenzylidene malononitrile (T3D4660)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-08 02:41:34 UTC
Update Date2014-12-24 20:26:54 UTC
Accession NumberT3D4660
Identification
Common Name2-Chlorobenzylidene malononitrile
ClassSmall Molecule
DescriptionThe compound 2-chlorobenzylidene malononitrile (also called o-chlorobenzylidene malononitrile) (chemical formula: C10H5ClN2), acyanocarbon, is the defining component of a tear gas commonly referred to as CS gas, which is used as a riot control agent. CS gas is an aerosol of avolatile solvent (a substance that dissolves other active substances and that easily evaporates) and 2-chlorobenzalmalononitrile, which is a solid compound at room temperature.
Compound Type
  • Aerosol Spray Component
  • Industrial/Workplace Toxin
  • Lachrymator
  • Nitrile
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC10H5ClN2
Average Molecular Mass188.613 g/mol
Monoisotopic Mass188.014 g/mol
CAS Registry Number2698-41-1
IUPAC Name2-[(2-chlorophenyl)methylidene]propanedinitrile
Traditional NameCS gas
SMILESClC1=CC=CC=C1C=C(C#N)C#N
InChI IdentifierInChI=1S/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H
InChI KeyInChIKey=JJNZXLAFIPKXIG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Oxidative phosphorylationNot Availablemap00190
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point93°C (199.4°F)
Boiling Point310°C (590°F)
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP2.59ALOGPS
logP2.78ChemAxon
logS-3.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.58 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.9 m³·mol⁻¹ChemAxon
Polarizability18.14 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1900000000-6abd80c426752e489d412021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f209ebee48221af6da722016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-5610586c26fa76dc21d82016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0900000000-60608b57fe21a4dffcec2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-6f7c3f1927f7a99411832016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-57a1cd42a19c702c44302016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-1900000000-629567af18fd9e1ff6472016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-660b5fed5bfa23df9ded2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-30e7cdd2bc4a55f85f5f2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-7592a6627619a15bb8cd2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-f8b7f713d0d93e47d0012021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-f8b7f713d0d93e47d0012021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ti-0900000000-8c33403761645269495f2021-10-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-3900000000-c5bb4d0352bed9583d092014-09-20View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityOrganic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (5)
MetabolismOrganic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health Effects2-Chlorobenzylidene malononitrile can cause severe pulmonary damage and damage of the heart and liver.
SymptomsSymptoms include eye irritation, tearing, burning sensation on the nose and throat, rhinorrhoea, excess salivation, constricting sensations in the chest, sneezing, coughing, and stinging or burning sensations in exposed skin.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID17604
ChEMBL IDCHEMBL1256101
ChemSpider ID16644
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCS_gas
References
Synthesis ReferenceNot Available
MSDST3D4660.pdf
General References
  1. Ballantyne B, Swanston DW. The comparative acute mammalian toxicity of 1-chloroacetophenone (CN) and 2-chlorobenzylidene malononitrile (CS). Arch Toxicol. 1978 Apr 27;40(2):75-95. [350197 ]
  2. Ballantyne, B., Gazzard, M. F., Swanston, D. W.: Irritancy testing by respiratory exposure. Ballantyne, B. Current Approaches in Toxicology (B. Ballantyne, ed.), p.129. Bristol: Wright and Sons 1977
  3. Lachrymation [Link]
  4. ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  5. Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. [Link]
  6. Wikipedia: CS gas [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]