Chlordane (CHEM000018)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (54)XML
Record Information
Version1.0
Creation Date2009-03-06 18:57:56 UTC
Update Date2026-03-26 20:32:15 UTC
Accession NumberCHEM000018
Identification
Common NameChlordane
ClassSmall Molecule
DescriptionChlordane is a manufactured chemical that was used as a pesticide in the United States from 1948 to 1988. Chlordane occurs in two isomers, called cis-chlordane (alpha-chlordane) and trans-chlordane (gamma-chlordane) (6).
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,4,5,6,7,10,10-Octachloro-4,7,8,9-tetrahydro-4,7-methyleneindaneChEBI
1,2,4,5,6,7,8,8-Octachloro-2,3,3a,4,7,7a-hexahydro-4,7-methanoindanChEBI
1,2,4,5,6,7,8,8-Octachloro-2,3,3a,4,7,7a-hexahydro-4,7-methanoindeneChEBI
1,3,4,7,8,9,10,10-Octachlorotricyclo[5.2.1.0(2,6)]dec-8-eneChEBI
ChlorindanChEBI
ChlordanMeSH
gamma-ChlordaneMeSH
gamma ChlordaneMeSH
Chemical FormulaC10H6Cl8
Average Molecular Mass409.779 g/mol
Monoisotopic Mass405.798 g/mol
CAS Registry Number57-74-9
IUPAC Name1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0^{2,6}]dec-8-ene
Traditional Name1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0^{2,6}]dec-8-ene
SMILESClC1CC2C(C1Cl)C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl
InChI IdentifierInChI=1S/C10H6Cl8/c11-3-1-2-4(5(3)12)9(16)7(14)6(13)8(2,15)10(9,17)18/h2-5H,1H2
InChI KeyBIWJNBZANLAXMG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassVinyl halides
Sub ClassVinyl chlorides
Direct ParentVinyl chlorides
Alternative Parents
Substituents
  • Chloroalkene
  • Haloalkene
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell junction
  • Cytoskeleton
  • Extracellular
  • Membrane
  • Membrane Fraction
  • Microsome
  • Mitochondrion
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Cell cycleNot Availablemap04110
Influenza aNot Availablemap05164
EicosanoidsNot AvailableNot Available
Degradation Of Aromatic CompoundsNot AvailableNot Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceColorless to amber liquid.
Experimental Properties
PropertyValue
Melting Point106°C
Boiling PointNot Available
Solubility5.6e-05 mg/mL at 25 °C [SANBORN,JR et al. (1976)]
Predicted Properties
PropertyValueSource
Water Solubility6.9e-05 g/LALOGPS
logP6.02ALOGPS
logP5.27ChemAxon
logS-6.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.38 m³·mol⁻¹ChemAxon
Polarizability32.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0001900000-cbe0d008d48efeebddc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0004900000-b9d20b4f44fa679d7984Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2119000000-8e3e670086348c43ae15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-11a7620b8bbb40ee8c05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0009400000-73bfd1e73d846959f213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-1009000000-3ce6dcfd1ccf213fc417Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-fec6314a59e20dc9ec83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-fec6314a59e20dc9ec83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0014900000-13ab4e789b1a9bb5747bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-59f02e9eabb99ef7ea2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-59f02e9eabb99ef7ea2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0000900000-59f02e9eabb99ef7ea2aSpectrum
MSMass Spectrum (Electron Ionization)splash10-00fr-3698000000-2654b4a8beefe64bb070Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (11) ; inhalation (5)
Mechanism of ToxicityChlordane is believed to bind irreversibly to DNA, leading to cell death or altered cellular function. It also affects transcription by antagonizing estrogen-related receptors. Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. Chlordane has also been shown to bind and activate retinoic acid receptor, causing various developmental defects, and inhibit alkaline phosphatases in hepatic and renal tissues. (7, 1, 2, 3, 4)
MetabolismChlordane is highly lipophilic and is thus easily absorbed by ingestion, inhalation, and dermal exposure, then stored mainly in the fat. Chlordane is metabolized mainly in the liver and kidney. Metabolism is slow, and is believed to occur by multiple pathways involving cytochrome P-450 enzymes, glutathione-S-transferase type enzymes, and microsomal mixed-function oxidase systems. The metabolites are generally less toxic and include chlordene chlorohydrin, monohydroxylated dihydrochlordene, and oxychlordane. They are excreted in the urine and faeces. (7)
Toxicity ValuesLD50: 200 mg/kg (Oral, Rat) (12) LD50: 343 mg/kg (Intraperitoneal, Rat) (12) LD50: 10 mg/kg (Intravenous, Mouse) (13) LD50: 780 mg/kg (Dermal, Rat) (13) LC50: 100 mg/m3 over 4 hours (Inhalation, Cat) (13)
Lethal Dose100 mg/kg for an adult human. (14)
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (9)
Uses/SourcesChlordane was used as a pesticide. (6)
Minimum Risk LevelIntermediate Inhalation: 0.0002 mg/m3 (8) Chronic Inhalation: 0.00002 mg/m3 (8) Acute Oral: 0.001 mg/kg/day (8) Intermediate Oral: 0.0006 mg/kg/day (8) Chronic Oral: 0.0006 mg/kg/day (8)
Health EffectsChlordane is a central nervous system stimulant, and can also damage the digestive system and the liver. Large doses have been known to cause convulsions, respiratory failure, and death. Chlordane is also known to have adverse reproductive and developmental effects. (7)
SymptomsIngestion and inhalation of chlordane cause headaches, irritability, confusion, weakness, vision problems, vomiting, stomach cramps, diarrhea, and jaundice. (7)
TreatmentTreatment is symptomatic. It is aimed at controlling convulsions, coma, and respiratory depression. Gastric lavage, followed by the administration of activated charcoal, may be performed following ingestion. (10)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0250287
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChlordane
Chemspider ID5772
ChEBI ID34623
PubChem Compound IDNot Available
Kegg Compound IDC14176
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available