alpha-Hexachlorocyclohexane (CHEM000106)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (42)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:06 UTC
Update Date2026-04-05 10:22:10 UTC
Accession NumberCHEM000106
Identification
Common Namealpha-Hexachlorocyclohexane
ClassSmall Molecule
DescriptionHexachlorocyclohexane, Alpha- is one of eight isoforms of the commercially manufactured chemical hexachlorocyclohexane. It is used as an insecticide on fruit, vegetables, and forest crops and is also available as a prescription (lotion, cream, or shampoo) to treat head and body lice, and scabies. (2)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1alpha,2alpha,3beta,4beta,5alpha,6beta)-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
(1R,2C,3t,4t,5C,6t)-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
1alpha,2alpha,3beta,4alpha,5beta,6beta-HexachlorocyclohexaneChEBI
alpha-Benzene hexachlorideChEBI
alpha-BHCChEBI
alpha-HCHChEBI
alpha-HexachloraneChEBI
alpha-LindaneChEBI
(1a,2a,3b,4b,5a,6b)-1,2,3,4,5,6-HexachlorocyclohexaneGenerator
(1Α,2α,3β,4β,5α,6β)-1,2,3,4,5,6-hexachlorocyclohexaneGenerator
1a,2a,3b,4a,5b,6b-HexachlorocyclohexaneGenerator
1Α,2α,3β,4α,5β,6β-hexachlorocyclohexaneGenerator
a-Benzene hexachlorideGenerator
Α-benzene hexachlorideGenerator
a-BHCGenerator
Α-BHCGenerator
a-HCHGenerator
Α-HCHGenerator
a-HexachloraneGenerator
Α-hexachloraneGenerator
a-LindaneGenerator
Α-lindaneGenerator
a-HexachlorocyclohexaneGenerator
Α-hexachlorocyclohexaneGenerator
Chemical FormulaC6H6Cl6
Average Molecular Mass290.830 g/mol
Monoisotopic Mass287.860 g/mol
CAS Registry Number319-84-6
IUPAC Name(1R,2R,3R,4R,5S,6S)-1,2,3,4,5,6-hexachlorocyclohexane
Traditional Nameα-hexachlorocyclohexane
SMILESCl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H](Cl)[C@H]1Cl
InChI IdentifierInChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4-,5+,6+/m1/s1
InChI KeyJLYXXMFPNIAWKQ-SHFUYGGZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassCyclohexyl halides
Direct ParentCyclohexyl halides
Alternative Parents
Substituents
  • Cyclohexyl halide
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl chloride
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytosol
  • Membrane
  • Microsome
  • Mitochondrion
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Pyrimidine MetabolismSMP00046 map00240
Dna replicationNot Availablemap03030
ApoptosisNot Availablemap04210
Ddt DegradationNot AvailableNot Available
Abc transportersNot Availablemap02010
Cell cycleNot Availablemap04110
Arachidonic Acid MetabolismSMP00075 map00590
ApplicationsNot Available
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder or colorless vapor.
Experimental Properties
PropertyValue
Melting Point159.5°C
Boiling PointNot Available
Solubility0.002 mg/mL at 25 °C [WEIL,L et al. (1974)]
Predicted Properties
PropertyValueSource
Water Solubility0.0055 g/LALOGPS
logP3.94ALOGPS
logP4.35ChemAxon
logS-4.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.08 m³·mol⁻¹ChemAxon
Polarizability23.26 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a80ad4b803c6cfbad7f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-94757a7ebf0ca8417382Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-4590000000-a1b5e62bd325a4408726Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-094eac0e1195e28c6f04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-b09c755105529e48aaa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0090000000-ee4766742eba17f9525eSpectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
Mechanism of ToxicityHexachlorocyclohexane is a neurotoxin that interferes with GABA neurotransmitter function by interacting with the GABA-A receptor-chloride channel complex at the picrotoxin binding site, causing over stimulation of the central nervous system. It is also believed to inhibit sodium/potassium-transporting ATPases and to be an endocrine disruptor. In the liver, hexachlorocyclohexane is thought to cause oxidative stress by interfering with hepatic oxidative capacity and glutathione metabolism, increasing lipid metabolism, and inhibiting magnesium ATPase activity. Hexachlorocyclohexane may also inhibit gap junction and intercellular communication, leading to uncontrolled cell growth and tumor promotion. (2, 3, 1)
MetabolismHexachlorocyclohexane is absorbed through the skin, lungs, and intestines, then distributed mainly to the adipose tissue but also to the brain, kidney, muscle, and blood. Metabolism occurs via dechlorination, dehydrogenation, dehydrochlorination, and hydroxylation by hepatic cytochrome P-450 enzymes. The main metabolites are polychlorophenols and 1,2,4-trichlorocyclohexane-4,5-epoxide, which are excreted in the urine. (2)
Toxicity ValuesLD50: 177 mg/kg (Oral, Rat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesHexachlorocyclohexane is used as an insecticide on fruit, vegetables, and forest crops and is also available as a prescription (lotion, cream, or shampoo) to treat head and body lice, and scabies. (2)
Minimum Risk LevelChronic Oral: 0.008 mg/kg/day (4)
Health EffectsExposure to large amounts of hexachlorocyclohexane can harm the nervous system, producing a range of symptoms from headache and dizziness to seizures, convulsions and more rarely death. Hexachlorocyclohexane is known to damage the liver, kidneys, and immune system, as well as cause blood disorders and reproductive and developmental defects. Hexachlorocyclohexane is also potentially carcinogenic. (2, 3)
SymptomsExposure to large amounts of hexachlorocyclohexane can harm the nervous system, producing a range of symptoms from headache and dizziness to seizures, convulsions and more rarely death. (3)
TreatmentHexachlorocyclohexane poisoning is treated symptomatically. Gastric lavage, followed by the administration of activated charcoal, may be performed upon ingestion. (6)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlpha-Hexachlorocyclohexane
Chemspider IDNot Available
ChEBI ID39096
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available