gamma-Hexachlorocyclohexane (CHEM000028)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (53)XML
Record Information
Version1.0
Creation Date2009-03-06 18:57:57 UTC
Update Date2026-05-14 16:38:33 UTC
Accession NumberCHEM000028
Identification
Common Namegamma-Hexachlorocyclohexane
ClassSmall Molecule
DescriptionAn organochlorine insecticide that has been used as a pediculicide and a scabicide. Lindane has been banned in California, United Kingdom, Australia, and many western countries due to concerns about neurotoxicity and adverse effects on the environment. In Canada, Lindane is not recommmended as a first-line therapy due to reports of resistance, neurotoxicity, and bone marrow suppression, but has been approved by the FDA as a second-line therapy for topical treatment of pediculosis capitis (head lice), pediculosis pubis (pubic lice), or scabies in patients greater than two years of age who cannot tolerate or have failed first-line treatment.
Contaminant Sources
  • Clean Air Act Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antiscabies Agent
  • Drug
  • Insecticide
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1alpha,2alpha,3beta,4alpha,5alpha,6beta)-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
(1R,2C,3t,4C,5C,6t)-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
1,2,3,4,5,6-HexachlorocyclohexaneChEBI
Benzene hexachlorideChEBI
gamma-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
gamma-Benzene hexachlorideChEBI
gamma-BHCChEBI
gamma-HCHChEBI
gamma-HexachlorzyklohexanChEBI
gamma-LindaneChEBI
KwellChEBI
LindanChEBI
gamma-HexachlorocyclohexaneKegg
(1a,2a,3b,4a,5a,6b)-1,2,3,4,5,6-HexachlorocyclohexaneGenerator
(1Α,2α,3β,4α,5α,6β)-1,2,3,4,5,6-hexachlorocyclohexaneGenerator
g-1,2,3,4,5,6-HexachlorocyclohexaneGenerator
Γ-1,2,3,4,5,6-hexachlorocyclohexaneGenerator
g-Benzene hexachlorideGenerator
Γ-benzene hexachlorideGenerator
g-BHCGenerator
Γ-BHCGenerator
g-HCHGenerator
Γ-HCHGenerator
g-HexachlorzyklohexanGenerator
Γ-hexachlorzyklohexanGenerator
g-LindaneGenerator
Γ-lindaneGenerator
g-HexachlorocyclohexaneGenerator
Γ-hexachlorocyclohexaneGenerator
LindaneChEBI
Chemical FormulaC6H6Cl6
Average Molecular Mass290.830 g/mol
Monoisotopic Mass287.860 g/mol
CAS Registry Number58-89-9
IUPAC Name(1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-hexachlorocyclohexane
Traditional Nameβ-hexachlorobenzene
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+
InChI KeyJLYXXMFPNIAWKQ-GNIYUCBRSA-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
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder or colorless vapor.
Experimental Properties
PropertyValue
Melting Point112.5°C
Boiling Point323.4°C
Solubility7.3 mg/L (at 25°C)
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
Polarizability23.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00o0-4930000000-75eb17ef01463cc739ebSpectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00o0-4930000000-75eb17ef01463cc739ebSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-5890000000-755b89193e302e983a48Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-93872df9a57f35cad313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-93872df9a57f35cad313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2090000000-ed4e600a7049c9ec17efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-dd9d13ed654b099f3e28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-a62c38d355f5e13a1765Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-dd9d13ed654b099f3e28Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4) Lindane is absorbed significantly through the skin. A mean peak blood concentration of 28 nanograms per mL occurred in infants and children 6 hours after total body application of lindane lotion for scabies.
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 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. (4, 5, 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. (4). Other metabolites include 2-chlorophenol, 0-chlorophenol, chlorocyclohexane, chlorocyclohexanol. Half Life: 18 hours
Toxicity ValuesLindane is a moderately toxic compound via oral exposure, with a reported oral LD50 of 88 to 190 mg/kg in rats. It is moderately toxic via the dermal route as well, with reported dermal LD50 values of 500 to 1000 mg/kg in rats, 300 mg/kg in mice, 400 mg/kg in guinea pigs, and 300 mg/kg in rabbits. LD50: 76 mg/kg (Oral, Rat) (10) LD50: 50 mg/kg (Dermal, Rabbit) (10) LD50: 125 mg/kg (Intraperitoneal, Mouse) (10)
Lethal Dose28 g for an adult human. (8)
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (7)
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. (4) Hexachlorocyclohexane is also used or the treatment of patients infested with Sarcoptes scabiei or pediculosis capitis who have either failed to respond to adequate doses, or are intolerant of other approved therapies.
Minimum Risk LevelAcute Oral: 0.003 mg/kg/day (6) Intermediate Oral: 0.00001 mg/kg/day (6)
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. (4, 5)
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. (5)
TreatmentHexachlorocyclohexane poisoning is treated symptomatically. Gastric lavage, followed by the administration of activated charcoal, may be performed upon ingestion. (9)
Concentrations
Not Available
DrugBank IDDB00431
HMDB IDHMDB0014575
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLindane
Chemspider ID10481896
ChEBI ID32888
PubChem Compound IDNot Available
Kegg Compound IDC07075
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sharma HR, Kaushik A, Kaushik CP: Pesticide residues in bovine milk from a predominantly agricultural state of Haryana, India. Environ Monit Assess. 2007 Jun;129(1-3):349-57. doi: 10.1007/s10661-006-9368-5. Epub 2006 Dec 16.
2. Strong M, Johnstone P: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320.
3. Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128.
4. REES BE, RALEY TG, DAVIS ED: Prehatiching treatment of irrigated lands with DDT, dichlorodiphenyl dichloroethane, and gammabenzene hexachloride for control of flood water mosquitoes. J Econ Entomol. 1949 Aug;42(4):586-90.
5. Lundstedt-Enkel K, Tysklind M, Trygg J, Schuller P, Asplund L, Eriksson U, Haggberg L, Odsjo T, Hjelmberg M, Olsson M, Orberg J: A statistical resampling method to calculate biomagnification factors exemplified with organochlorine data from herring (Clupea harengus) muscle and guillemot (Uria aalge) egg from the Baltic sea. Environ Sci Technol. 2005 Nov 1;39(21):8395-402.
6. Alm H, Torner H, Tiemann U, Kanitz W: Influence of organochlorine pesticides on maturation and postfertilization development of bovine oocytes in vitro. Reprod Toxicol. 1998 Sep-Oct;12(5):559-63.
7. Tiemann U, Pohland R, Kuchenmeister U, Viergutz T: Influence of organochlorine pesticides on transmembrane potential, oxidative activity, and ATP-induced calcium release in cultured bovine oviductal cells. Reprod Toxicol. 1998 Sep-Oct;12(5):551-7.
8. Belpomme D, Irigaray P, Ossondo M, Vacque D, Martin M: Prostate cancer as an environmental disease: an ecological study in the French Caribbean islands, Martinique and Guadeloupe. Int J Oncol. 2009 Apr;34(4):1037-44.
9. Tiemann U, Pohland R: Inhibitory effects of organochlorine pesticides on intercellular transfer of Lucifer Yellow in cultured bovine oviductal cells. Reprod Toxicol. 1999 Mar-Apr;13(2):123-30.
10. Tiemann U, Pohland R, Schneider F: Influence of organochlorine pesticides on physiological potency of cultured granulosa cells from bovine preovulatory follicles. Theriogenology. 1996 Jul 15;46(2):253-65.
11. Katsumata K, Katsumata K: Norwegian scabies in an elderly patient who died after treatment with gammaBHC. Intern Med. 2003 Apr;42(4):367-9.
12. Storelli MM, Stuffler RG, Marcotrigianoi GO: Polycyclic aromatic hydrocarbons, polychlorinated biphenyls, chlorinated pesticides (DDTs), hexachlorocyclohexane, and hexachlorobenzene residues in smoked seafood. J Food Prot. 2003 Jun;66(6):1095-9.
13. Corrigan FM, Wienburg CL, Shore RF, Daniel SE, Mann D: Organochlorine insecticides in substantia nigra in Parkinson's disease. J Toxicol Environ Health A. 2000 Feb 25;59(4):229-34.
14. Luczak J, Sitkiewicz D: [Effect of Tritox (DDT, DMDT, gammaHCH) on physico-chemical properties and indices of microbial pollution of water]. Rocz Panstw Zakl Hig. 1969;20(4):495-501.
15. Panvelkar V, Chari KV: Gammabenzene hexachloride-induced convulsions in an HIV positive individual. Indian J Dermatol Venereol Leprol. 1996 Sep-Oct;62(5):306-7.