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Record Information
Version4.0
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-09-27 08:27:36 UTC
HMDB IDHMDB0014575
Secondary Accession Numbers
  • HMDB14575
Metabolite Identification
Common NameLindane
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.
Structure
Thumb
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
(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
gamma-HexachlorocyclohexaneHMDB
Chemical FormulaC6H6Cl6
Average Molecular Weight290.83
Monoisotopic Molecular Weight287.860066434
IUPAC Name(1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-hexachlorocyclohexane
Traditional Nameβ-hexachlorobenzene
CAS Registry Number58-89-9
SMILES
Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl
InChI Identifier
InChI=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
DescriptionThis compound 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Parenteral:

  Enteral:

Role

Industrial application:

  Agriculture:

    Pesticide:

  Pharmaceutical industry:

    Antimicrobial agent:

Indirect biological role:

Physiological effect

Health effect:

  Observation:

  Health condition:

    Nervous system disorders:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point112.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0055 g/LNot Available
LogP3.8Not Available
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00o0-4930000000-75eb17ef01463cc739ebView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a80ad4b803c6cfbad7f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-94757a7ebf0ca8417382View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-4590000000-a1b5e62bd325a4408726View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-094eac0e1195e28c6f04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-b09c755105529e48aaa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0090000000-ee4766742eba17f9525eView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00105(0.00037-0.00179) uMAdult (>18 years old)BothNormal
    • Report on Human B...
details
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00431 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00431 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00431
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10481896
KEGG Compound IDC07075
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLindane
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID32888
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Strong M, Johnstone P: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. [PubMed:17636630 ]
  2. Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. [PubMed:18335087 ]
  3. 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. [PubMed:18138195 ]
  4. 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. [PubMed:16294879 ]
  5. 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. [PubMed:9763248 ]
  6. 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. [PubMed:9763247 ]
  7. 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. [PubMed:19287960 ]
  8. 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. [PubMed:10213519 ]
  9. 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. [PubMed:16727895 ]
  10. Katsumata K, Katsumata K: Norwegian scabies in an elderly patient who died after treatment with gammaBHC. Intern Med. 2003 Apr;42(4):367-9. [PubMed:12729329 ]
  11. 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. [PubMed:12801016 ]
  12. 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. [PubMed:10706031 ]
  13. 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. [PubMed:4908314 ]
  14. 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. [PubMed:20948097 ]

Enzymes

General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRB1
Uniprot ID:
P18505
Molecular weight:
54234.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Cole LM, Roush RT, Casida JE: Drosophila GABA-gated chloride channel: modified [3H]EBOB binding site associated with Ala-->Ser or Gly mutants of Rdl subunit. Life Sci. 1995;56(10):757-65. [PubMed:7885191 ]
  4. Sauviat MP, Pages N: [Cardiotoxicity of lindane, a gamma isomer of hexachlorocyclohexane]. J Soc Biol. 2002;196(4):339-48. [PubMed:12645305 ]
  5. Anand M, Agrawal AK, Rehmani BN, Gupta GS, Rana MD, Seth PK: Role of GABA receptor complex in low dose lindane (HCH) induced neurotoxicity: neurobehavioural, neurochemical and electrophysiological studies. Drug Chem Toxicol. 1998 Feb;21(1):35-46. [PubMed:9530529 ]
  6. Joy RM, Walby WF, Stark LG, Albertson TE: Lindane blocks GABAA-mediated inhibition and modulates pyramidal cell excitability in the rat hippocampal slice. Neurotoxicology. 1995 Summer;16(2):217-28. [PubMed:7566682 ]
  7. Bloomquist JR: Chloride channels as tools for developing selective insecticides. Arch Insect Biochem Physiol. 2003 Dec;54(4):145-56. [PubMed:14635176 ]
  8. Narahashi T: Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol. 1996 Jul;79(1):1-14. [PubMed:8841090 ]
  9. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
  10. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
  11. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]
General function:
Involved in ion transport
Specific function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:
GLRA1
Uniprot ID:
P23415
Molecular weight:
52623.4
References
  1. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
  2. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]
General function:
Involved in ion transport
Specific function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:
GLRA2
Uniprot ID:
P23416
Molecular weight:
52001.6
References
  1. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
  2. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]
General function:
Involved in ion transport
Specific function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:
GLRA3
Uniprot ID:
O75311
Molecular weight:
53799.8
References
  1. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
  2. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]
General function:
Involved in extracellular-glycine-gated chloride channel activity
Specific function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:
GLRB
Uniprot ID:
P48167
Molecular weight:
56121.6
References
  1. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
  2. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]