Lindane

Basic Info

Common NameLindane(F03292)
2D Structure
Description

Technical grade hexachlorocyclohexane is a manufactured chemical that typically consists of the alpha, beta, delta, epsilon, and gamma isomers of 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. (L108)

FRCD IDF03292
CAS Number608-73-1
PubChem CID727
FormulaC6H6Cl6
IUPAC Name

1,2,3,4,5,6-hexachlorocyclohexane

InChI Key

JLYXXMFPNIAWKQ-UHFFFAOYSA-N

InChI

InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H

Canonical SMILES

C1(C(C(C(C(C1Cl)Cl)Cl)Cl)Cl)Cl

Isomeric SMILES

C1(C(C(C(C(C1Cl)Cl)Cl)Cl)Cl)Cl

WikipediaLindane
Synonyms
        
            lindane
        
            beta-HCH
        
            gamma-HCH
        
            gamma-BHC
        
            alpha-HCH
        
            Kwell
        
            Benzene hexachloride
        
            Hexicide
        
            Hexachlorane
        
            gamma-hexachlorocyclohexane
Classifies
                

                  
                    Illegal Additives
                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganohalogen compounds
ClassAlkyl halides
SubclassCyclohexyl halides
Intermediate Tree NodesNot available
Direct ParentCyclohexyl halides
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
SubstituentsCyclohexyl halide - Hydrocarbon derivative - Organochloride - Alkyl chloride - Aliphatic homomonocyclic compound
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.

Properties

Property NameProperty Value
Molecular Weight290.814
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Complexity104
Monoisotopic Mass287.86
Exact Mass289.857
XLogP3.8
Formal Charge0
Heavy Atom Count12
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9862
Human Intestinal AbsorptionHIA+0.9918
Caco-2 PermeabilityCaco2+0.8369
P-glycoprotein SubstrateNon-substrate0.8826
P-glycoprotein InhibitorNon-inhibitor0.9733
Non-inhibitor0.9944
Renal Organic Cation TransporterNon-inhibitor0.8593
Distribution
Subcellular localizationMitochondria0.6373
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8522
CYP450 2D6 SubstrateNon-substrate0.7758
CYP450 3A4 SubstrateNon-substrate0.7335
CYP450 1A2 InhibitorInhibitor0.6037
CYP450 2C9 InhibitorNon-inhibitor0.7892
CYP450 2D6 InhibitorNon-inhibitor0.9592
CYP450 2C19 InhibitorNon-inhibitor0.5936
CYP450 3A4 InhibitorNon-inhibitor0.9007
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7408
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9077
Non-inhibitor0.9617
AMES ToxicityNon AMES toxic0.9754
CarcinogensCarcinogens 0.5058
Fish ToxicityHigh FHMT0.8438
Tetrahymena Pyriformis ToxicityHigh TPT0.9694
Honey Bee ToxicityHigh HBT0.8108
BiodegradationNot ready biodegradable0.9271
Acute Oral ToxicityIII0.8388
Carcinogenicity (Three-class)Non-required0.6848
Model Value Unit
Absorption
Aqueous solubility-3.7498LogS
Caco-2 Permeability1.9866LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0905LD50, mol/kg
Fish Toxicity1.0450pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3236pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.01*04/01/2018
Elderberries (Bayberries, Buffalo berries, Che berries, Dwarf elderberries, Guelder rose berries, Hawberries, Midland hawberries, Phalsa fruits, Riberries, Rowan berries, Saskatoons/saskatoons berr...0154080European Union0.01*04/01/2018
Horseradishes (Dandelion roots, Gentiana roots, East Indian galangal/aromatic ginger/sand galangal, Fingerroot, Galangal roots, Galangal roots, Galangal roots, Galangal roots, Ginger roots, Greater...0213040European Union0.01*04/01/2018
Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou...0251040European Union0.01*04/01/2018
Other NutsJapan0.03ppm
WalnutJapan0.01ppm
AlmondJapan0.01ppm
PecanJapan0.01ppm
ChestnutJapan0.01ppm
Ginkgo NutJapan0.01ppm
GrapeAustria0. 5mg/kg
Milk & Dairy ProduceBritain0.001mg/kg
Sweet CornBritain0.01mg/kg
Mandarins (Inc Clementines & Similar Hybrids)Britain0.01mg/kg
SalmoniformesJapan1ppm
Other Poultry Animals,LiverJapan0.01ppm
Other Umbelliferous VegetablesJapan1ppm
Lettuce(Including Cos Lettuce And Leaf Lettuce)Japan2ppm
TomatoSingapore3mg/kg
Brussels SproutsSingapore0. 5mg/kg

References

TitleJournalDatePubmed ID
Tracking residual organochlorine pesticides (OCPs) in green, herbal, and blacktea leaves and infusions of commercially available tea products marketed inPoland.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018Mar29210611
Stereoselective accumulations of hexachlorocyclohexanes (HCHs) are correlated with Sphingomonas spp. in agricultural soils across China.Environ Pollut2018 Sep29729566
Persistent organochlorine pesticides in aquatic environments and fishes in Taiwan and their risk assessment.Environ Sci Pollut Res Int2018 Mar29288298
Dietary exposure to HCH and DDT congeners and their associated cancer risk based on Pakistani food consumption.Environ Sci Pollut Res Int2018 Mar29307071
Serum concentrations of organochlorine compounds and predictors of exposure inchildren living in agricultural communities from South-Eastern Spain.Environ Pollut2018 Jun29129429
Biomagnification and enantiomeric profiles of organochlorine pesticides in foodweb components from Zhoushan Fishing Ground, China.Mar Pollut Bull2018 Jun29886987
First evaluation of the use of down feathers for monitoring persistent organicpollutants and organophosphate ester flame retardants: A pilot study usingnestlings of the endangered cinereous vulture (Aegypius monachus).Environ Pollut2018 Jul29587212
Selective bioaccumulation, biomagnification, and dissipation ofhexachlorocyclohexane isomers in a freshwater food chain.Environ Sci Pollut Res Int2018 Jul29713971
Determinants of serum organochlorine pesticide and polychlorinated biphenyllevels in middle-aged Korean adults.Environ Sci Pollut Res Int2018 Jan29032525
[Residue Levels and Health Risk Assessment of Organochlorine Pesticides in Ricefrom Shanghai].Huan Jing Ke Xue2018 Feb 829964859
Transplacental transfer characteristics of organochlorine pesticides in pairedmaternal and cord sera, and placentas and possible influencing factors.Environ Pollut2018 Feb29100182
Distribution and risk assessment of banned and other current-use pesticides insurface and groundwaters consumed in an agricultural catchment dominated by cocoacrops in the Ankobra Basin, Ghana.Sci Total Environ2018 Aug 1529597160
Organochlorine pesticides (OCPs) and polychlorinated biphenyls (PCBs) inCyprinidae fish: Towards hints of their arrangements using advancedclassification methods.Environ Res2018 Aug29783084
Background biomonitoring of residue levels of 137 pesticides in the blood plasma of the general population in Beijing.Environ Monit Assess2018 Apr 2929705822
Residue behavior of organochlorine pesticides during the production process ofyogurt and cheese.Food Chem2018 Apr 1529287340
[Determination of S-421 in Commercial Fish and Shellfish].Shokuhin Eiseigaku Zasshi201829743468
Gas chromatography-tandem mass spectrometry multi-residual analysis ofcontaminants in Italian honey samples.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017May28277179
Assessment of pesticide residues in vegetables from the Western Usambara andUruguru Mountains in Tanzania.Environ Monit Assess2017 Sep 2528948449
Neonatal exposure to environmental pollutants and placental mitochondrial DNA content: A multi-pollutant approach.Environ Int2017 Sep28600986
Measurements of β and α hexachlorocyclohexane in Juglans regia and Prunus spinosa trees in a contaminated area, central Italy.Environ Sci Pollut Res Int2017 Sep28721619