An insecticide and GABAA receptor antagonist
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Metabolite(s)
297432,3,4,5-Tetrachlorophenol
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γ-Lindane

Item No. 23952

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1α,2α,3β,4α,5α,6β-hexachloro-cyclohexane
CAS Number
58-89-9
Molecular Formula
C6H6Cl6
Formula Weight
290.8
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 50 mg/mlEthanol: >1 mg/mlMethanol: >1 mg/mlWater: 8.35 mg/ml
SMILES
Cl[C@@H]1[C@@H](Cl)[C@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl
InChi Code
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 Key
JLYXXMFPNIAWKQ-GNIYUCBRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    γ-Lindane is an organochloro insecticide that is an antagonist of GABAA receptors.1 It inhibits GABA-stimulated chloride uptake by membrane vesicles isolated from rat cerebral cortex (IC50 = 68 μM). It binds selectively to insect GABAA receptors over mammalian GABAA receptors in membrane preparations (IC50s = 1, 12, 505, 833, and 150-1, 675 nM for fruit fly, house fly, human, mouse, and rat, respectively).2,3 It binds to a human recombinant β3 homooligomer with similar selectivity as α1β3γ2-containing receptors, indicating that the binding site for γ-lindane on GABAA receptors is located on the β3 subunit (IC50s = 0.90, 21, and 306 nM for β3, α1β3γ2, and the native receptor, respectively).4 γ-Lindane blocks GABA- and glutamate-induced current responses in American cockroach neurons (IC50s = 1.74 and 148 nM, respectively).5 It is toxic to mice and adult house flies (LD50s = 40 and 5.5 mg/kg, respectively) and also kills head lice in vitro and inhibits hatching.4,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Obata, T., Yamamura, H.I., Malatynska, E., et al. Modulation of ɤ-aminobutyric acid-stimulated chloride influx by bicycloorthocarboxylates, bicyclophosphorus esters, polychlorocycloalkanes and other cage convulsants. J. Pharmacol. Exp. Ther. 244(3), 802-806 (1988).

    2. Hainzl, D., Cole, L.M., and Casida, J.E. Mechanisms for selective toxicity of fipronil insecticide and its sulfone metabolite and desulfinyl photoproduct. Chem. Res. Toxicol. 11(12), 1529-1535 (1998).

    3. Llorens, J., Suñol, C., Tussel, J.M., et al. Lindane inhibition of [35S]TBPS binding to the GABAA receptor in rat brain. Neurotoxicol. Teratol. 12(6), 607-610 (1990).

    4. Ratra, G.S., Kamita, S.G., and Casida, J.E. Role of human GABAA receptor β3 subunit in insecticide toxicity. Toxicol. Appl. Pharmacol. 172(3), 233-240 (2001).

    5. Ihara, M., Ishida, C., Okuda, H., et al. Differential blocking actions of 4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB) and ɤ-hexachlorocyclohexane (ɤ-HCH) on ɤ-aminobutyric acid- and glutamate-induced responses of American cockroach neurons. Invert. Neurosci. 5(3-4), 157-164 (2005).

    6. Meinking, T.L., Taplin, D., Kalter, D.C., et al. Comparative efficacy of treatments for pediculosis capitis infestations. Arch. Dermatol. 122(3), 267-271 (1986).