A modulator of voltage-gated sodium channels
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Analytical Standard(s)
39355Permethrin (CRM)
Labeled Version(s)
39585Permethrin-d9
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Permethrin

Item No. 23821

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropanecarboxylic acid, (3-phenoxyphenyl)methyl ester
CAS Number
52645-53-1
Molecular Formula
C21H20Cl2O3
Formula Weight
391.3
Purity
≥95% (mixture of isomers)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 16 mg/mlEthanol: 14 mg/ml
SMILES
O=C(C1C(C)(C)C1/C=C(Cl)/Cl)OCC2=CC(OC3=CC=CC=C3)=CC=C2
InChi Code
InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3
InChi Key
RLLPVAHGXHCWKJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $41

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    Cayman Chemical
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    Product Description

    Permethrin is a modulator of voltage-gated sodium channels (NaV) that is used as an insecticide.1 It delays channel deactivation of the NaV1.8 channel expressed in X. laevis oocytes. It is at least 100-fold more potent at insect than mammalian sodium channels, leading to slow deactivation of D. para/TipE, but not rat brain IIA or β1, sodium channels expressed in X. laevis oocytes when used at a concentration of 500 nM.2 Permethrin (5 µM) increases sodium influx in BV-2 and primary microglial cells by approximately 28 and 29%, respectively, and activates microglia.3 Long-term application of permethrin leads to dose- and time-dependent intracellular sodium accumulation and TNF-α release in microglia in vitro. Formulations containing permethrin have been used for the treatment of head lice and scabies infestations.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Choi, J.S., and Soderlund, D.M. Structure-activity relationships for the action of 11 pyrethroid insecticides on rat Nav1.8 sodium channels expressed in Xenopus oocytes. Toxicol. Appl. Pharmacol. 211(3), 233-244 (2006).

    2. Warmke, J.W., Reenan, R.A., Wang, P., et al. Functional expression of Drosophila para sodium channels. Modulation by the membrane protein TipE and toxin pharmacology. J. Gen. Physiol. 110(2), 119-133 (1997).

    3. Hossain, M.M., Liu, J., and Richardson, J.R. Pyrethroid insecticides directly activate microglia through interaction with voltage-gated sodium channels. Toxicol. Sci. 155(1), 112-123 (2017).