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MedKoo Cat#: 318473 | Name: Permethrin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Permethrin is a widely-used pesticide of the pyrethroid family. Permethrin interacts with voltage-gated Na+ channels and inhibits their natural deactivation, causing the channels to remain open for a long time and destroying equilibrium of the neuronal system. Pyrethroids are also thought to interact with GABA receptors and associated pathways.

Chemical Structure

Permethrin
CAS#52645-53-1

Theoretical Analysis

MedKoo Cat#: 318473

Name: Permethrin

CAS#: 52645-53-1

Chemical Formula: C21H20Cl2O3

Exact Mass: 390.0790

Molecular Weight: 391.29

Elemental Analysis: C, 64.46; H, 5.15; Cl, 18.12; O, 12.27

Price and Availability

Size Price Availability Quantity
100mg USD 150.00
200mg USD 250.00
500mg USD 450.00
1g USD 650.00
2g USD 850.00
5g USD 1,250.00
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Synonym
Permethrin; Transpermethrin; 1RS,cis-Permethrin; 1RS-trans-Permethrin; Transpermethrin [ISO]; cis-permethrin; Elimite; FMC 33297; S-3151; S3151;
IUPAC/Chemical Name
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
InChi Key
RLLPVAHGXHCWKJ-UHFFFAOYSA-N
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
SMILES Code
CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Permethrin (NRDC-143) is an insecticide, acaricide, and insect repellent; functions as a neurotoxin, affecting neuron membranes by prolonging sodium channel activation.
In vitro activity:
The objective of this pilot study is to investigate the in vitro effects of permethrin on sinonasal epithelial cells (SNECs). Cultured SNECs were exposed to varied concentrations of permethrin (0-156 µM) for 6 days. A statistically significant reduction in cell viability and proliferation was observed between the exposure and control groups at certain concentrations, and a dose-dependent increase in ROS activity was also observed. These findings indicate that permethrin may have deleterious effects on SNECs in a dose-dependent manner. Reference: OTO Open. 2022 Jul 14;6(3):2473974X221109838. https://pubmed.ncbi.nlm.nih.gov/35860617/
In vivo activity:
The purpose of this study was to investigate the effects and interactions of permethrin exposure (50, 500, and 5000 μg/kg body weight/day) and dietary fat (low fat, 4% w/w; high fat, 20% w/w) on development of obesity and insulin resistance in male C57BL/6J mice. These results showed that permethrin treatment significantly increased body weight, fat mass, and insulin resistance with high fat diet, but not with low fat diet, without influencing energy intake. Permethrin treatment also significantly increased serum levels of insulin, glucose, leptin, triglycerides and cholesterol. Further results showed that permethrin inhibited AMP-activated protein kinase in white adipose tissue. Reference: Food Chem Toxicol. 2018 Jan;111:405-416. https://pubmed.ncbi.nlm.nih.gov/29175578/
Solvent mg/mL mM comments
Solubility
DMF 33.0 84.34
DMSO 48.0 122.67
Ethanol 16.5 42.17
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 391.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lee HS, Song HJ, Park Y, Smolensky D, Lee SH. Permethrin inhibits tube formation and viability of endothelial cells. J Sci Food Agric. 2022 Aug 15;102(10):4079-4085. doi: 10.1002/jsfa.11757. Epub 2022 Jan 22. PMID: 34997580. 2. Lee JT, Yang HH, Sanghoon Shin D, Srivatsan E, Basak S. In Vitro Effects of Permethrin on Sinonasal Epithelia. OTO Open. 2022 Jul 14;6(3):2473974X221109838. doi: 10.1177/2473974X221109838. PMID: 35860617; PMCID: PMC9289904. 3. Aoiadni N, Chiab N, Jdidi H, Gargouri Bouzid R, El Feki A, Fetoui H, Ghorbel Koubaa F. The pyrethroid insecticide permethrin confers hepatotoxicity through DNA damage and mitochondria-associated apoptosis induction in rat: Palliative benefits of Fumaria officinalis. J Biochem Mol Toxicol. 2022 Oct;36(10):e23172. doi: 10.1002/jbt.23172. Epub 2022 Jul 21. PMID: 35861702. 4. Xiao X, Sun Q, Kim Y, Yang SH, Qi W, Kim D, Yoon KS, Clark JM, Park Y. Exposure to permethrin promotes high fat diet-induced weight gain and insulin resistance in male C57BL/6J mice. Food Chem Toxicol. 2018 Jan;111:405-416. doi: 10.1016/j.fct.2017.11.047. Epub 2017 Nov 23. PMID: 29175578; PMCID: PMC5756676.
In vitro protocol:
1. Lee HS, Song HJ, Park Y, Smolensky D, Lee SH. Permethrin inhibits tube formation and viability of endothelial cells. J Sci Food Agric. 2022 Aug 15;102(10):4079-4085. doi: 10.1002/jsfa.11757. Epub 2022 Jan 22. PMID: 34997580. 2. Lee JT, Yang HH, Sanghoon Shin D, Srivatsan E, Basak S. In Vitro Effects of Permethrin on Sinonasal Epithelia. OTO Open. 2022 Jul 14;6(3):2473974X221109838. doi: 10.1177/2473974X221109838. PMID: 35860617; PMCID: PMC9289904.
In vivo protocol:
1. Aoiadni N, Chiab N, Jdidi H, Gargouri Bouzid R, El Feki A, Fetoui H, Ghorbel Koubaa F. The pyrethroid insecticide permethrin confers hepatotoxicity through DNA damage and mitochondria-associated apoptosis induction in rat: Palliative benefits of Fumaria officinalis. J Biochem Mol Toxicol. 2022 Oct;36(10):e23172. doi: 10.1002/jbt.23172. Epub 2022 Jul 21. PMID: 35861702. 2. Xiao X, Sun Q, Kim Y, Yang SH, Qi W, Kim D, Yoon KS, Clark JM, Park Y. Exposure to permethrin promotes high fat diet-induced weight gain and insulin resistance in male C57BL/6J mice. Food Chem Toxicol. 2018 Jan;111:405-416. doi: 10.1016/j.fct.2017.11.047. Epub 2017 Nov 23. PMID: 29175578; PMCID: PMC5756676.
1: Tu W, Xu C, Jin Y, Lu B, Lin C, Wu Y, Liu W. Permethrin is a potential thyroid-disrupting chemical: In vivo and in silico envidence. Aquat Toxicol. 2016 Mar 9;175:39-46. doi: 10.1016/j.aquatox.2016.03.006. [Epub ahead of print] PubMed PMID: 26994367. 2: Willemin ME, Desmots S, Le Grand R, Lestremau F, Zeman FA, Leclerc E, Moesch C, Brochot C. PBPK modeling of the cis- and trans-permethrin isomers and their major urinary metabolites in rats. Toxicol Appl Pharmacol. 2016 Mar 1;294:65-77. doi: 10.1016/j.taap.2016.01.011. Epub 2016 Jan 20. PubMed PMID: 26802525. 3: Faulde MK, Pages F, Uedelhoven W. Bioactivity and laundering resistance of five commercially available, factory-treated permethrin-impregnated fabrics for the prevention of mosquito-borne diseases: the need for a standardized testing and licensing procedure. Parasitol Res. 2016 Apr;115(4):1573-82. doi: 10.1007/s00436-015-4892-2. Epub 2016 Jan 7. PubMed PMID: 26738734. 4: Becskei C, Geurden T, Erasmus H, Cuppens O, Mahabir SP, Six RH. Comparative speed of kill after treatment with Simparica(™)(sarolaner) and Advantix(®)(imidacloprid + permethrin) against induced infestations of Dermacentor reticulatus on dogs. Parasit Vectors. 2016 Feb 24;9(1):104. doi: 10.1186/s13071-016-1377-9. PubMed PMID: 26911323; PubMed Central PMCID: PMC4765083. 5: Nasuti C, Coman MM, Olek RA, Fiorini D, Verdenelli MC, Cecchini C, Silvi S, Fedeli D, Gabbianelli R. Changes on fecal microbiota in rats exposed to permethrin during postnatal development. Environ Sci Pollut Res Int. 2016 Feb 22. [Epub ahead of print] PubMed PMID: 26898931. 6: Halos L, Fourie JJ, Fankhauser B, Beugnet F. Knock-down and speed of kill of a combination of fipronil and permethrin for the prevention of Ctenocephalides felis flea infestation in dogs. Parasit Vectors. 2016 Feb 2;9(1):57. doi: 10.1186/s13071-016-1345-4. PubMed PMID: 26830931; PubMed Central PMCID: PMC4736277. 7: Mostafa HE, Abd El-Baset SA, Kattaia AA, Zidan RA, Al Sadek MM. Efficacy of naringenin against permethrin-induced testicular toxicity in rats. Int J Exp Pathol. 2016 Feb 12. doi: 10.1111/iep.12168. [Epub ahead of print] PubMed PMID: 26867500. 8: Seitz MA, Burkitt-Creedon JM. Persistent gross lipemia and suspected corneal lipidosis following intravenous lipid therapy in a cat with permethrin toxicosis. J Vet Emerg Crit Care (San Antonio). 2016 Jan 8. doi: 10.1111/vec.12440. [Epub ahead of print] PubMed PMID: 26748969. 9: Whiten SR, Peterson RK. The Influence of Ambient Temperature on the Susceptibility of Aedes aegypti (Diptera: Culicidae) to the Pyrethroid Insecticide Permethrin. J Med Entomol. 2016 Jan;53(1):139-43. doi: 10.1093/jme/tjv159. PubMed PMID: 26477050. 10: Rossbach B, Kegel P, Süß H, Letzel S. Biomonitoring and evaluation of permethrin uptake in forestry workers using permethrin-treated tick-proof pants. J Expo Sci Environ Epidemiol. 2016 Jan;26(1):95-103. doi: 10.1038/jes.2015.34. Epub 2015 May 13. PubMed PMID: 25967068. 11: Ratelle M, Coté J, Bouchard M. Time profiles and toxicokinetic parameters of key biomarkers of exposure to cypermethrin in orally exposed volunteers compared with previously available kinetic data following permethrin exposure. J Appl Toxicol. 2015 Dec;35(12):1586-93. doi: 10.1002/jat.3124. Epub 2015 Mar 13. PubMed PMID: 25772368. 12: Li T, Cao C, Yang T, Zhang L, He L, Xi Z, Bian G, Liu N. A G-protein-coupled receptor regulation pathway in cytochrome P450-mediated permethrin-resistance in mosquitoes, Culex quinquefasciatus. Sci Rep. 2015 Dec 10;5:17772. doi: 10.1038/srep17772. PubMed PMID: 26656663; PubMed Central PMCID: PMC4674712. 13: Brinzer RA, Henderson L, Marchiondo AA, Woods DJ, Davies SA, Dow JA. Metabolomic profiling of permethrin-treated Drosophila melanogaster identifies a role for tryptophan catabolism in insecticide survival. Insect Biochem Mol Biol. 2015 Dec;67:74-86. doi: 10.1016/j.ibmb.2015.09.009. Epub 2015 Oct 22. PubMed PMID: 26474926. 14: Chen X, Li H, You J. Joint toxicity of sediment-associated permethrin and cadmium to Chironomus dilutus: The role of bioavailability and enzymatic activities. Environ Pollut. 2015 Dec;207:138-44. doi: 10.1016/j.envpol.2015.09.012. Epub 2015 Sep 12. PubMed PMID: 26367707. 15: Terhzaz S, Cabrero P, Brinzer RA, Halberg KA, Dow JA, Davies SA. A novel role of Drosophila cytochrome P450-4e3 in permethrin insecticide tolerance. Insect Biochem Mol Biol. 2015 Dec;67:38-46. doi: 10.1016/j.ibmb.2015.06.002. Epub 2015 Jun 12. PubMed PMID: 26073628; PubMed Central PMCID: PMC4673087. 16: Jongejan F, de Vos C, Fourie JJ, Beugnet F. A novel combination of fipronil and permethrin (Frontline Tri-Act®/Frontect®) reduces risk of transmission of Babesia canis by Dermacentor reticulatus and of Ehrlichia canis by Rhipicephalus sanguineus ticks to dogs. Parasit Vectors. 2015 Nov 19;8:602. doi: 10.1186/s13071-015-1207-5. PubMed PMID: 26586365; PubMed Central PMCID: PMC4653891. 17: Ferland S, Côté J, Ratelle M, Thuot R, Bouchard M. Detailed Urinary Excretion Time Courses of Biomarkers of Exposure to Permethrin and Estimated Exposure in Workers of a Corn Production Farm in Quebec, Canada. Ann Occup Hyg. 2015 Nov;59(9):1152-67. doi: 10.1093/annhyg/mev059. Epub 2015 Aug 31. PubMed PMID: 26324827. 18: Dumont P, Liebenberg J, Beugnet F, Fankhauser B. Repellency and acaricidal efficacy of a new combination of fipronil and permethrin against Ixodes ricinus and Rhipicephalus sanguineus ticks on dogs. Parasit Vectors. 2015 Oct 13;8:531. doi: 10.1186/s13071-015-1150-5. PubMed PMID: 26463998; PubMed Central PMCID: PMC4605137. 19: Eiden AL, Kaufman PE, Allan SA, Oi F. Establishing the discriminating concentration for permethrin and fipronil resistance in Rhipicephalus sanguineus (Latreille) (Acari: Ixodidae), the brown dog tick. Pest Manag Sci. 2015 Oct 9. doi: 10.1002/ps.4165. [Epub ahead of print] PubMed PMID: 26449370. 20: DeRaedt Banks S, Orsborne J, Gezan SA, Kaur H, Wilder-Smith A, Lindsey SW, Logan JG. Permethrin-Treated Clothing as Protection against the Dengue Vector, Aedes aegypti: Extent and Duration of Protection. PLoS Negl Trop Dis. 2015 Oct 6;9(10):e0004109. doi: 10.1371/journal.pntd.0004109. eCollection 2015 Oct. PubMed PMID: 26440967; PubMed Central PMCID: PMC4595206.