| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
1R‑cis‑Permethrin targets the voltage‑gated sodium channel (VGSC) in insects, binding to the same receptor site as other pyrethroids. The cis configuration allows a more favourable interaction with the channel, often leading to a slower dissociation rate and thus longer‑lasting channel modification. Its affinity (KD) for housefly sodium channels is approximately 1‑3 nM, similar to or slightly higher than the trans isomers. It also shows a modest activity on GABA receptors, but the sodium channel is the dominant toxicological target. The stereospecificity is evident in its higher potency against lepidopteran pests compared to trans isomers.
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| ln Vitro |
In vitro, 1R‑cis‑permethrin is a potent inhibitor of ³H‑BTX binding to insect sodium channels, with an IC₅₀ of approximately 2‑5 nM. In whole‑cell patch‑clamp on Drosophila neurons, it induces a characteristic tail current after depolarisation, with an EC₅₀ of ~5 nM. In mammalian cells, it is considerably less potent (IC₅₀ >1 µM). The compound shows anti‑proliferative effects in insect cell lines with IC₅₀ values of 0.5‑2 µM. Its stability in biological matrices is higher than trans isomers due to slower esterase hydrolysis, which contributes to its persistence.
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| ln Vivo |
In vivo, 1R‑cis‑permethrin exhibits a topical LD₅₀ of about 0.05‑0.1 µg per housefly, making it one of the most potent pyrethroid isomers. In rats, the oral LD₅₀ is approximately 200‑300 mg/kg, which is lower (more toxic) than the trans isomers, reflecting the cis configuration's higher affinity for mammalian sodium channels. In agricultural applications, it provides excellent residual activity. In a mouse model of permethrin poisoning, the cis isomer induces more severe and prolonged clinical signs (tremor, choreoathetosis) than trans isomers at equivalent doses.
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| Enzyme Assay |
In vitro binding assays: insect head membranes (100 µg protein) are incubated with ³H‑BTX (5 nM) and unlabelled 1R‑cis‑permethrin (0.1‑100 nM) in 10 mM HEPES buffer (pH 7.4) with 0.1% BSA for 60 min. Filtration and counting determine bound radioactivity. IC₅₀ values are derived. For metabolic stability, the compound is incubated with rat liver microsomes (0.5 mg/mL) and NADPH at 37°C; remaining parent compound is quantified by HPLC at 0, 10, 20, 40, 60 min to calculate half‑life. The cis isomer is typically metabolised 2‑3 times slower than trans.
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| Cell Assay |
Cell‑based assays use SH‑SY5Y human neuroblastoma cells to assess mammalian cytotoxicity. Cells are treated with 0.01‑100 µM compound for 48 h; viability is measured by CellTiter‑Glo. The IC₅₀ is typically 20‑50 µM, higher than in insects. For functional sodium channel assay, insect Sf9 cells expressing the Drosophila para sodium channel are used. A fluorescent membrane potential dye is applied, and cells are stimulated; the compound's effect on repolarisation kinetics is recorded in a plate reader format. The EC₅₀ for potentiating depolarisation is calculated.
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| Animal Protocol |
In vivo insect bioassays: adult houseflies are anaesthetised with CO₂ and dosed topically with 0.5 µL of acetone solutions (0.01‑1 µg). Mortality is scored at 4, 8, 24, and 48 h. For mammals, Sprague‑Dawley rats are dosed orally (50‑400 mg/kg) with the compound in corn oil and observed for 14 days. The LD₅₀ and clinical signs are recorded. Tissue samples (brain, liver, fat) are collected at sacrifice for residue analysis using GC‑MS to determine tissue distribution.
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| ADME/Pharmacokinetics |
Pharmacokinetics in rats: 1R‑cis‑permethrin is absorbed with a Tmax of 2‑4 h and exhibits a longer half‑life than trans isomers (approximately 12‑24 h) due to slower ester cleavage. It has high lipophilicity (logP 6.5) and distributes extensively to adipose tissue. Metabolism is via CYP‑mediated oxidation (mainly at the methyl groups) followed by conjugation. Excretion is predominantly in faeces (>80%), with less in urine. The cis isomer shows higher potential for tissue accumulation with repeated dosing compared to trans.
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| Toxicity/Toxicokinetics |
Toxicology: the cis isomer is more neurotoxic to mammals than trans; the oral LD₅₀ in rats is 200‑400 mg/kg, compared to 500‑1000 mg/kg for trans. Single high doses cause tremors, salivation, and hyperthermia. No carcinogenicity is seen in chronic studies. The compound is also more toxic to fish (LC₅₀ 0.5‑2 ppb), reflecting its persistence. It is a moderate skin irritant. The acceptable operator exposure limit (AOEL) for permethrin (as a mixture) accounts for the cis isomer's greater toxicity.
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| References | |
| Additional Infomation |
pyrethroid insecticide commonly used to treat lice infestations and scabies.
Additional information: 1R‑cis‑Permethrin (CAS 54774‑45‑7) is one of the most potent insecticidal isomers and is a key component of many commercial permethrin formulations, which typically contain 20‑40% cis and 60‑80% trans isomers. The cis content significantly influences the overall efficacy and mammalian toxicity of the mixture. It is a pale yellow liquid at room temperature. It is not used as a standalone therapeutic agent. Its research applications include studies on insecticide resistance and sodium channel mutations. Storage should be at 4°C in the dark to prevent photodegradation. |
| Molecular Formula |
C21H20CL2O3
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|---|---|
| Molecular Weight |
391.29
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| Exact Mass |
390.079
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| CAS # |
54774-45-7
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| PubChem CID |
40463
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| Appearance |
White to off-white solid powder
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| Density |
1.293g/cm3
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| Boiling Point |
200ºC at 0.1 mmHg; >290ºC at 760 mmHg
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| Melting Point |
34-35ºC
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| Flash Point |
159.4ºC
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| LogP |
6.113
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
26
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| Complexity |
521
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC1([C@H]([C@H]1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
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| InChi Key |
RLLPVAHGXHCWKJ-HKUYNNGSSA-N
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| 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/t17-,19-/m0/s1
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| Chemical Name |
(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
Typically soluble in DMSO (e.g. 10 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5556 mL | 12.7782 mL | 25.5565 mL | |
| 5 mM | 0.5111 mL | 2.5556 mL | 5.1113 mL | |
| 10 mM | 0.2556 mL | 1.2778 mL | 2.5556 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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