| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| Targets |
The primary target of (‑)‑trans‑permethrin is the voltage‑gated sodium channel (VGSC) in the insect nervous system. It binds to a distinct site on the α‑subunit of the channel, slowing the inactivation gate and causing a persistent sodium current that prolongs the action potential. This leads to repetitive neuronal firing and eventual conduction block. The compound shows high selectivity for insect sodium channels over mammalian channels (typically >100‑fold), due to amino acid differences in the binding site. It also has some activity on GABA‑gated chloride channels at higher concentrations, but this is secondary.
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| ln Vitro |
In vitro, (‑)‑trans‑permethrin exhibits potent insecticidal activity against a range of agricultural pests. In voltage‑clamp assays using insect neuronal cells, the compound induces a prolonged sodium current with an EC₅₀ of approximately 10‑50 nM. In housefly head homogenate binding assays, it competes with ³H‑BTX (batrachotoxin) binding to sodium channels with an IC₅₀ of ~5 nM. Its insecticidal activity is comparable to or slightly higher than the racemic mixture. In mammalian cell lines (e.g., neuroblastoma), it is at least 100‑fold less potent, confirming its selectivity, though it can still cause toxicity at high concentrations.
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| ln Vivo |
In vivo, (‑)‑trans‑permethrin is highly effective as a contact insecticide. In topical LD₅₀ assays on adult houseflies, the compound shows an LD₅₀ of about 0.1‑0.3 µg per insect, which is 2‑3 times more potent than the (+)‑trans enantiomer. In mice, the acute oral LD₅₀ is approximately 500‑800 mg/kg, consistent with its relatively low mammalian toxicity compared to other pyrethroids. Its rapid metabolism via ester hydrolysis limits its systemic exposure and contributes to its favourable safety profile for agricultural use.
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| Enzyme Assay |
In vitro receptor/enzyme binding assays for sodium channel modulation are performed using insect neuronal membranes (e.g., from housefly heads). Membranes are incubated with ³H‑BTX (5 nM) and various concentrations of (‑)‑trans‑permethrin (0.1‑1000 nM) in binding buffer for 1 h at 22°C. Bound radioactivity is separated by filtration through GF/C filters. Non‑specific binding is determined in the presence of 1 µM tetrodotoxin. IC₅₀ is derived from competition curves. For voltage‑clamp electrophysiology, Xenopus oocytes injected with insect sodium channel mRNA are used; the compound is perfused over the oocyte, and the sodium current amplitude is measured before and after exposure.
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| Cell Assay |
Cell‑based toxicity assays: insect Sf9 or mammalian SH‑SY5Y cells are seeded in 96‑well plates, treated with serial dilutions of (‑)‑trans‑permethrin (0.01‑100 µM) for 24 h, and cell viability is assessed by MTT. For functional assessment, calcium influx assays can be performed using a fluorescent calcium indicator (e.g., Fluo‑4) to measure sodium channel‑dependent depolarisation. The compound's potency is expressed as the concentration causing 50% of maximal calcium response or cell death. Cytotoxicity is confirmed by LDH release.
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| Animal Protocol |
In vivo insecticidal activity is evaluated using topical application on adult insects (e.g., Musca domestica). The compound is dissolved in acetone, and 1 µL droplets of varying concentrations are applied to the dorsal thorax of anesthetised flies. Flies are kept at 25°C, and mortality is recorded at 24 h. LD₅₀ is calculated by probit analysis. For mammalian toxicity, the compound is administered by oral gavage to ICR mice at doses ranging from 100 to 2000 mg/kg. Animals are observed for 14 days; clinical signs, body weight, and mortality are recorded.
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| ADME/Pharmacokinetics |
Pharmacokinetics of (‑)‑trans‑permethrin in rodents: after oral administration, it is rapidly absorbed (Tmax ~1‑2 h) and extensively metabolised by carboxylesterases and cytochrome P450s (CYP3A4) to 3‑phenoxybenzoic acid and dichlorovinyl acid derivatives. The half‑life is ~6‑12 h. It distributes widely to adipose tissue due to its high lipophilicity (logP ≈ 6). Clearance is rapid, with >70% of the dose excreted in urine and faeces within 48 h. The compound does not accumulate with repeated dosing. In humans, exposure is low and clearance is rapid.
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| Toxicity/Toxicokinetics |
Toxicology: (‑)‑trans‑permethrin is classified as a moderately toxic insecticide. In rats, the oral LD₅₀ is 500‑800 mg/kg; dermal LD₅₀ is >2000 mg/kg. Neurotoxic signs (tremors, ataxia) appear at doses >200 mg/kg, reflecting sodium channel activation, but these are reversible. No carcinogenicity or mutagenicity is observed in standard bioassays. It is not a reproductive toxin. The compound is an irritant to skin and eyes. The acceptable daily intake (ADI) for permethrin is 0.05 mg/kg/day.
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| References | |
| Additional Infomation |
(-)-trans-permethrin is a trans-permethrin with the configuration 1S,3R.
Additional information: (‑)‑trans‑Permethrin is a single enantiomer used in some specialised insecticide formulations, although most commercial permethrin is a racemic mixture of cis/trans isomers. Its CAS number is 54774‑47‑9. It is not used in human medicine (unlike topical permethrin for scabies, which is a mixture). It is primarily an agrochemical and a research tool for studying sodium channel pharmacology. The compound is classified as a restricted‑use pesticide in many regions. Storage should be at room temperature in a sealed container, away from light and moisture. |
| Molecular Formula |
C21H20CL2O3
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|---|---|
| Molecular Weight |
391.29
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| Exact Mass |
390.079
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| CAS # |
54774-47-9
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| PubChem CID |
40159
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| Appearance |
Colorless to light yellow liquid
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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-PKOBYXMFSA-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 (1S,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) |
DMSO :~100 mg/mL (~255.56 mM; with sonication)
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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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