Tetramethrin
(Synonyms: 胺菊酯) 目录号 : GC39684
Tetramethrin 是一种合成的拟除虫菊酯类杀虫剂，可用于多种害虫。
Cas No.:7696-12-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Tetramethrin is a synthetic pyrethroid insecticide for use on a broad spectrum of insect pests[1].
[1]. Pengfei Zhao,et al. Stereoselective Analysis of Chiral Pyrethroid Insecticides Tetramethrin and α-Cypermethrin in Fruits, Vegetables, and Cereals. J Agric Food Chem. 2019 Aug 21;67(33):9362-9370.
| Cas No. | 7696-12-0 | SDF | |
| 别名 | 胺菊酯 | ||
| Canonical SMILES | O=C(OCN(C1=O)C(C2=C1CCCC2)=O)C3C(C)(C3/C=C(C)\C)C | ||
| 分子式 | C19H25NO4 | 分子量 | 331.41 |
| 溶解度 | DMSO : 25 mg/mL (75.44 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0174 mL | 15.0871 mL | 30.1741 mL |
| 5 mM | 0.6035 mL | 3.0174 mL | 6.0348 mL |
| 10 mM | 0.3017 mL | 1.5087 mL | 3.0174 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Ecotoxicity evaluation of Tetramethrin and analysis in agrochemical formulations using chiral electrokinetic chromatography
Sci Total Environ 2021 Dec 15;800:149496.PMID:34388647DOI:10.1016/j.scitotenv.2021.149496.
The separation of the four isomers of Tetramethrin was performed for the first time using a cyclodextrin-micellar electrokinetic chromatography methodology. Using sodium deoxycholate and 2-hydroxypropyl-β-CD as chiral selectors, Tetramethrin isomers were separated with resolution values of 1.7 and 1.1 for trans- and cis-isomers, respectively, in analysis times lower than 12.5 min. Once developed and optimized, the analytical method was applied to the analysis of an antiparasitic commercial formulation and to the evaluation of the stability and ecotoxicity of Tetramethrin. Using measured concentrations, the stability was assessed at enantiomeric level and the ecotoxicological parameters on Daphnia magna were determined. Tetramethrin presents toxicity on aquatic microinvertebrates, with EC50 (t = 72 h) of 1.8 mg/L. The acute toxicity of tetrametrin was attributed to the trans-1 enantiomer. The first evidence of oxidative stress-mediated mode of action for Tetramethrin on Daphnia magna is reported in the present work.
Novel Mechanism and Kinetics of Tetramethrin Degradation Using an Indigenous Gordonia cholesterolivorans A16
Int J Mol Sci 2021 Aug 26;22(17):9242.PMID:34502147DOI:10.3390/ijms22179242.
Tetramethrin is a pyrethroid insecticide that is commonly used worldwide. The toxicity of this insecticide into the living system is an important concern. In this study, a novel tetramethrin-degrading bacterial strain named A16 was isolated from the activated sludge and identified as Gordonia cholesterolivorans. Strain A16 exhibited superior Tetramethrin degradation activity, and utilized Tetramethrin as the sole carbon source for growth in a mineral salt medium (MSM). High-performance liquid chromatography (HPLC) analysis revealed that the A16 strain was able to completely degrade 25 mg·L-1 of Tetramethrin after 9 days of incubation. Strain A16 effectively degraded Tetramethrin at temperature 20-40 °C, pH 5-9, and initial Tetramethrin 25-800 mg·L-1. The maximum specific degradation rate (qmax), half-saturation constant (Ks), and inhibition constant (Ki) were determined to be 0.4561 day-1, 7.3 mg·L-1, and 75.2 mg·L-1, respectively. The Box-Behnken design was used to optimize degradation conditions, and maximum degradation was observed at pH 8.5 and a temperature of 38 °C. Five intermediate metabolites were identified after analyzing the degradation products through gas chromatography-mass spectrometry (GC-MS), which suggested that Tetramethrin could be degraded first by cleavage of its carboxylester bond, followed by degradation of the five-carbon ring and its subsequent metabolism. This is the first report of a metabolic pathway of Tetramethrin in a microorganism. Furthermore, bioaugmentation of tetramethrin-contaminated soils (50 mg·kg-1) with strain A16 (1.0 × 107 cells g-1 of soil) significantly accelerated the degradation rate of Tetramethrin, and 74.1% and 82.9% of Tetramethrin was removed from sterile and non-sterile soils within 11 days, respectively. The strain A16 was also capable of efficiently degrading a broad spectrum of synthetic pyrethroids including D-cyphenothrin, chlorempenthrin, prallethrin, and allethrin, with a degradation efficiency of 68.3%, 60.7%, 91.6%, and 94.7%, respectively, after being cultured under the same conditions for 11 days. The results of the present study confirmed the bioremediation potential of strain A16 from a contaminated environment.
A fatal case involved in pyrethroid insecticide ingestion: quantification of Tetramethrin and resmethrin in body fluids of a deceased by LC-MS/MS
Forensic Toxicol 2022 Jan;40(1):189-198.PMID:36454491DOI:10.1007/s11419-021-00594-7.
Purpose: The quantification of parent molecules of pyrethroids Tetramethrin and resmethrin in human specimens by a mass spectrometry (MS) technique has not been reported yet. A woman in her 60s was found dead in a wasteland. At the scene, an empty beer can and a spray for insecticides containing Tetramethrin and resmethrin were found. Therefore, the concentrations of Tetramethrin and resmethrin in postmortem specimens and the methanol solution used for rinsing the inside of the beer can were determined using liquid chromatography (LC)-tandem mass spectrometry (MS/MS). Methods: The quantification method by LC-MS/MS for intact parent molecules of Tetramethrin and resmethrin in whole blood and urine has been devised and validated in this work. The method was applied to the quantification of Tetramethrin and resmethrin in whole blood, urine and stomach contents obtained from a cadaver at autopsy. Results: The limits of detection of Tetramethrin and resmethrin were 0.06 and 0.03 ng/mL; limits of quantification were 0.2 and 0.1 ng/mL in blood and urine, respectively. The concentrations of Tetramethrin of the deceased were 11.1 ± 1.2 and 0.425 ± 0.017 ng/mL for stomach contents and urine, respectively; the concentration of resmethrin in stomach contents was 1.77 ± 0.18 ng/mL. The Tetramethrin and resmethrin were unstable in blood and urine at room temperature; they should be kept at not higher than 4 ℃. Conclusions: To our knowledge, this is the first report for quantification of unchanged Tetramethrin and resmethrin in human specimens obtained in a fatal case.
Systematic Stereoselectivity Evaluations of Tetramethrin Enantiomers: Stereoselective Cytotoxicity, Metabolism, and Environmental Fate in Earthworms, Soils, Vegetables, and Fruits
J Agric Food Chem 2023 Jan 11;71(1):234-243.PMID:36577083DOI:10.1021/acs.jafc.2c06489.
Tetramethrin is a widely applied type I chiral pyrethroid insecticide that exists as a mixture of four isomers. In the present study, its stereoselective cytotoxicity, bioaccumulation, degradation, and metabolism were investigated for the first time at the enantiomeric level in detail by using a sensitive chiral high-performance liquid chromatography-tandem mass spectroscopy (HPLC-MS/MS) method. Results showed that among rac-tetramethrin and its four enantiomers, the trans (+)-1R,3R-tetramethrin had the strongest inhibition effect on the PC12 cells. In the earthworm exposure trial, the concentration of trans (-)-1S,3S-tetramethrin was 0.94-8.92 times in earthworms (cultivated in natural soil) and 1.67-5.01 times (cultivated in artificial soil) higher than trans (+)-1R,3R-tetramethrin, respectively. In the greenhouse experiment, the trans (+)-1R,3R-tetramethrin and cis (+)-1R,3S-tetramethrin were preferentially degraded. Furthermore, for rat liver microsome in vitro incubation, the maximum metabolism rate of cis (-)-1S,3R-tetramethrin was 1.50 times higher than its antipodes. Altogether, the aim of this study was to provide a scientific and reasonable reference for the possibility of developing a single enantiomer to replace the application of rac-tetramethrin, which could possess better bioactivity and lower ecotoxicity, and thus permit more reliable and accurate environmental monitoring and risk assessment.
Assessment of estrogenic and androgenic activities of Tetramethrin in vitro and in vivo assays
J Toxicol Environ Health A 2005 Dec 10;68(23-24):2277-89.PMID:16326440DOI:10.1080/15287390500182453.
Tetramethrin, a synthetic pyrethroid insecticide, is used globally for agriculture, and thus potential environmental exposure to Tetramethrin is a concern. Environmental chemicals that are hormonally active (particularly estrogen or androgen) may adversely affect the reproductive and endocrine systems. However, little is known about the estrogenic and androgenic activities of Tetramethrin. In this study, uterine CaBP-9k gene expression assay and a uterotrophic assay were conducted for estrogenic activity assessment of Tetramethrin, and a Hershberger assay was conducted for androgenic activity. Estrogen receptor (ERalpha and ERbeta) protein levels were also measured in tetramethrin-treated rat uteri. Northern blot analysis showed reduction in uterine CaBP-9k mRNA levels in response to Tetramethrin, as well as when rats were given both Tetramethrin and 17beta-estradiol (E2). In the uterotrophic assay using 18-d-old female Sprague-Dawley rats, subcutaneous treatment with Tetramethrin (5 to 800 mg/kg/day) for 3 d led to a statistically significant decrease in absolute and relative uterine wet weights at all doses tested. Moreover, Tetramethrin blocked the effect of E2 on uterine weights. In addition, Tetramethrin reduced absolute and relative vaginal wet weights, and also inhibited the increases of vaginal weights produced by E2. Tetramethrin showed no androgenic on antiandrogenic activities in the Hershberger assay. These results suggest that Tetramethrin might exert endocrine-disrupting effects on female rats through antiestrogenic action.