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Methyl Parathion

(Synonyms: 甲基对硫磷) 目录号 : GC47660

An organophosphate insecticide

Methyl Parathion Chemical Structure

Cas No.:298-00-0

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产品描述

Methyl parathion is an organophosphate insecticide.1 It is converted into an oxon-containing metabolite in vivo, similar to other organophosphate pesticides, that inhibits acetylcholinesterase. Methyl parathion is lethal to lab strains and field isolates of tobacco budworm larvae (LD50s = 7 and 81.8-128.3 μg/g, respectively).2 It reduces the number of stink bugs (C. sayi) caught per 100 net sweeps when applied to alfalfa fields at a concentration of 0.4 pounds per acre.3 Methyl parathion increases sister chromatid exchange (SCE) in a concentration-dependent manner and induces cell cycle arrest at the M1 phase in V79 cells at a concentration of 40 μg/ml.4 It is toxic to rats (LD50 = 14 mg/kg).1

1.Guo, J.-X., Wu, J.J.-Q., Wight, J.B., et al.Mechanistic insight into acetylcholinesterase inhibition and acute toxicity of organophosphorus compounds: A molecular modeling studyChem. Res. Toxicol.19(2)209-216(2006) 2.Martinez-Carrillo, J.L., and Reynolds, H.T.Dosage-mortality studies with pyrethroids and other insecticides on the tobacco budworm (Lepidoptera: Noctuidae) from the Imperial Valley, CaliforniaJ. Econ. Entomol.76(5)983-986(1983) 3.Reynolds, H.T., Stern, V.M., Fukoto, T.R., et al.Potential use of dylox and other insecticides in a control program for field crop pests in CaliforniaJ. Econ. Entomol.53(1)72-78(1960) 4.Chen, H.H., Hsueh, J.L., Sirianni, S.R., et al.Induction of sister-chromatid exchanges and cell cycle delay in cultured mammalian cells treated with eight organophosphorus pesticidesMutat. Res.88(3)307-316(1981)

Chemical Properties

Cas No. 298-00-0 SDF
别名 甲基对硫磷
Canonical SMILES COP(OC1=CC=C([N+]([O-])=O)C=C1)(OC)=S
分子式 C8H10NO5PS 分子量 263.2
溶解度 Chloroform: Slightly Soluble,Methanol: Slightly Soluble 储存条件 Store at -20°C
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1 mM 3.7994 mL 18.997 mL 37.9939 mL
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Research Update

Methyl Parathion: a review of health effects

J Toxicol Environ Health B Crit Rev 2003 Mar-Apr;6(2):185-210.PMID:12554434DOI:10.1080/10937400306471.

Methyl Parathion is an organophosphorus (OP) insecticide with insecticidal properties derived from acetylcholinesterase (AChE) inhibition; this same property is also the root of its toxicity in humans. Poisoning with Methyl Parathion leads to cholinergic overstimulation with signs of toxicity including sweating, dizziness, vomiting, diarrhea, convulsions, cardiac arrest, respiratory arrest, and, in extreme cases, death. Reports of Methyl Parathion intoxication, usually seen only in field pesticide applicators, have increased throughout the United States as a result of unauthorized application of Methyl Parathion inside homes. The health concerns of the use of Methyl Parathion have resulted in cancellation of its use in most food crops in the United States. This review examines the well-documented neurotoxicity of Methyl Parathion as well as effects on other organ systems.

Methyl Parathion: an organophosphate insecticide not quite forgotten

Rev Environ Health 2006 Jan-Mar;21(1):57-67.PMID:16700430DOI:10.1515/reveh.2006.21.1.57.

Methyl Parathion (MP), a toxic organophosphate insecticide approved for outdoor use only, is classified by the World Health Organization (WHO) as a Category Ia (extremely toxic) and by the United States Environmental Protection Agency (U.S. EPA) as a Toxicity Category I (most toxic) insecticide. In several U.S. states in the late 1980s and early 1990s, toxic exposures were created by the illegal use of MP indoors by uncertified pest control operators. As the health effects of MP exposure became evident with increasing public awareness, intervention by the U.S. government, in collaboration with several agencies and public initiatives, led to investigations of MP exposure. After evidence of MP metabolites from urine samples confirmed the exposure, in 1998 the indoor use of MP was banned in the U.S. to protect human health, especially that of children, and the environment. Toxic exposures to MP also occurred in developing countries. In El Salvador, occupational exposure to MP in farmers introduced environmental exposures among agricultural families, who presented with the cholinergic features of MP toxicity. Suicidal MP poisoning was reported in Nepal. A fatal accidental poisoning in children in Peru reflected the serious health risk of pesticides in developing countries. The negligence of pesticide exporters raised human rights issues over the tragedy. Nevertheless, MP exposure remains a potential health risk in both the U.S. and the developing world. Preventive measures in reducing the use of toxic chemicals should be taken seriously to protect human health and the environment.

Electrochemical detection of Methyl Parathion using calix[6]arene/bismuth ferrite/multiwall carbon nanotube-modified fluorine-doped tin oxide electrode

Mikrochim Acta 2022 Nov 23;189(12):461.PMID:36416997DOI:10.1007/s00604-022-05562-5.

A highly sensitive electrochemical sensor using a calix[6]arene/bismuth ferrite/multiwall carbon nanotube-modified fluorine-doped tin oxide electrode (CA6/BFO/MWCNTs/FTO) was fabricated for the detection of Methyl Parathion. The MWCNTs, BFO, and CA6 were consecutively cast onto the FTO electrode surface to enhance the surface area, electron transfer, and selectivity of sensors. The electrochemical behavior of CA6/BFO/MWCNTs/FTO was studied via cyclic voltammetry and electrochemical impedance spectroscopy. MP was detected via cyclic voltammetry in a phosphate buffer solution at pH 7.0. The working principle of the sensor involves a linear decrease in the anodic peak current of BFO with increasing MP concentration. The linear working ranges are 0.005-0.05 nM and 0.07-1.5 nM. The CA6/BFO/MWCNTs/FTO sensor provides a low detection limit (S/N = 3) of 5 pM and a high electrochemical sensitivity of 1.23 A μM-1 cm-2. The fabricated sensor was successfully applied to assess the presence and amount of MP in vegetables and fruits (recoveries of 82.0-106.8%), with results comparable to high-performance liquid chromatography.

Proteomic analysis of Burkholderia zhejiangensis CEIB S4-3 during the Methyl Parathion degradation process

Pestic Biochem Physiol 2022 Oct;187:105197.PMID:36127069DOI:10.1016/j.pestbp.2022.105197.

Methyl Parathion is an organophosphorus pesticide widely employed worldwide to control pests in agricultural and domestic environments. However, due to its intensive use, high toxicity, and environmental persistence, Methyl Parathion is recognized as an important ecosystem and human health threat, causing severe environmental pollution events and numerous human poisoning and deaths each year. Therefore, identifying and characterizing microorganisms capable of fully degrading Methyl Parathion and its degradation metabolites is a crucial environmental task for the bioremediation of pesticide-polluted sites. Burkholderia zhejiangensis CEIB S4-3 is a bacterial strain isolated from agricultural soils capable of immediately hydrolyzing Methyl Parathion at a concentration of 50 mg/L and degrading the 100% of the released p-nitrophenol in a 12-hour lapse when cultured in minimal salt medium. In this study, a comparative proteomic analysis was conducted in the presence and absence of Methyl Parathion to evaluate the biological mechanisms implicated in the Methyl Parathion biodegradation and resistance by the strain B. zhejiangensis CEIB S4-3. In each treatment, the changes in the protein expression patterns were evaluated at three sampling times, zero, three, and nine hours through the use of two-dimensional polyacrylamide gel electrophoresis (2D-PAGE), and the differentially expressed proteins were identified by mass spectrometry (MALDI-TOF). The proteomic analysis allowed the identification of 72 proteins with differential expression, 35 proteins in the absence of the pesticide, and 37 proteins in the experimental condition in the presence of Methyl Parathion. The identified proteins are involved in different metabolic processes such as the carbohydrate and amino acids metabolism, carbon metabolism and energy production, fatty acids β-oxidation, and the aromatic compounds catabolism, including enzymes of the both p-nitrophenol degradation pathways (Hydroquinone dioxygenase and Hydroxyquinol 1,2 dioxygenase), as well as the overexpression of proteins implicated in cellular damage defense mechanisms such as the response and protection of the oxidative stress, reactive oxygen species defense, detoxification of xenobiotics, and DNA repair processes. According to these data, B. zhejiangensis CEIB S4-3 overexpress different proteins related to aromatic compounds catabolism and with the p-nitrophenol degradation pathways, the higher expression levels observed in the two subunits of the enzyme Hydroquinone dioxygenase, suggest a preferential use of the Hydroquinone metabolic pathway in the p-nitrophenol degradation process. Moreover the overexpression of several proteins implicated in the oxidative stress response, xenobiotics detoxification, and DNA damage repair reveals the mechanisms employed by B. zhejiangensis CEIB S4-3 to counteract the adverse effects caused by the Methyl Parathion and p-nitrophenol exposure.

Study of detoxification of Methyl Parathion by dielectric barrier discharge (DBD) non-thermal plasma at gas-liquid interface:mechanism and bio-toxicity evaluation

Chemosphere 2022 Nov;307(Pt 1):135620.PMID:35839991DOI:10.1016/j.chemosphere.2022.135620.

Methyl Parathion (MP) as an organophosphorus pesticide has been used in the control of agricultural pests and diseases. Due to its high toxicity and persistence in the environment, MP may pose threat to human health when it is released into environmental water. For MP treatment, people have found that oxidative degradation of MP may generate some intermediates which are more toxic than MP itself, such as methyl paraoxon. Herein, we proposed a new method of applying dielectric barrier discharge (DBD) non-thermal plasma technology to treat MP in aqueous solution, and investigated the influences of different gases, pH value, discharge voltage/power, and main active species on the MP removal efficiency. In particular, the safety of DBD treatment was concerned with analysis of the biological toxicity of the byproducts from the DBD oxidation, and the DBD-induced degradation together with the involved mechanism was explored therein. The results showed that the production of toxic intermediates could be effectively suppressed or avoided under certain treatment conditions. As such, this work demonstrates that the proper application of DBD plasma technology with necessary caution can detoxify Methyl Parathion effectively, and also provides a practical guide for low-temperature plasma application in treatment of various organophosphorus pesticides in agricultural wastewater.