Parathion
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MedKoo CAT#: 571292

CAS#: 56-38-2

Description: Parathion is a highly toxic cholinesterase inhibitor that is used as an acaricide and as an insecticide.

Chemical Structure

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Parathion
CAS# 56-38-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 571292
Name: Parathion
CAS#: 56-38-2
Chemical Formula: C10H14NO5PS
Exact Mass: 291.03
Molecular Weight: 291.258
Elemental Analysis: C, 41.24; H, 4.85; N, 4.81; O, 27.47; P, 10.63; S, 11.01

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100mg USD 190
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Synonym: Parathion; Aphamite; Corothion; Murfos ; NSC 8933; NSC-8933; NSC8933

IUPAC/Chemical Name: O,O-diethyl O-(4-nitrophenyl) phosphorothioate

InChi Key: LCCNCVORNKJIRZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

SMILES Code: S=P(OCC)(OCC)OC1=CC=C([N+]([O-])=O)C=C1

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

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: Parathion is a highly toxic cholinesterase inhibitor.
In vitro activity: The goal of this study was to investigate the in vitro effects of mPT (methyl parathion) on cells in the oral cavity and evaluate the potential protective role of epigallocathechin-3-gallate (EGCG) on these effects. Human gingival fibroblasts (HGF) were exposed to 10, 50, or 100 μ g/ml mPT for 24 h and assessed for oxidative stress, as evidenced by reactive generation of oxygen species (ROS), induction of apoptotic cell death, DNA damage (comet assay and cytochinesis-block micronucleus test), and nitric oxide (NO) production. The results showed that mPT produced significant oxidative stress, cytotoxicity, and genotoxicity and increased NO levels through stimulation of inducible NO synthase expression. Reference: J Toxicol Environ Health A. 2015;78(19):1227-40. https://pubmed.ncbi.nlm.nih.gov/26479333/
In vivo activity: The results showed that MP (methyl parathion) exposure reduced spontaneous movement, hatching, and survival rates of zebrafish embryos and induced developmental abnormalities such as shortened body length, yolk edema, and spinal curvature. Notably, MP was found to induce cardiac abnormalities, including pericardial edema and decreased heart rate. Exposure to MP resulted in the accumulation of reactive oxygen species (ROS), decreased superoxide dismutase (SOD) activity, increased catalase (CAT) activity, elevated malondialdehyde (MDA) levels, and caused cardiac apoptosis in zebrafish embryos. Moreover, MP affected the transcription of cardiac development-related genes (vmhc, sox9b, nppa, tnnt2, bmp2b, bmp4) and apoptosis-related genes (p53, bax, bcl2). Reference: Toxics. 2023 Jan 15;11(1):84. https://pubmed.ncbi.nlm.nih.gov/36668810/

Preparing Stock Solutions

The following data is based on the product molecular weight 291.26 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. Argentin G, Divizia M, Cicchetti R. Oxidative Stress, Cytotoxicity, and Genotoxicity Induced by Methyl Parathion in Human Gingival Fibroblasts: Protective Role of Epigallocatechin-3-Gallate. J Toxicol Environ Health A. 2015;78(19):1227-40. doi: 10.1080/15287394.2015.1079582. Epub 2015 Oct 19. PMID: 26479333. 2. Edwards FL, Yedjou CG, Tchounwou PB. Involvement of oxidative stress in methyl parathion and parathion-induced toxicity and genotoxicity to human liver carcinoma (HepG₂) cells. Environ Toxicol. 2013 Jun;28(6):342-8. doi: 10.1002/tox.20725. Epub 2011 May 4. PMID: 21544925; PMCID: PMC3768275. 3. Chen T, Chen H, Wang A, Yao W, Xu Z, Wang B, Wang J, Wu Y. Methyl Parathion Exposure Induces Development Toxicity and Cardiotoxicity in Zebrafish Embryos. Toxics. 2023 Jan 15;11(1):84. doi: 10.3390/toxics11010084. PMID: 36668810; PMCID: PMC9866970. 4. Urióstegui-Acosta M, Tello-Mora P, Solís-Heredia MJ, Ortega-Olvera JM, Piña-Guzmán B, Martín-Tapia D, González-Mariscal L, Quintanilla-Vega B. Methyl parathion causes genetic damage in sperm and disrupts the permeability of the blood-testis barrier by an oxidant mechanism in mice. Toxicology. 2020 May 30;438:152463. doi: 10.1016/j.tox.2020.152463. Epub 2020 Apr 12. PMID: 32294493.
In vitro protocol: 1. Argentin G, Divizia M, Cicchetti R. Oxidative Stress, Cytotoxicity, and Genotoxicity Induced by Methyl Parathion in Human Gingival Fibroblasts: Protective Role of Epigallocatechin-3-Gallate. J Toxicol Environ Health A. 2015;78(19):1227-40. doi: 10.1080/15287394.2015.1079582. Epub 2015 Oct 19. PMID: 26479333. 2. Edwards FL, Yedjou CG, Tchounwou PB. Involvement of oxidative stress in methyl parathion and parathion-induced toxicity and genotoxicity to human liver carcinoma (HepG₂) cells. Environ Toxicol. 2013 Jun;28(6):342-8. doi: 10.1002/tox.20725. Epub 2011 May 4. PMID: 21544925; PMCID: PMC3768275.
In vivo protocol: 1. Chen T, Chen H, Wang A, Yao W, Xu Z, Wang B, Wang J, Wu Y. Methyl Parathion Exposure Induces Development Toxicity and Cardiotoxicity in Zebrafish Embryos. Toxics. 2023 Jan 15;11(1):84. doi: 10.3390/toxics11010084. PMID: 36668810; PMCID: PMC9866970. 2. Urióstegui-Acosta M, Tello-Mora P, Solís-Heredia MJ, Ortega-Olvera JM, Piña-Guzmán B, Martín-Tapia D, González-Mariscal L, Quintanilla-Vega B. Methyl parathion causes genetic damage in sperm and disrupts the permeability of the blood-testis barrier by an oxidant mechanism in mice. Toxicology. 2020 May 30;438:152463. doi: 10.1016/j.tox.2020.152463. Epub 2020 Apr 12. PMID: 32294493.

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1: Shi H, Sheng E, Feng L, Zhou L, Hua X, Wang M. Simultaneous detection of imidacloprid and parathion by the dual-labeled time-resolved fluoroimmunoassay. Environ Sci Pollut Res Int. 2015 Oct;22(19):14882-90. doi: 10.1007/s11356-015-4697-y. Epub 2015 May 22. PubMed PMID: 25994268.

2: Tabassum N, Rafique U, Balkhair KS, Ashraf MA. Chemodynamics of methyl parathion and ethyl parathion: adsorption models for sustainable agriculture. Biomed Res Int. 2014;2014:831989. doi: 10.1155/2014/831989. Epub 2014 Feb 6. PubMed PMID: 24689059; PubMed Central PMCID: PMC3932840.

3: Liu G, Guo W, Yin Z. Covalent fabrication of methyl parathion hydrolase on gold nanoparticles modified carbon substrates for designing a methyl parathion biosensor. Biosens Bioelectron. 2014 Mar 15;53:440-6. doi: 10.1016/j.bios.2013.10.025. Epub 2013 Oct 24. PubMed PMID: 24211455.

4: Jan YH, Richardson JR, Baker AA, Mishin V, Heck DE, Laskin DL, Laskin JD. Novel approaches to mitigating parathion toxicity: targeting cytochrome P450-mediated metabolism with menadione. Ann N Y Acad Sci. 2016 Aug;1378(1):80-86. doi: 10.1111/nyas.13156. Epub 2016 Jul 21. Review. PubMed PMID: 27441453; PubMed Central PMCID: PMC5220671.

5: Halaimi FZ, Kellali Y, Couderchet M, Semsari S. Comparison of biosorption and phytoremediation of cadmium and methyl parathion, a case-study with live Lemna gibba and Lemna gibba powder. Ecotoxicol Environ Saf. 2014 Jul;105:112-20. doi: 10.1016/j.ecoenv.2014.02.002. Epub 2014 May 7. Review. PubMed PMID: 24815048.

6: Liao X, Zhang C, Liu Y, Luo Y, Wu S, Yuan S, Zhu Z. Abiotic degradation of methyl parathion by manganese dioxide: Kinetics and transformation pathway. Chemosphere. 2016 May;150:90-96. doi: 10.1016/j.chemosphere.2016.02.028. Epub 2016 Feb 16. PubMed PMID: 26891361.

7: Edwards FL, Yedjou CG, Tchounwou PB. Involvement of oxidative stress in methyl parathion and parathion-induced toxicity and genotoxicity to human liver carcinoma (HepG₂) cells. Environ Toxicol. 2013 Jun;28(6):342-8. doi: 10.1002/tox.20725. Epub 2011 May 4. PubMed PMID: 21544925; PubMed Central PMCID: PMC3768275.

8: Valdes SA, Vieira LG, Ferreira CH, dos Santos Mendonça J, Ribeiro PR, de Abreu Fernandes E, Santos AL. Effects of Exposure to Methyl Parathion on Egg Hatchability and Eggshell Chemical Composition in Podocnemis expansa (Testudines, Podocnemididae). Zoolog Sci. 2015 Apr;32(2):135-40. doi: 10.2108/zs140164. PubMed PMID: 25826061.

9: Xu S, Guo C, Li Y, Yu Z, Wei C, Tang Y. Methyl parathion imprinted polymer nanoshell coated on the magnetic nanocore for selective recognition and fast adsorption and separation in soils. J Hazard Mater. 2014 Jan 15;264:34-41. doi: 10.1016/j.jhazmat.2013.10.060. Epub 2013 Nov 2. PubMed PMID: 24275470.

10: Tan L, Li W, Li H, Tang Y. Development of surface imprinted core-shell nanoparticles and their application in a solid-phase dispersion extraction matrix for methyl parathion. J Chromatogr A. 2014 Apr 4;1336:59-66. doi: 10.1016/j.chroma.2014.02.011. Epub 2014 Feb 8. PubMed PMID: 24576608.

11: Gerent GG, Spinelli A. Environmentally-friendly in situ plated bismuth-film electrode for the quantification of the endocrine disruptor parathion in skimmed milk. J Hazard Mater. 2016 May 5;308:157-63. doi: 10.1016/j.jhazmat.2016.01.038. Epub 2016 Jan 16. PubMed PMID: 26812083.

12: Zhao Y, Zhang W, Lin Y, Du D. The vital function of Fe3O4@Au nanocomposites for hydrolase biosensor design and its application in detection of methyl parathion. Nanoscale. 2013 Feb 7;5(3):1121-6. doi: 10.1039/c2nr33107a. Epub 2013 Jan 2. PubMed PMID: 23280070.

13: Ben Salem I, Fekih S, Sghaier H, Bousselmi M, Saidi M, Landoulsi A, Fattouch S. Effect of ionising radiation on polyphenolic content and antioxidant potential of parathion-treated sage (Salvia officinalis) leaves. Food Chem. 2013 Nov 15;141(2):1398-405. doi: 10.1016/j.foodchem.2013.04.008. Epub 2013 Apr 18. PubMed PMID: 23790930.

14: Ibrahim R, Kasting GB. Partitioning and diffusion of parathion in human dermis. Int J Pharm. 2012 Oct 1;435(1):33-7. doi: 10.1016/j.ijpharm.2012.03.023. Epub 2012 Mar 29. PubMed PMID: 22484178.

15: Patnaik R, Padhy RN. Evaluation of geno-toxicity of methyl parathion and chlorpyrifos to human liver carcinoma cell line (HepG2). Environ Sci Pollut Res Int. 2016 May;23(9):8492-9. doi: 10.1007/s11356-015-5963-8. Epub 2016 Jan 19. PubMed PMID: 26782680.

16: Foxenberg RJ, Ellison CA, Knaak JB, Ma C, Olson JR. Cytochrome P450-specific human PBPK/PD models for the organophosphorus pesticides: chlorpyrifos and parathion. Toxicology. 2011 Jul 11;285(1-2):57-66. doi: 10.1016/j.tox.2011.04.002. Epub 2011 Apr 13. PubMed PMID: 21514354.

17: Anh DH, Cheunrungsikul K, Wichitwechkarn J, Surareungchai W. A colorimetric assay for determination of methyl parathion using recombinant methyl parathion hydrolase. Biotechnol J. 2011 May;6(5):565-71. doi: 10.1002/biot.201000348. Epub 2011 Mar 7. PubMed PMID: 21381204.

18: Kumar J, D'Souza SF. Microbial biosensor for detection of methyl parathion using screen printed carbon electrode and cyclic voltammetry. Biosens Bioelectron. 2011 Jul 15;26(11):4289-93. doi: 10.1016/j.bios.2011.04.027. Epub 2011 Apr 22. PubMed PMID: 21605969.

19: Pino NJ, Dominguez MC, Penuela GA. Isolation of a selected microbial consortium capable of degrading methyl parathion and p-nitrophenol from a contaminated soil site. J Environ Sci Health B. 2011;46(2):173-80. doi: 10.1080/03601234.2011.539142. PubMed PMID: 21328125.

20: Yao JJ, Gao NY, Deng Y, Ma Y, Li HJ, Xu B, Li L. Sonolytic degradation of parathion and the formation of byproducts. Ultrason Sonochem. 2010 Jun;17(5):802-9. doi: 10.1016/j.ultsonch.2010.01.016. Epub 2010 Feb 4. PubMed PMID: 20303819.