Quinalphos | CAS#13593-03-8 | pesticide

MedKoo Cat#: 461752 | Name: Quinalphos

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Quinalphos is an organic thiophosphate and an organothiophosphate insecticide.

Chemical Structure

Quinalphos

CAS#13593-03-8

Theoretical Analysis

MedKoo Cat#: 461752

Name: Quinalphos

CAS#: 13593-03-8

Chemical Formula: C12H15N2O3PS

Exact Mass: 298.0541

Molecular Weight: 298.30

Elemental Analysis: C, 48.32; H, 5.07; N, 9.39; O, 16.09; P, 10.38; S, 10.75

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 750.00	2 Weeks

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Synonym

Quinalphos; Chinalphos; Diethquinalphion; Ekalux; Quinaltaf; S-6538; S 6538; S6538; Savall;

IUPAC/Chemical Name

O,O-diethyl O-(quinoxalin-2-yl) phosphorothioate

InChi Key

JYQUHIFYBATCCY-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H15N2O3PS/c1-3-15-18(19,16-4-2)17-12-9-13-10-7-5-6-8-11(10)14-12/h5-9H,3-4H2,1-2H3

SMILES Code

S=P(OCC)(OC1=NC2=CC=CC=C2N=C1)OCC

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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Quinalphos is an EC 3.1.1. (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.

In vitro activity:

Quinalphos is known to induce various toxic effects in nontarget species and experimental animals. In this study, the tumorigenic potential of Quinalphos was evaluated following topical exposure in Swiss albino mice. Long-term animal bioassays revealed that Quinalphos has only tumour-initiating potential at a dose of 10 mg/kg body weight. Quinalphos exposure failed to produce neoplasia when tested for complete carcinogenic activity at all three tested dose levels or tumour promoting activity. Reference: Cancer Lett. 2000 Jan 1;148(1):1-7. https://pubmed.ncbi.nlm.nih.gov/10680586/

In vivo activity:

The effect of quinalphos on blood esterases was investigated in male buffalo calves. Quinalphos markedly inactivated serum carboxylesterase (69-90%) and plasma cholinesterase activity (75-88%). The results suggest that quinalphos is an effective inhibitor of blood esterases in vivo and its repeated exposure to buffaloes may impair detoxification of organophosphorus insecticides that are mainly biodegraded by carboxylesterase enzyme. Reference: Toxicol Lett. 1983 Oct-Nov;19(1-2):165-9. https://pubmed.ncbi.nlm.nih.gov/6658822/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 298.30 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.

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. Mishra V, Srivastava N. Organophosphate pesticides-induced changes in the redox status of rat tissues and protective effects of antioxidant vitamins. Environ Toxicol. 2015 Apr;30(4):472-82. doi: 10.1002/tox.21924. Epub 2013 Nov 18. PMID: 24248738. 2. Shukla Y, Singh A, Mehrotra NK. Evaluation of carcinogenic and co-carcinogenic potential Quinalphos in mouse skin. Cancer Lett. 2000 Jan 1;148(1):1-7. doi: 10.1016/s0304-3835(99)00228-1. PMID: 10680586. 3. Eddleston M, Clutton RE, Taylor M, Thompson A, Worek F, John H, Thiermann H, Scott C. Efficacy of an organophosphorus hydrolase enzyme (OpdA) in human serum and minipig models of organophosphorus insecticide poisoning. Clin Toxicol (Phila). 2020 May;58(5):397-405. doi: 10.1080/15563650.2019.1655149. Epub 2019 Aug 27. PMID: 31452424; PMCID: PMC7114914. 4. Srivastava AK, Paul BS, Malik JK. Effect of repeated oral administration of quinalphos on blood esterases in Bubalus bubalis. Toxicol Lett. 1983 Oct-Nov;19(1-2):165-9. doi: 10.1016/0378-4274(83)90278-3. PMID: 6658822.

In vitro protocol:

In vivo protocol:

1. Eddleston M, Clutton RE, Taylor M, Thompson A, Worek F, John H, Thiermann H, Scott C. Efficacy of an organophosphorus hydrolase enzyme (OpdA) in human serum and minipig models of organophosphorus insecticide poisoning. Clin Toxicol (Phila). 2020 May;58(5):397-405. doi: 10.1080/15563650.2019.1655149. Epub 2019 Aug 27. PMID: 31452424; PMCID: PMC7114914. 2. Srivastava AK, Paul BS, Malik JK. Effect of repeated oral administration of quinalphos on blood esterases in Bubalus bubalis. Toxicol Lett. 1983 Oct-Nov;19(1-2):165-9. doi: 10.1016/0378-4274(83)90278-3. PMID: 6658822.

1: Zhang Q, Wang F, Haq IU, Li C, Gou Y, Zhang K, Liu H, Liu C. Comparative toxicity and enzymatic detoxification responses in Spodoptera frugiperda (Lepidoptera: Noctuidae) to two insecticides. Ecotoxicol Environ Saf. 2024 Aug 24;284:116917. doi: 10.1016/j.ecoenv.2024.116917. Epub ahead of print. PMID: 39182280. 2: Jain R, Singh MK, Ali N, Khan MR, Bajaj A, Mudiam MKR. Innovative disposable in-tip cellulose paper (DICP) device for facile determination of pesticides in postmortem blood samples: A proof-of-concept study. J Chromatogr B Analyt Technol Biomed Life Sci. 2024 Sep 15;1245:124268. doi: 10.1016/j.jchromb.2024.124268. Epub 2024 Aug 5. PMID: 39126993. 3: Singh S, Thakur J, Katna S, Devi N, Brar GS, Singh G. Dissipation behaviour and dietary risk evaluation of pesticides on cucumber. Environ Monit Assess. 2024 Aug 5;196(9):783. doi: 10.1007/s10661-024-12926-2. PMID: 39098866. 4: Mahajan MR, Patil PO. Designed fluorescence "on-off-on" probe based on cobalt, zinc, and nitrogen co-doped graphene quantum dots: A case of quinalphos sensing. Luminescence. 2024 Jul;39(7):e4835. doi: 10.1002/bio.4835. PMID: 39049704. 5: Mishra S, Budania Y, Tyagi A, Pratap Singh S, Kumar P, Singh S. Copper Oxide Anchored Carbon Nanofibers: A Versatile Platform for Multiplex Detection of Antibiotics, Heavy Metals and Pesticides. Chem Asian J. 2024 May 17;19(10):e202400241. doi: 10.1002/asia.202400241. Epub 2024 Mar 29. PMID: 38441388. 6: Tanveer S, Ilyas N, Akhtar N, Akhtar N, Bostan N, Hasnain Z, Niaz A, Zengin G, Gafur A, Fitriatin BN. Unlocking the interaction of organophosphorus pesticide residues with ecosystem: Toxicity and bioremediation. Environ Res. 2024 May 15;249:118291. doi: 10.1016/j.envres.2024.118291. Epub 2024 Feb 1. PMID: 38301757. 7: Xie T, Huang J, Wu J, Zhang Q. Evaluation of supercritical fluid chromatography coupled to tandem mass spectrometry for the analysis of pesticide residues in grain. J Sep Sci. 2024 Jan;47(1):e2300623. doi: 10.1002/jssc.202300623. Epub 2023 Dec 8. PMID: 38066396. 8: Li JD, Shen X, Xu ZL, Liang YF, Shen YD, Yang JY, Wang H. Molecular Evolution of Antiparathion Nanobody with Enhanced Sensitivity and Specificity Based on Structural Analysis. J Agric Food Chem. 2023 Oct 11;71(40):14758-14768. doi: 10.1021/acs.jafc.3c05176. Epub 2023 Sep 28. PMID: 37768036. 9: Liang YF, Li JD, Fang RY, Xu ZL, Luo L, Chen ZJ, Yang JY, Shen YD, Ueda H, Hammock B, Wang H. Design of an Antigen-Triggered Nanobody-Based Fluorescence Probe for PET Immunoassay to Detect Quinalphos in Food Samples. Anal Chem. 2023 Aug 22;95(33):12321-12328. doi: 10.1021/acs.analchem.3c01696. Epub 2023 Aug 1. PMID: 37527540. 10: Li JD, Wu GP, Li LH, Wang LT, Liang YF, Fang RY, Zhang QL, Xie LL, Shen X, Shen YD, Xu ZL, Wang H, Hammock BD. Structural Insights into the Stability and Recognition Mechanism of the Antiquinalphos Nanobody for the Detection of Quinalphos in Foods. Anal Chem. 2023 Aug 1;95(30):11306-11315. doi: 10.1021/acs.analchem.3c01370. Epub 2023 Jul 10. PMID: 37428097; PMCID: PMC10829938. 11: Zhang Z, Meng M, Wu Q, Kim JH, Zhu Y. Biodegradation and metabolic pathway of quinalphos by Cunninghamella elegans ATCC36112. Biotechnol Lett. 2023 Jul;45(7):873-883. doi: 10.1007/s10529-023-03393-9. Epub 2023 May 17. PMID: 37195489. 12: Hu W, Li Z, Ou H, Wang X, Wang Q, Tao Z, Huang S, Huang Y, Wang G, Pan X. Novosphingobium album sp. nov., Novosphingobium organovorum sp. nov. and Novosphingobium mangrovi sp. nov. with the organophosphorus pesticides degrading ability isolated from mangrove sediments. Int J Syst Evol Microbiol. 2023 Apr;73(4). doi: 10.1099/ijsem.0.005843. PMID: 37115596. 13: Ganaie MI, Jan I, Mayer AN, Dar AA, Mayer IA, Ahmed P, Sofi JA. Health Risk Assessment of Pesticide Residues in Drinking Water of Upper Jhelum Region in Kashmir Valley-India by GC-MS/MS. Int J Anal Chem. 2023 Jan 27;2023:6802782. doi: 10.1155/2023/6802782. PMID: 36741419; PMCID: PMC9897932. 14: Sujeeth NK, Aravinth R, Thandeeswaran M, Angayarkanni J, Rajasekar A, Mythili R, Gnanadesigan M. Toxicity analysis and biomarker response of Quinalphos Organophosphate Insecticide (QOI) on eco-friendly exotic Eudrilus eugeniae earthworm. Environ Monit Assess. 2023 Jan 6;195(2):274. doi: 10.1007/s10661-022-10834-x. PMID: 36607436. 15: Bhattacharyya S, Poi R, Sen MB, Hazra DK, Mandal S, Karmakar R. Long-term profound investigation of Fenoxaprop-p-ethyl and indirect pesticide pollution in jute-cropped environmental ecosystem for dietary and ecological risk assessment. Environ Geochem Health. 2023 Jun;45(6):3683-3698. doi: 10.1007/s10653-022-01432-4. Epub 2022 Dec 7. PMID: 36478235. 16: Indira M, Chowallur MJ, M K A, Lin CY, Chang SS, Sooraj M, Thomas J. Effect of pesticide ban on suicide trend - a 20-year study from a tertiary care center in Central Kerala from 2001 to 2020. Clin Toxicol (Phila). 2022 Nov;60(11):1214-1219. doi: 10.1080/15563650.2022.2129671. Epub 2022 Oct 20. PMID: 36263906. 17: Zaki MSA, El-Kott AF, AlGwaiz HIM, Sideeg AM, Andarawi M, Eid RA. The effectiveness of vitamin C on quinalphos ileal toxicity: a study of histological, ultrastructural, and oxidative stress markers. Environ Sci Pollut Res Int. 2022 Aug;29(38):57896-57904. doi: 10.1007/s11356-022-19820-9. Epub 2022 Mar 31. PMID: 35359206. 18: Ssemugabo C, Guwatudde D, Ssempebwa JC, Bradman A. Pesticide Residue Trends in Fruits and Vegetables from Farm to Fork in Kampala Metropolitan Area, Uganda-A Mixed Methods Study. Int J Environ Res Public Health. 2022 Jan 26;19(3):1350. doi: 10.3390/ijerph19031350. PMID: 35162373; PMCID: PMC8835516. 19: Shati AA, Zaki MSA, Alqahtani YA, Haidara MA, Al-Shraim M, Dawood AF, Eid RA. Potential Protective Effect of Vitamin C on Qunalphos-Induced Cardiac Toxicity: Histological and Tissue Biomarker Assay. Biomedicines. 2021 Dec 24;10(1):39. doi: 10.3390/biomedicines10010039. PMID: 35052719; PMCID: PMC8772816. 20: Talari K, Ganji SK, Kommu M, Tiruveedula RR, Upadhyayula V. Quantitative determination of targeted and untargeted pesticide residues in coconut milk by liquid chromatography - Atmospheric pressure chemical ionization - high energy collisional dissociation tandem high-resolution mass spectrometry. J Chromatogr A. 2021 Dec 6;1659:462649. doi: 10.1016/j.chroma.2021.462649. Epub 2021 Oct 29. PMID: 34742133.