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MedKoo Cat#: 461048 | Name: Pirimiphos-ethyl
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Description:

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

Pirimiphos-ethyl is an organophosphorous pesticide. Pirimiphos-ethyl inhibited liver kynurenine formamidase by 99%, and increased xanthurenic acid urinary excretion.

Chemical Structure

Pirimiphos-ethyl
Pirimiphos-ethyl
CAS#23505-41-1

Theoretical Analysis

MedKoo Cat#: 461048

Name: Pirimiphos-ethyl

CAS#: 23505-41-1

Chemical Formula: C13H24N3O3PS

Exact Mass: 333.1276

Molecular Weight: 333.39

Elemental Analysis: C, 46.84; H, 7.26; N, 12.60; O, 14.40; P, 9.29; S, 9.62

Price and Availability

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250mg USD 415.00 2 weeks
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Synonym
Pirimiphos-ethyl; Fernex; Primicid; PP 211; PP-211; PP211; R 42211; R-42211; R42211;
IUPAC/Chemical Name
O-(2-(diethylamino)-6-methylpyrimidin-4-yl) O,O-diethyl phosphorothioate
InChi Key
TZBPRYIIJAJUOY-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H24N3O3PS/c1-6-16(7-2)13-14-11(5)10-12(15-13)19-20(21,17-8-3)18-9-4/h10H,6-9H2,1-5H3
SMILES Code
S=P(OCC)(OC1=NC(N(CC)CC)=NC(C)=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:
Pirimiphos-ethyl is an organophosphorous pesticide.
In vitro activity:
To detect the organophosphorus (OP) pesticide pirimiphos-methyl in grain samples, a monoclonal antibody-based indirect competitive enzyme-linked immunosorbent assay (IC-ELISA) was developed and optimized. By the active esters method, pirimiphos-methyl hapten A was conjugated to keyhole limpet hemocyanin to be used as the immunogen for the production of monoclonal antibodies, and pirimiphos-methyl hapten B was conjugated to ovalbumin to be used as coating antigen. Reference: J Agric Food Chem. 2006 Jun 28;54(13):4551-6. https://pubmed.ncbi.nlm.nih.gov/16786997/
In vivo activity:
This study defined structural requirements for organophosphorous and methylcarbamate insecticides for altering the L-kynurenine pathway of L-tryptophan metabolism in mice. Pyrimidinyl phosphorothioates followed by crotonamide phosphates were the most potent compounds that changed L-tryptophan metabolism, i.e., pirimiphos-ethyl (20 mg/kg) inhibited liver kynurenine formamidase by 99%, and increased xanthurenic acid urinary excretion and plasma L-kynurenine by 576 +/- 195 and 330 +/- 44%, respectively. Reference: Eur J Pharmacol. 1993 Oct 1;248(3):237-41. https://pubmed.ncbi.nlm.nih.gov/7507440/

Preparing Stock Solutions

The following data is based on the product molecular weight 333.39 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. Yang ZY, Kolosova AY, Shim WB, Chung DH. Development of monoclonal antibodies against pirimiphos-methyl and their application to IC-ELISA. J Agric Food Chem. 2006 Jun 28;54(13):4551-6. doi: 10.1021/jf0606196. PMID: 16786997. 2. Pewnim T, Seifert J. Structural requirements for altering the L-tryptophan metabolism in mice by organophosphorous and methylcarbamate insecticides. Eur J Pharmacol. 1993 Oct 1;248(3):237-41. doi: 10.1016/0926-6917(93)90050-z. PMID: 7507440.
In vitro protocol:
1. Yang ZY, Kolosova AY, Shim WB, Chung DH. Development of monoclonal antibodies against pirimiphos-methyl and their application to IC-ELISA. J Agric Food Chem. 2006 Jun 28;54(13):4551-6. doi: 10.1021/jf0606196. PMID: 16786997.
In vivo protocol:
1. Pewnim T, Seifert J. Structural requirements for altering the L-tryptophan metabolism in mice by organophosphorous and methylcarbamate insecticides. Eur J Pharmacol. 1993 Oct 1;248(3):237-41. doi: 10.1016/0926-6917(93)90050-z. PMID: 7507440.
1: Gupta N, Singh R, Nayak SK, Das M, Jan K. Development and validation of multiresidue method for organophosphorus pesticides in lanolin using gas chromatography-tandem mass spectrometry. J Mass Spectrom. 2022 Nov;57(11):e4894. doi: 10.1002/jms.4894. PMID: 36369744. 2: Melo MG, Carqueijo A, Freitas A, Barbosa J, Silva AS. Modified QuEChERS Extraction and HPLC-MS/MS for Simultaneous Determination of 155 Pesticide Residues in Rice (Oryza sativa L.). Foods. 2019 Dec 24;9(1):18. doi: 10.3390/foods9010018. PMID: 31878165; PMCID: PMC7022397. 3: Notardonato I, Salimei E, Russo MV, Avino P. Simultaneous determination of organophosphorus pesticides and phthalates in baby food samples by ultrasound- vortex-assisted liquid-liquid microextraction and GC-IT/MS. Anal Bioanal Chem. 2018 May;410(14):3285-3296. doi: 10.1007/s00216-018-0986-x. Epub 2018 Mar 17. PMID: 29549507. 4: Dos Anjos MR, Castro IM, Souza Mde L, de Lima VV, de Aquino-Neto FR. Multiresidue method for simultaneous analysis of aflatoxin M1, avermectins, organophosphate pesticides and milbemycin in milk by ultra-performance liquid chromatography coupled to tandem mass spectrometry. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2016 Jun;33(6):995-1002. doi: 10.1080/19440049.2016.1175227. Epub 2016 May 24. PMID: 27144891. 5: Li X, Gan P, Peng R, Huang C, Yu H. Determination of 23 organophosphorous pesticides in surface water using SPME followed by GC-MS. J Chromatogr Sci. 2010 Mar;48(3):183-7. doi: 10.1093/chromsci/48.3.183. PMID: 20223083. 6: Blasco C, Font G, Picó Y. Solid-phase microextraction-liquid chromatography- mass spectrometry applied to the analysis of insecticides in honey. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2008 Jan;25(1):59-69. doi: 10.1080/02652030701424529. Epub 2007 Aug 31. PMID: 17852391. 7: Sullivan JJ, Chen YG, Goh KS. Performance assessment and validation of a paramagnetic particle-based enzyme-linked immunosorbent assay for chlorpyrifos in agricultural runoff waters. J Agric Food Chem. 2007 Aug 8;55(16):6407-16. doi: 10.1021/jf070700o. Epub 2007 Jul 6. PMID: 17616137. 8: Yang ZY, Kolosova AY, Shim WB, Chung DH. Development of monoclonal antibodies against pirimiphos-methyl and their application to IC-ELISA. J Agric Food Chem. 2006 Jun 28;54(13):4551-6. doi: 10.1021/jf0606196. PMID: 16786997. 9: Blasco C, Fernández M, Picó Y, Font G. Comparison of solid-phase microextraction and stir bar sorptive extraction for determining six organophosphorus insecticides in honey by liquid chromatography-mass spectrometry. J Chromatogr A. 2004 Mar 19;1030(1-2):77-85. doi: 10.1016/j.chroma.2003.11.037. PMID: 15043256. 10: Sullivan JJ, Goh KS. Evaluation and validation of a commercial ELISA for diazinon in surface waters. J Agric Food Chem. 2000 Sep;48(9):4071-8. doi: 10.1021/jf000432t. PMID: 10995316. 11: Lodovici M, Casalini C, Briani C, Dolara P. Oxidative liver DNA damage in rats treated with pesticide mixtures. Toxicology. 1997 Feb 14;117(1):55-60. doi: 10.1016/s0300-483x(96)03553-6. PMID: 9020199. 12: Dolara P, Torricelli F, Antonelli N. Cytogenetic effects on human lymphocytes of a mixture of fifteen pesticides commonly used in Italy. Mutat Res. 1994 Sep;325(1):47-51. doi: 10.1016/0165-7992(94)90026-4. PMID: 7521012. 13: Lodovici M, Aiolli S, Monserrat C, Dolara P, Medica A, Di Simplicio P. Effect of a mixture of 15 commonly used pesticides on DNA levels of 8-hydroxy-2-deoxyguanosine and xenobiotic metabolizing enzymes in rat liver. J Environ Pathol Toxicol Oncol. 1994;13(3):163-8. PMID: 7722883. 14: Dolara P, Vezzani A, Caderni G, Coppi C, Torricelli F. Genetic toxicity of a mixture of fifteen pesticides commonly found in the Italian diet. Cell Biol Toxicol. 1993 Oct-Dec;9(4):333-43. doi: 10.1007/BF00754461. PMID: 8039010. 15: Pewnim T, Seifert J. Structural requirements for altering the L-tryptophan metabolism in mice by organophosphorous and methylcarbamate insecticides. Eur J Pharmacol. 1993 Oct 1;248(3):237-41. doi: 10.1016/0926-6917(93)90050-z. PMID: 7507440. 16: Coetzee BB, Stanford GD, Davis DA. The resistance spectrum shown by a fenvalerate-resistant strain of blue tick (Boophilus decoloratus) to a range of ixodicides. Onderstepoort J Vet Res. 1987 Mar;54(1):79-82. PMID: 3587932. 17: Krause RT, August EM. Applicability of a carbamate insecticide multiresidue method for determining additional types of pesticides in fruits and vegetables. J Assoc Off Anal Chem. 1983 Mar;66(2):234-40. PMID: 6853408. 18: Bowman BT, Sans WW. Further water solubility determinations of insecticidal compounds. J Environ Sci Health B. 1983;18(2):221-7. doi: 10.1080/03601238309372365. PMID: 6853964. 19: Domańska I, Brzeski Z, Lewandowska-Stanek H. Ciezkie zatrucie samobójcze preparatem "Primicid 20" w przebiegu ciazy [Severe suicidal poisoning with the preparation Primicid 20 during pregnancy]. Przegl Lek. 1983;40(6):509-10. Polish. PMID: 6635237. 20: Bagness JE, Sharples WG. Determination of the substituted pyrimidine pesticides ethirimol, dimethirimol, pirimiphos-methyl, pirimiphos-ethyl and pirimicarb in technical and formulated materials by gas chromatography. Analyst. 1974 Apr;99(177):225-32. doi: 10.1039/an9749900225. PMID: 4833650.

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