Phosphamidon | CAS#13171-21-6 | organophosphate cholinesterase inhibitor

MedKoo Cat#: 592905 | Name: Phosphamidon

Description:

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

Phosphamidon is a polar compound and organophosphate cholinesterase inhibitor that is used as an insecticide and pesticide.

Chemical Structure

Phosphamidon

CAS#13171-21-6

Theoretical Analysis

MedKoo Cat#: 592905

Name: Phosphamidon

CAS#: 13171-21-6

Chemical Formula: C10H19ClNO5P

Exact Mass: 299.0689

Molecular Weight: 299.69

Elemental Analysis: C, 40.08; H, 6.39; Cl, 11.83; N, 4.67; O, 26.69; P, 10.34

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Synonym

Phosphamidon

IUPAC/Chemical Name

Phosphoric acid, 2-chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester

InChi Key

RGCLLPNLLBQHPF-HJWRWDBZSA-N

InChi Code

InChI=1S/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3/b9-8-

SMILES Code

O=P(OC)(OC)O/C(C)=C(Cl)/C(N(CC)CC)=O

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Phosphamidon is an organophosphate cholinesterase inhibitor that is used as an insecticide.

In vitro activity:

Human peripheral blood mononuclear cells (PBMC) were incubated with increasing concentrations of phosphamidon (0-20 μM) for 6-24 h. The MTT assay reveals that phosphamidon induces cytotoxicity in a dose-dependent manner. DNA fragmentation assay revealed that at low concentration of phosphamidon (1 μM), no appreciable change in DNA fragmentation was seen; however, distinct fragmentation was observed beyond 2.5 μM. Phosphamidon was found to cause significant depletion of GSH, which correlates well with the percentage of cells undergoing apoptosis. Reference: J Biochem Mol Toxicol. 2010 Sep-Oct;24(5):286-92. https://pubmed.ncbi.nlm.nih.gov/20979154/

In vivo activity:

The present study enumerates the ameliorating effect of ginger extract (GE) against phosphamidon (PHO, an organophosphorus insecticide) induced hepatotoxicity. GE was prepared from dried ginger and characterized for compound profile and antioxidant activity. Eight groups of albino rats (n = 6) were treated with 1/5th lethal dose of PHO (phosphamidon) for 5-20 days. Out of the treated 8 groups, 4 were simultaneously fed with GE (1 mg/kg body wt.) along with PHO. Reference: Indian J Exp Biol. 2015 Sep;53(9):574-84. https://pubmed.ncbi.nlm.nih.gov/26548077/

Preparing Stock Solutions

The following data is based on the product molecular weight 299.69 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. Ahmed T, Tripathi AK, Ahmed RS, Banerjee BD. Assessment of phosphamidon-induced apoptosis in human peripheral blood mononuclear cells: protective effects of N-acetylcysteine and curcumin. J Biochem Mol Toxicol. 2010 Sep-Oct;24(5):286-92. doi: 10.1002/jbt.20337. PMID: 20979154. 2. Sreekumaran Nair R, Paulmurugan R, Singh AJ. Simple radioactive assay for the estimation of DNA breaks. J Appl Toxicol. 2002 Jan-Feb;22(1):19-23. doi: 10.1002/jat.807. PMID: 11807925. 3. Mukherjee S, Mukherjee N, Saini P, Roy P, Babu SP. Ginger extract ameliorates phosphamidon induced hepatotoxicity. Indian J Exp Biol. 2015 Sep;53(9):574-84. PMID: 26548077. 4. Suke SG, Shukla A, Mundhada D, Banerjee BD, Mediratta PK. Effect of phosphamidon on cognition and oxidative stress and its modulation by ascorbic acid and 4'-chlorodiazepam in rats. Pharmacol Biochem Behav. 2013 Jan;103(3):637-42. doi: 10.1016/j.pbb.2012.10.015. Epub 2012 Nov 2. PMID: 23128021.

In vitro protocol:

In vivo protocol:

1. Mukherjee S, Mukherjee N, Saini P, Roy P, Babu SP. Ginger extract ameliorates phosphamidon induced hepatotoxicity. Indian J Exp Biol. 2015 Sep;53(9):574-84. PMID: 26548077. 2. Suke SG, Shukla A, Mundhada D, Banerjee BD, Mediratta PK. Effect of phosphamidon on cognition and oxidative stress and its modulation by ascorbic acid and 4'-chlorodiazepam in rats. Pharmacol Biochem Behav. 2013 Jan;103(3):637-42. doi: 10.1016/j.pbb.2012.10.015. Epub 2012 Nov 2. PMID: 23128021.

1: Drakopoulou SK, Kokolakis SE, Karagiannidis AL, Dasenaki ME, Maragou NC, Thomaidis NS. A comprehensive HRMS methodology using LC-(ESI)-/GC-(APCI)-QTOF MS complementary platforms for wide-scope target screening of >750 pesticides in olive oil. Anal Methods. 2024 May 3;16(17):2684-2692. doi: 10.1039/d4ay00181h. PMID: 38623768. 2: Heartz S, MacLean DA, Johns RC, Carleton D, Amos-Binks L, Anderson Q, Yu Y, Lewis AD, Lavigne D, Burant JB, Edge CB. Historical pesticide applications for the treatment of eastern spruce budworm infestations in New Brunswick. Ecology. 2023 Jul;104(7):e4068. doi: 10.1002/ecy.4068. Epub 2023 May 29. PMID: 37248722. 3: Mardani Z, Shakoori A, Peiravian F, Nouri L, Salamzadeh J. Development of A Liquid Chromatography-Mass Spectrometry Technique for Evaluation of Multi-class Pesticides in Rice Samples. Iran J Pharm Res. 2021 Winter;20(1):165-174. doi: 10.22037/ijpr.2020.113071.14095. PMID: 34400950; PMCID: PMC8170775. 4: Li H, Chang Q, Bai R, Lv X, Cao T, Shen S, Liang S, Pang G. Simultaneous determination and risk assessment of highly toxic pesticides in the market-sold vegetables and fruits in China: A 4-year investigational study. Ecotoxicol Environ Saf. 2021 Sep 15;221:112428. doi: 10.1016/j.ecoenv.2021.112428. Epub 2021 Jun 17. PMID: 34146981. 5: Markus A, Gbadamosi AO, Yusuff AS, Agi A, Oseh J. Magnetite- sporopollenin/graphene oxide as new preconcentration adsorbent for removal of polar organophosphorus pesticides in vegetables. Environ Sci Pollut Res Int. 2018 Dec;25(35):35130-35142. doi: 10.1007/s11356-018-3402-3. Epub 2018 Oct 16. PMID: 30328041. 6: Zhou Q, Li J, Wang B, Wang S, Li H, Chen J. Selectivity improvement of positive photoionization ion mobility spectrometry for rapid detection of organophosphorus pesticides by switching dopant concentration. Talanta. 2018 Jan 1;176:247-252. doi: 10.1016/j.talanta.2017.08.045. Epub 2017 Aug 13. PMID: 28917748. 7: Rashidi Nodeh H, Wan Ibrahim WA, Kamboh MA, Sanagi MM. New magnetic graphene- based inorganic-organic sol-gel hybrid nanocomposite for simultaneous analysis of polar and non-polar organophosphorus pesticides from water samples using solid-phase extraction. Chemosphere. 2017 Jan;166:21-30. doi: 10.1016/j.chemosphere.2016.09.054. Epub 2016 Sep 25. PMID: 27681257. 8: Kim S, Park MY, Kim HJ, Shin JY, Ko KY, Kim DG, Kim M, Kang HG, So B, Park SW. Analysis of Insecticides in Dead Wild Birds in Korea from 2010 to 2013. Bull Environ Contam Toxicol. 2016 Jan;96(1):25-30. doi: 10.1007/s00128-015-1688-0. Epub 2015 Nov 16. PMID: 26573839. 9: Mukherjee S, Mukherjee N, Saini P, Roy P, Babu SP. Ginger extract ameliorates phosphamidon induced hepatotoxicity. Indian J Exp Biol. 2015 Sep;53(9):574-84. PMID: 26548077. 10: Cho HR, Park JS, Kim J, Han SB, Choi YS. Multiresidue method for the quantitation of 20 pesticides in aquatic products. Anal Bioanal Chem. 2015 Dec;407(30):9043-52. doi: 10.1007/s00216-015-9071-x. Epub 2015 Oct 14. PMID: 26466578. 11: Alizadeh A, Talebi-Jahromi K, Hosseininaveh V, Ghadamyari M. Toxicological and biochemical characterizations of AChE in phosalone-susceptible and resistant populations of the common pistachio psyllid, Agonoscena pistaciae. J Insect Sci. 2014 Feb 5;14:18. doi: 10.1093/jis/14.1.18. PMID: 25373165; PMCID: PMC4199533. 12: Shakouri A, Yazdanpanah H, Shojaee MH, Kobarfard F. Method Development for Simultaneous Determination of 41 Pesticides in Rice Using LC-MS/MS Technique and Its Application for the Analysis of 60 Rice Samples Collected from Tehran Market. Iran J Pharm Res. 2014 Summer;13(3):927-35. PMID: 25276193; PMCID: PMC4177653. 13: Ko KY, Shin JY, Kim DG, Kim M, Son SW. Determination of organophosphorus pesticides in stomach contents of postmortem animals by QuEChERS and gas chromatography. J Anal Toxicol. 2014 Nov-Dec;38(9):667-71. doi: 10.1093/jat/bku097. Epub 2014 Aug 16. PMID: 25129879. 14: Chowdhury MA, Jahan I, Karim N, Alam MK, Abdur Rahman M, Moniruzzaman M, Gan SH, Fakhruddin AN. Determination of carbamate and organophosphorus pesticides in vegetable samples and the efficiency of gamma-radiation in their removal. Biomed Res Int. 2014;2014:145159. doi: 10.1155/2014/145159. Epub 2014 Mar 10. PMID: 24711991; PMCID: PMC3966332. 15: Hazarika R. Neurotoxic impact of organophosphate pesticide phosphomedon on the albino rat. J Environ Biol. 2014 Mar;35(2):427-30. PMID: 24665773. 16: Tang Q, Wang X, Yu F, Qiao X, Xu Z. Simultaneous determination of ten organophosphate pesticide residues in fruits by gas chromatography coupled with magnetic separation. J Sep Sci. 2014 Apr;37(7):820-7. doi: 10.1002/jssc.201301161. Epub 2014 Feb 27. PMID: 24470377. 17: Binici B, Yenisoy-Karakaş S, Bilsel M, Durmaz-Hilmioğlu N. Sources of polycyclic hydrocarbons and pesticides in soluble fraction of deposition samples in Kocaeli, Turkey. Environ Sci Pollut Res Int. 2014 Feb;21(4):2907-17. doi: 10.1007/s11356-013-2239-z. Epub 2013 Oct 24. PMID: 24154853. 18: Wang X, Qiao X, Ma Y, Zhao T, Xu Z. Simultaneous determination of nine trace organophosphorous pesticide residues in fruit samples using molecularly imprinted matrix solid-phase dispersion followed by gas chromatography. J Agric Food Chem. 2013 Apr 24;61(16):3821-7. doi: 10.1021/jf400269q. Epub 2013 Apr 12. PMID: 23544352. 19: Xin J, Qiao X, Ma Y, Xu Z. Simultaneous separation and determination of eight organophosphorous pesticide residues in vegetables through molecularly imprinted solid-phase extraction coupled to gas chromatography. J Sep Sci. 2012 Dec;35(24):3501-8. doi: 10.1002/jssc.201200754. PMID: 23225716. 20: Suke SG, Shukla A, Mundhada D, Banerjee BD, Mediratta PK. Effect of phosphamidon on cognition and oxidative stress and its modulation by ascorbic acid and 4'-chlorodiazepam in rats. Pharmacol Biochem Behav. 2013 Jan;103(3):637-42. doi: 10.1016/j.pbb.2012.10.015. Epub 2012 Nov 2. PMID: 23128021.