Paraoxon

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MedKoo CAT#: 565328

CAS#: 311-45-5

Description: Paraoxon is an acetylcholinesterase inhibitor, and the active metabolite of the insecticide parathion.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-07-15. Prices are subject to change without notice.

Paraoxon is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 565328
Name: Paraoxon
CAS#: 311-45-5
Chemical Formula: C10H14NO6P
Exact Mass: 275.0559
Molecular Weight: 275.2
Elemental Analysis: C, 43.65; H, 5.13; N, 5.09; O, 34.88; P, 11.26


Synonym: Paraoxon; Phosphacol; Diethyl paraoxon; Ethyl paraoxon

IUPAC/Chemical Name: Diethyl 4-nitrophenyl phosphate

InChi Key: WYMSBXTXOHUIGT-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

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


Technical Data

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:
2934.99.9001


References

1: Houzé P, Hutin A, Lejay M, Baud FJ. Comparison of the Respiratory Toxicity and Total Cholinesterase Activities in Dimethyl Versus Diethyl Paraoxon-Poisoned Rats. Toxics. 2019 Apr 16;7(2). pii: E23. doi: 10.3390/toxics7020023. PubMed PMID: 30995784.

2: Trenque I, Magnano GC, Bolzinger MA, Roiban L, Chaput F, Pitault I, Briançon S, Devers T, Masenelli-Varlot K, Bugnet M, Amans D. Shape-selective synthesis of nanoceria for degradation of paraoxon as a chemical warfare simulant. Phys Chem Chem Phys. 2019 Mar 6;21(10):5455-5465. doi: 10.1039/c9cp00179d. PubMed PMID: 30801105.

3: Sharma G, Hu Q, Jayasinghe-Arachchige VM, Paul TJ, Schenk G, Prabhakar R. Investigating coordination flexibility of glycerophosphodiesterase (GpdQ) through interactions with mono-, di-, and triphosphoester (NPP, BNPP, GPE, and paraoxon) substrates. Phys Chem Chem Phys. 2019 Mar 6;21(10):5499-5509. doi: 10.1039/c8cp07031h. PubMed PMID: 30785142.

4: Mutharani B, Ranganathan P, Chen SM, Karuppiah C. Enzyme-free electrochemical detection of nanomolar levels of the organophosphorus pesticide paraoxon-ethyl by using a poly(N-isopropyl acrylamide)-chitosan microgel decorated with palladium nanoparticles. Mikrochim Acta. 2019 Feb 9;186(3):167. doi: 10.1007/s00604-018-3206-7. PubMed PMID: 30739232.

5: Iha HA, Kunisawa N, Shimizu S, Onishi M, Nomura Y, Matsubara N, Iwai C, Ogawa M, Hashimura M, Sato K, Kato M, Ohno Y. Mechanism Underlying Organophosphate Paraoxon-Induced Kinetic Tremor. Neurotox Res. 2019 Apr;35(3):575-583. doi: 10.1007/s12640-019-0007-7. Epub 2019 Feb 7. PubMed PMID: 30729450.

6: Alfonso M, Durán R, Fajardo D, Justo L, Faro LRF. Mechanisms of action of paraoxon, an organophosphorus pesticide, on in vivo dopamine release in conscious and freely moving rats. Neurochem Int. 2019 Mar;124:130-140. doi: 10.1016/j.neuint.2019.01.001. Epub 2019 Jan 3. PubMed PMID: 30610897.

7: Zare Z, Tehrani M, Rezaei N, Dana Ghalebarzand B, Mohammadi M. Anxiolytic activity of paraoxon is associated with alterations in rat brain glutamatergic system. Neurotoxicol Teratol. 2019 Jan - Feb;71:32-40. doi: 10.1016/j.ntt.2018.12.001. Epub 2018 Dec 19. PubMed PMID: 30576762.

8: Peng J, Yin W, Shi J, Jin X, Ni G. Magnesium and nitrogen co-doped carbon dots as fluorescent probes for quenchometric determination of paraoxon using pralidoxime as a linker. Mikrochim Acta. 2018 Dec 17;186(1):24. doi: 10.1007/s00604-018-3147-1. PubMed PMID: 30560307.

9: Wilson C, Cooper NJ, Briggs ME, Cooper AI, Adams DJ. Investigating the breakdown of the nerve agent simulant methyl paraoxon and chemical warfare agents GB and VX using nitrogen containing bases. Org Biomol Chem. 2018 Dec 5;16(47):9285-9291. doi: 10.1039/c8ob02475h. PubMed PMID: 30480295.

10: de Paula RL, de Almeida JSFD, Cavalcante SFA, Gonçalves AS, Simas ABC, Franca TCC, Valis M, Kuca K, Nepovimova E, Granjeiro JM. Molecular Modeling and In Vitro Studies of a Neutral Oxime as a Potential Reactivator for Acetylcholinesterase Inhibited by Paraoxon. Molecules. 2018 Nov 12;23(11). pii: E2954. doi: 10.3390/molecules23112954. PubMed PMID: 30424582; PubMed Central PMCID: PMC6278417.

11: Faro LRF, Fajardo D, Durán R, Alfonso M. Characterization of acute intrastriatal effects of paraoxon on in vivo dopaminergic neurotransmission using microdialysis in freely moving rats. Toxicol Lett. 2018 Dec 15;299:124-128. doi: 10.1016/j.toxlet.2018.09.017. Epub 2018 Oct 4. PubMed PMID: 30292885.

12: Morales JI, Figueroa R, Rojas M, Millán D, Tapia RA, Pavez P. Dual function of amino acid ionic liquids (Bmim[AA]) on the degradation of the organophosphorus pesticide, Paraoxon®. Org Biomol Chem. 2018 Oct 17;16(40):7446-7453. doi: 10.1039/c8ob01928b. PubMed PMID: 30264845.

13: Chagas MA, Pereira ES, Da Silva JCS, Rocha WR. Theoretical investigation of the neutral hydrolysis of diethyl 4-nitrophenyl phosphate (paraoxon) in aqueous solution. J Mol Model. 2018 Aug 29;24(9):259. doi: 10.1007/s00894-018-3798-1. PubMed PMID: 30159695.

14: González-González M, Estévez J, Del Río E, Vilanova E, Sogorb MA. Hydrolyzing activities of phenyl valerate sensitive to organophosphorus compounds paraoxon and mipafox in human neuroblastoma SH-SY5Y cells. Toxicology. 2018 Aug 1;406-407:123-128. doi: 10.1016/j.tox.2018.07.016. Epub 2018 Aug 14. PubMed PMID: 30118792.

15: Baruch Leshem A, Isaacs S, Srivastava SK, Abdulhalim I, Kushmaro A, Rapaport H. Quantitative assessment of paraoxon adsorption to amphiphilic β-sheet peptides presenting the catalytic triad of esterases. J Colloid Interface Sci. 2018 Nov 15;530:328-337. doi: 10.1016/j.jcis.2018.06.065. Epub 2018 Jun 23. PubMed PMID: 29982025.

16: Farizatto KLG, Bahr BA. Paraoxon: An Anticholinesterase That Triggers an Excitotoxic Cascade of Oxidative Stress, Adhesion Responses, and Synaptic Compromise. Eur Sci J. 2017 Oct;13:29-37. doi: 10.19044/esj.2017.c1p4. PubMed PMID: 29805717; PubMed Central PMCID: PMC5966299.

17: Baccus B, Auvin S, Dorandeu F. Electro-behavioral phenotype and cell injury following exposure to paraoxon-ethyl in mice: Effect of the genetic background. Chem Biol Interact. 2018 Jun 25;290:119-125. doi: 10.1016/j.cbi.2018.05.009. Epub 2018 May 22. PubMed PMID: 29800574.

18: Houzé P, Berthin T, Raphalen JH, Hutin A, Baud JF. High Dose of Pralidoxime Reverses Paraoxon-Induced Respiratory Toxicity in Mice. Turk J Anaesthesiol Reanim. 2018 Apr;46(2):131-138. doi: 10.5152/TJAR.2018.29660. Epub 2018 Apr 1. PubMed PMID: 29744248; PubMed Central PMCID: PMC5937459.

19: Kuca K, Jun D, Junova L, Musilek K, Hrabinova M, da Silva JAV, Ramalho TC, Valko M, Wu Q, Nepovimova E, França TCC. Synthesis, Biological Evaluation, and Docking Studies of Novel Bisquaternary Aldoxime Reactivators on Acetylcholinesterase and Butyrylcholinesterase Inhibited by Paraoxon. Molecules. 2018 May 7;23(5). pii: E1103. doi: 10.3390/molecules23051103. PubMed PMID: 29735900; PubMed Central PMCID: PMC6100540.

20: Ruggerone B, Bonelli F, Nocera I, Paltrinieri S, Giordano A, Sgorbini M. Validation of a paraoxon-based method for measurement of paraoxonase (PON-1) activity and establishment of RIs in horses. Vet Clin Pathol. 2018 Mar;47(1):69-77. doi: 10.1111/vcp.12562. PubMed PMID: 29575140.