MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 565328 | Name: Paraoxon
Featured

Description:

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

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

Chemical Structure

Paraoxon
Paraoxon
CAS#311-45-5

Theoretical Analysis

MedKoo Cat#: 565328

Name: Paraoxon

CAS#: 311-45-5

Chemical Formula: C10H14NO6P

Exact Mass: 275.0559

Molecular Weight: 275.20

Elemental Analysis: C, 43.65; H, 5.13; N, 5.09; O, 34.88; P, 11.26

Price and Availability

Size Price Availability Quantity
1g USD 585.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
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
Appearance
A yellow oil
Purity
>90% (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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Paraoxon is an acetylcholinesterase inhibitor.
In vitro activity:
To elucidate the mechanism of OP-induced cytotoxicity, this study examined the effects of parathion and malathion and their respective metabolites, paraoxon and malaoxon, on primary cultured human large and small airway cells. Exposure to paraoxon and malaoxon produced a dose-dependent increase in cytotoxicity following a 24-hour exposure, while treatment with parathion or malathion produced no effects at clinically relevant concentrations. Exposure to paraoxon-induced caspase activation, but malaoxon failed to induce this response. Reference: Int J Toxicol. 2015 Sep-Oct;34(5):433-41. https://pubmed.ncbi.nlm.nih.gov/26173615/
In vivo activity:
After 14 and 28 days, Bax and caspase-3 proteins were significantly increased in rats receiving 0.7 and 1 mg/kg of paraoxon. A significant decrease in Bcl-2 protein levels was also observed in 0.7 and 1 mg/kg groups after 14 days and in 1 mg/kg group after 28 days. Animals treated with 1 mg/kg of paraoxon showed a significant decrease in the number of neurons in the CA1 area. Also, those treated with 0.7 and 1 mg/kg of paraoxon showed an increase in the number of GFAP positive cells in both CA1 and CA3 areas as well as a significant decrease in survived neurons in the CA3 area. These results indicated that neuronal damage induced by convulsive doses of paraoxon in rat hippocampus is mediated in part through apoptosis mechanism. Reference: Pestic Biochem Physiol. 2020 Jun;166:104580. https://pubmed.ncbi.nlm.nih.gov/32448426/

Preparing Stock Solutions

The following data is based on the product molecular weight 275.20 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. Angelini DJ, Moyer RA, Cole S, Willis KL, Oyler J, Dorsey RM, Salem H. The Pesticide Metabolites Paraoxon and Malaoxon Induce Cellular Death by Different Mechanisms in Cultured Human Pulmonary Cells. Int J Toxicol. 2015 Sep-Oct;34(5):433-41. doi: 10.1177/1091581815593933. Epub 2015 Jul 14. PMID: 26173615. 2. Prins JM, Chao CK, Jacobson SM, Thompson CM, George KM. Oxidative stress resulting from exposure of a human salivary gland cells to paraoxon: an in vitro model for organophosphate oral exposure. Toxicol In Vitro. 2014 Aug;28(5):715-21. doi: 10.1016/j.tiv.2014.01.009. Epub 2014 Jan 29. PMID: 24486155; PMCID: PMC4048768. 3. Zare Z, Zarbakhsh S, Tehrani M, Mohammadi M. Paraoxon-induced damage in rat hippocampus is associated with alterations in the expression of apoptosis-related proteins. Pestic Biochem Physiol. 2020 Jun;166:104580. doi: 10.1016/j.pestbp.2020.104580. Epub 2020 Apr 8. PMID: 32448426. 4. 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. PMID: 30610897.
In vitro protocol:
1. Angelini DJ, Moyer RA, Cole S, Willis KL, Oyler J, Dorsey RM, Salem H. The Pesticide Metabolites Paraoxon and Malaoxon Induce Cellular Death by Different Mechanisms in Cultured Human Pulmonary Cells. Int J Toxicol. 2015 Sep-Oct;34(5):433-41. doi: 10.1177/1091581815593933. Epub 2015 Jul 14. PMID: 26173615. 2. Prins JM, Chao CK, Jacobson SM, Thompson CM, George KM. Oxidative stress resulting from exposure of a human salivary gland cells to paraoxon: an in vitro model for organophosphate oral exposure. Toxicol In Vitro. 2014 Aug;28(5):715-21. doi: 10.1016/j.tiv.2014.01.009. Epub 2014 Jan 29. PMID: 24486155; PMCID: PMC4048768.
In vivo protocol:
1. Zare Z, Zarbakhsh S, Tehrani M, Mohammadi M. Paraoxon-induced damage in rat hippocampus is associated with alterations in the expression of apoptosis-related proteins. Pestic Biochem Physiol. 2020 Jun;166:104580. doi: 10.1016/j.pestbp.2020.104580. Epub 2020 Apr 8. PMID: 32448426. 2. 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. PMID: 30610897.
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.