Structure via PubChem · Public domain (PubChem)
paraoxon
Sign in to saveAlso known as O,O-diethyl O-p-nitrophenyl phosphate, p-nitrophenyl diethyl phosphate, ethyl paraoxon, diethyl paraoxon, phosphacol, diethyl p-nitrophenyl phosphate, phosphoric acid diethyl 4-nitrophenyl ester
Paraoxon is a parasympathomimetic drug which acts as an cholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an ophthalmological drug against glaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. Paraoxon has been used by scientists to study acute and chronic effects of organophosphate intoxication. It is easily absorbed th
In the Vinony graph
Within Vinony's link graph, paraoxon is referenced by 599 other articles, and connects out to botulinum toxin group, carbamate and chlorpyrifos.
Vinony files it under 4-Nitrophenyl compounds, Acetylcholinesterase inhibitors and Chemical pages without DrugBank identifier.
Its subject is documented across 13 Wikipedia language editions.
Chemical data
- Formula
- C10H14NO6P
- Molecular weight
- 275.19 g/mol
- IUPAC name
- diethyl (4-nitrophenyl) phosphate
- SMILES
- CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+](=O)[O-]
- InChIKey
- WYMSBXTXOHUIGT-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 90.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
- Indications
- glaucoma
via ChEMBL · EBI
Research
2,891 papers- Mechanism Underlying Organophosphate Paraoxon-Induced Kinetic Tremor.Neurotoxicity research · 2019
- Apoptosis is involved in paraoxon-induced histological changes in rat cerebellum.Drug and chemical toxicology · 2022
- Enhancing Paraoxon Binding to Organophosphorus Hydrolase Active Site.International journal of molecular sciences · 2021
- Enzymatic decontamination of paraoxon-ethyl limits long-term effects in planarians.Scientific reports · 2020
- Combined Pre- and Posttreatment of Paraoxon Exposure.Molecules (Basel, Switzerland) · 2020
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 275.056
- Has use
- insecticide
Show 4 more facts
- chemical formula
- C₁₀H₁₄NO₆P
- canonical SMILES
- CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+](=O)[O-]
- Commons category
- Paraoxon
- subject has role
- acetylcholinesterase inhibitor
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Paraoxon is a parasympathomimetic drug which acts as an cholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an ophthalmological drug against glaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. Paraoxon has been used by scientists to study acute and chronic effects of organophosphate intoxication. It is easily absorbed through skin, and was allegedly used as an assassination weapon by the apartheid-era South African chemical weapons program Project Coast.
EA-1370 is a phosphonate analogue, isopropyl para-nitrophenyl methylphosphonate, the junction of the nerve agent sarin with the leaving group of paraoxon. Contact with the fluoride ion in a polar-aprotic solvent regenerates it to sarin.
Excerpted from Wikipedia’s “paraoxon” article, available under the CC BY-SA 4.0 licence.