Paraoxon

Paraoxon
Clinical data
ATC code	S01EB10 (WHO) ;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name Diethyl 4-nitrophenyl phosphate;
CAS Number	311-45-5 ;
PubChem CID	9395;
ChemSpider	9026 ;
UNII	Q9CX8P80JW;
KEGG	D10529 ;
ChEBI	CHEBI:27827 ;
ChEMBL	ChEMBL23838 ;
CompTox Dashboard (EPA)	DTXSID6024046 ;
ECHA InfoCard	100.005.657
Chemical and physical data
Formula	C10H14NO6P
Molar mass	275.197 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-][N+](=O)c1ccc(OP(=O)(OCC)OCC)cc1;
	InChI 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 ; Key:WYMSBXTXOHUIGT-UHFFFAOYSA-N ;
	(what is this?)

Paraoxon is a parasympathomimetic 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.^[1]^[2] 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.^[3]

References[]

^ Deshpande LS, Carter DS, Phillips KF, Blair RE, DeLorenzo RJ (September 2014). "Development of status epilepticus, sustained calcium elevations and neuronal injury in a rat survival model of lethal paraoxon intoxication". Neurotoxicology. 44: 17–26. doi:10.1016/j.neuro.2014.04.006. PMC 4176600. PMID 24785379.
^ Deshpande LS, Phillips K, Huang B, DeLorenzo RJ (September 2014). "Chronic behavioral and cognitive deficits in a rat survival model of paraoxon toxicity". Neurotoxicology. 44: 352–7. doi:10.1016/j.neuro.2014.08.008. PMC 4175062. PMID 25172410.
^ NTI Country Overviews:South Africa:Chemical Capabilities:Paraoxon Archived 2008-07-08 at the Wayback Machine

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[1] Deshpande LS, Carter DS, Phillips KF, Blair RE, DeLorenzo RJ (September 2014). "Development of status epilepticus, sustained calcium elevations and neuronal injury in a rat survival model of lethal paraoxon intoxication". Neurotoxicology. 44: 17–26. doi:10.1016/j.neuro.2014.04.006. PMC 4176600. PMID 24785379.

[2] Deshpande LS, Phillips K, Huang B, DeLorenzo RJ (September 2014). "Chronic behavioral and cognitive deficits in a rat survival model of paraoxon toxicity". Neurotoxicology. 44: 352–7. doi:10.1016/j.neuro.2014.08.008. PMC 4175062. PMID 25172410.

[3] NTI Country Overviews:South Africa:Chemical Capabilities:Paraoxon Archived 2008-07-08 at the Wayback Machine

[1]

[2]

[3]

v t Pest control: Insecticides
Carbamates	Aldicarb Aminocarb Bendiocarb Butocarboxim Carbaryl Carbofuran Carbosulfan m-Cumenyl methylcarbamate Ethienocarb Fenobucarb Methomyl Metolcarb Oxamyl Promecarb Propoxur
Inorganic compounds	Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Cryolite Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green
Insect growth regulators	Benzoylureas Diflubenzuron Flufenoxuron Hydroprene Lufenuron Methoprene Pyriproxyfen
Neonicotinoids	Acetamiprid Clothianidin Dinotefuran Imidacloprid Nitenpyram Nithiazine Thiacloprid Thiamethoxam
Organochlorides	Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT DFDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene
Organophosphorus	Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Coumaphos Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Dimefox Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Isoxathion Malathion Methamidophos Methidathion Mevinphos Mipafox Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos R-16661 Schradan Temefos Tebupirimfos Terbufos Tetrachlorvinphos Trichlorfon
Pyrethroids	Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Fluvalinate Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin
Ryanoids	Chlorantraniliprole Cyantraniliprole Flubendiamide Ryanodine
Other chemicals	Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner (+milbemycin oxime) Pyriprole Sarolaner Sesamex Spinosad Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone
Metabolites	Oxon Malaoxon Paraoxon TCPy
Biopesticides	Bacillus thuringiensis Baculovirus Beauveria bassiana Isaria fumosorosea Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paenibacillus popilliae Purpureocillium lilacinum

Clinical data


ATC code	S01EB10 (WHO)
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name Diethyl 4-nitrophenyl phosphate
CAS Number	311-45-5^Y
PubChem CID	9395
ChemSpider	9026^Y
UNII	Q9CX8P80JW
KEGG	D10529^N
ChEBI	CHEBI:27827^N
ChEMBL	ChEMBL23838^Y
CompTox Dashboard (EPA)	DTXSID6024046
ECHA InfoCard	100.005.657
Chemical and physical data
Formula	C₁₀H₁₄NO₆P
Molar mass	275.197 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [O-][N+](=O)c1ccc(OP(=O)(OCC)OCC)cc1
InChI 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^Y Key:WYMSBXTXOHUIGT-UHFFFAOYSA-N^Y
^NY (what is this?)

Paraoxon

See also[]

References[]