Chemistry:Paraoxon
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.[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]
EA-1370 is a phosphonate analogue, isopropyl para-nitrophenyl methylphosphonate, the junction of the nerve agent sarin with the leaving group of paraoxon.[4] Contact with the fluoride ion in a polar-aprotic solvent regenerates it to sarin.[5][6]
See also
- Armine (chemical)
- O-isobutylarmine
- O-neopentyl p-nitrophenyl methylphosphonate
References
- ↑ "Development of status epilepticus, sustained calcium elevations and neuronal injury in a rat survival model of lethal paraoxon intoxication". Neurotoxicology 44: 17–26. September 2014. doi:10.1016/j.neuro.2014.04.006. PMID 24785379. Bibcode: 2014NeuTx..44...17D.
- ↑ "Chronic behavioral and cognitive deficits in a rat survival model of paraoxon toxicity". Neurotoxicology 44: 352–7. September 2014. doi:10.1016/j.neuro.2014.08.008. PMID 25172410. Bibcode: 2014NeuTx..44..352D.
- ↑ "Paraoxon". NTI Country Overviews: South Africa: Chemical Capabilities. Washington, DC: Nuclear Threat Initiative. March 2004. http://www.nti.org/e_research/profiles/SAfrica/Chemical/2440_3598.html.
- ↑ Molecular Catalysis and Interactions in Aqueous Solutions. (Report). 24 March 1964. Contract No. DA 18-108-AMC-88A - Final Report.. https://apps.dtic.mil/sti/tr/pdf/AD0437607.pdf.
- ↑ "Solvent effects on displacement of fluoride ion from isopropyl methylphosphonofluoridate". Journal of the American Chemical Society 93 (17): 4093–4103. 1971-08-01. doi:10.1021/ja00746a001. ISSN 0002-7863. Bibcode: 1971JAChS..93.4093D.
- ↑ "Toxicity of isopropyl parathion. Effect of structure on toxicity and anticholinesterase activity". Journal of Agricultural and Food Chemistry 17 (2): 243–248. March 1969. doi:10.1021/jf60162a038. Bibcode: 1969JAFC...17..243C.
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