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Chemical Compound Review

AGN-PC-0CVO1P     dihydroxy-methyl- sulfanylidene-phosphorane

Synonyms: CHEMBL122577, CHEBI:301983, LS-107106, AKOS006277926, BRN 2345158, ...
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Disease relevance of dihydroxy-methyl-thioxo-phosphorane

  • An enzyme termed organophosphorus hydrolase (OPH), derived from Pseudomonas diminuta, had been found previously to hydrolyze the powerful acetylcholinesterase (AChE) inhibitor O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothiolate (VX) [1].
  • Cardiac toxicity of methylphosphonothiolate (MPT), an organophosphorus compound, has been investigated in the rat [2].

High impact information on dihydroxy-methyl-thioxo-phosphorane

  • For the alkaline hydrolysis of O,S-dimethyl methylphosphonothiolate, it was found that the P-O and P-S bond cleavage processes are kinetically competitive but that the products of P-S bond cleavage are thermodynamically favored [3].
  • [reaction: see text] Potential energy surfaces for the alkaline hydrolysis of sarin and O,S-dimethyl methylphosphonothiolate, a VX model compound, and the perhydrolysis of the latter have been computed at the MP2/6-31+G(d)//mPW1K/MIDI! level of theory [3].
  • Contrary to commonly used pesticides, the rate of volatilization of extremely toxic chemicals such as the nerve agent O-ethyl S-2-(N,N-diisopropylamino)ethyl methylphosphonothiolate (VX) cannot be readily obtained under environmental conditions due to its high mammalian toxicity that would require extraordinary precautions [4].
  • Methanol chemical ionization quadrupole ion trap mass spectrometry of O-ethyl S-[2-(diisopropylamino)ethyl] methylphosphonothiolate (VX) and its degradation products [5].
  • A microinstillation technique of inhalation exposure was utilized to assess lung injury following chemical warfare nerve agent VX [methylphosphonothioic acid S-(2-[bis(1-methylethyl)amino]ethyl) O-ethyl ester] exposure in guinea pigs [6].

Associations of dihydroxy-methyl-thioxo-phosphorane with other chemical compounds


Analytical, diagnostic and therapeutic context of dihydroxy-methyl-thioxo-phosphorane


  1. Hydrolysis of tetriso by an enzyme derived from Pseudomonas diminuta as a model for the detoxication of O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothiolate (VX). Hoskin, F.C., Walker, J.E., Dettbarn, W.D., Wild, J.R. Biochem. Pharmacol. (1995) [Pubmed]
  2. Cardiac abnormalities in rats treated with methylphosphonothiolate. Robineau, P. Toxicol. Appl. Pharmacol. (1987) [Pubmed]
  3. Ab initio molecular orbital and density functional studies on the solvolysis of sarin and O,S-dimethyl methylphosphonothiolate, a VX-like compound. Seckute, J., Menke, J.L., Emnett, R.J., Patterson, E.V., Cramer, C.J. J. Org. Chem. (2005) [Pubmed]
  4. Laboratory setup for long-term monitoring of the volatilization of hazardous materials: preliminary tests of O-ethyl S-2-(N,N-diisopropylamino)ethyl methylphosphonothiolate on asphalt. Waysbort, D., Manisterski, E., Leader, H., Manisterski, B., Ashani, Y. Environ. Sci. Technol. (2004) [Pubmed]
  5. Methanol chemical ionization quadrupole ion trap mass spectrometry of O-ethyl S-[2-(diisopropylamino)ethyl] methylphosphonothiolate (VX) and its degradation products. Rohrbaugh, D.K. Journal of chromatography. A. (2000) [Pubmed]
  6. Acute Lung Injury Following Inhalation Exposure to Nerve Agent VX in Guinea Pigs. Wright, B.S., Rezk, P.E., Graham, J.R., Steele, K.E., Gordon, R.K., Sciuto, A.M., Nambiar, M.P. Inhalation toxicology. (2006) [Pubmed]
  7. Analysis of methylphosphonic acid, ethyl methylphosphonic acid and isopropyl methylphosphonic acid at low microgram per liter levels in groundwater. Sega, G.A., Tomkins, B.A., Griest, W.H. Journal of chromatography. A. (1997) [Pubmed]
  8. Analysis of VX on soil particles using ion trap secondary ion mass spectrometry. Groenewold, G.S., Appelhans, A.D., Gresham, G.L., Olson, J.E., Jeffery, M., Wright, J.B. Anal. Chem. (1999) [Pubmed]
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