Thiosarin

For thiosarin, unlike sarin, the literature contains little information.Augerson, W. S. Review of the Scientific Literature as it Pertains to Gulf War Illnesses. Volume 5. Chemical and Biological Warfare Agents. p 200 It is reported as a colorless liquid with a characteristic organosulfur odor when pure. It is estimated to have a boiling point of 144-167 °C. It is a more nonpolar compound, with a solubility in water of 7 g/L. Thiosarin probably belongs to the IVA compound series, leaving it much less volatile than sarin. It has a greater persistence in the environment than sarin.

Absorption frequencies of sarin derivatives showed that the frequency of stretching of the P-F and P=S bond of thiosarin is lower than that of its oxygenated analogue.{{Cite book |last=Theodorus. |first=Kuiper, Antonius Emilius |url=http://worldcat.org/oclc/634367125 |title=Adsorption and decomposition of sarin on gamma-alumina |date=1974 |oclc=634367125}}

Its toxicity was discovered in the 1970s by Friedrick Wilhelm Hoffmann and Ray King Irino. They were responsible for synthesizing and analyzing a series of sulfur G-agent compounds.Hoffmann et al. US 4,012,465 The open literature reports that the compound has been cataloged as GS, but this statement is incorrect, it belongs to EA-1246. GS agents are a series of G compounds. GBS is generally lower than sarin. The little open military literature may be due to the low toxicity of this series of compounds.

The possibility of a chemical warfare agent candidate was raised when Bogomazov and his colleagues discovered that thiosarin had the ability to break through military gas mask filters, where it would then be converted to its analogue.{{Cite book |last=S. |first=Mirzayanov, Vil |url=http://worldcat.org/oclc/299069417 |title=State secrets : an insider's chronicle of the Russian chemical weapons program |date=2009 |publisher=Outskirts Press, Inc |isbn=978-1-4327-2566-2 |oclc=299069417}}{{rp|115}} An investigation by Vil Mirzayanov refuted these results.{{rp|118}}

Thiosarin is used as a precursor to sarin.

The preparation route is quite similar to that of sarin. The synthesis routes of thiosarin are manifold.{{Cite book |first=Robert |last=Turkington |url=http://worldcat.org/oclc/489624232 |title=Chemicals used for illegal purposes : a guide for first responders to identify explosives, recreational drugs, and poisons |date=2010 |publisher=Wiley |isbn=978-0-470-18780-7 |oclc=489624232|page=319}}

Regardless of the synthesis route chosen, the final reaction is usually the reaction of isopropyl methylthiophosphonochloridate with fluorides.

Thiosarin has a tendency to convert to the all oxygen analogue by divers mechanisms..Senkbeil et al. US 3,337,658 In anhydrous medium, thiosarin is oxidized to form GB.{{Cite journal |last=Davidson |first=R.Stephen |last2=Walker |first2=Martin D. |last3=Bhardwaj |first3=Raj K. |date=1987 |title=The oxidative desulphurisation and deselenation at pentacovalent phosphorus catalysed by metalloporphyrins |url=https://doi.org/10.1016/S0040-4039(00)96262-2 |journal=Tetrahedron Letters |volume=28 |issue=26 |pages=2981–2984 |doi=10.1016/s0040-4039(00)96262-2 |issn=0040-4039|url-access=subscription }}

File:Degradation of GBS.png

In the controlated aqueous medium, without the presence of oxygen, the tendency is to evolve hydrogen sulfide.

File:GBS hydrolysis.png

Along with the discovery of the high toxicity of this series of compounds, Hoffmann discovered that the S-alkyl isomers, unlike the alkyl alkylphosphonothiol compounds, were less toxic than the G(S) agents.

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Category:Nerve agents

Category:G-series nerve agents

Category:Acetylcholinesterase inhibitors

Category:Isopropyl esters

Category:Methylphosphonofluoridates

Category:Sulfur compounds