Cyclosarin
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| 1: 1 mixture of ( R ) -form (left) and ( S ) -form (right) | ||||||||||
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| Surname | Cyclosarin | |||||||||
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| Molecular formula | C 7 H 14 FO 2 P | |||||||||
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| Molar mass | 180.16 g mol −1 | |||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
Cyclosarin ( CmpF , GF ) is a toxic chemical compound from the group of phosphonic acid - ester , their effect on the inhibition of acetylcholinesterase is based. The compound was developed with the aim of being used as a chemical warfare agent or as a nerve agent. Cyclosarin is structurally similar to sarin , whereby - as a difference to sarin - the isopropyl group has been replaced by a cyclohexyl group.
Cyclosarin is a slightly volatile compound that is practically insoluble in water. It is chemically very stable and only hydrolyzes when exposed to heat or in the presence of nucleophilic reagents. Cyclosarin is one of the strongest cholinesterase inhibitors (pI50 = 10.1); the toxicity, however, when administered subcutaneously to mice and rats is about two to six times less than that of sarin.
Cyclosarin was synthesized in 1949 by Gerhard Schrader's team , who had previously been the first to synthesize tabun and sarin.
It was stored by the Iraqi army in connection with sarin as a chemical warfare agent. It is less volatile than sarin and therefore more advantageous in the hot climatic conditions there. Another reason may have been that, unlike sarin precursors, it was not embargoed. According to J. Tucker, the manufacture is similar to sarin, except that isopropyl alcohol is replaced with cyclohexanol , which was readily available from the Iraqi oil industry. Rocket cargoes and supplies of around 8.5 tons of sarin and cyclosarin were released by US forces in March Destroyed by demolition in Khamisyah in 1991. US Army personnel were also exposed to low doses, which later gave rise to speculation that cyclosarin might have been one of the triggers of the Gulf War syndrome.
structure
Cyclosarin has a stereocenter on the phosphorus atom, so there are two enantiomers , one has an ( R ) configuration, the other has an ( S ) configuration. The usual production processes produce a racemic cyclosarin, that is to say a 1: 1 mixture of the ( R ) -methylfluorophosphonic acid isocyclohexyl ester and the ( S ) -methyl fluorophosphonic acid isocyclohexyl ester.
See also
Individual evidence
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ a b c Entry on cyclosarin in the ChemIDplus database of the United States National Library of Medicine (NLM)
- ^ Science Journal . Vol. 3 (4), p. 33, 1967.
- ↑ Canadian Journal of Physiology and Pharmacology . Vol. 44, pp. 745, 1966.
- ^ Entry on sarin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.
- ↑ Spradling, Dillman: The molecular toxicology of chemical warfare agents , in James Fishbein (Ed.), Advances in Molecular Toxicology, Volume 5, Elsevier 2011, p. 112.
- ↑ a b J. Tucker, War of Nerves, Pantheon 2006, p. 271.
- ↑ K. Willis, H. Salem, FR Siddell, Article Cyclosarin, in Encyclopedia of Toxicology, 2014, pp. 726-730.
- ↑ Ramesh Gupta (ed.), Handbook of Toxicology of Chemical Warfare Agents, Elsevier, 2015, p. 3.50