Cyclosarin 801463 221394658 2008-06-24T09:31:36Z Mendaliv 200402 Undoing own edit (using [[WP:HG|Huggle]]) {{Distinguish|Cycloserine}} {| border="1" cellspacing="0" cellpadding="2" align="right" |+'''Cyclosarin''' |- | align="center" bgcolor="#FFFFFF" colspan="2" | [[Image:Cyclosarin-2D-skeletal.png|140px|Skeletal formula of cyclosarin]] [[Image:Cyclosarin-3D-balls.png|140px|Ball-and-stick of cyclosarin]] |- ! bgcolor="#FFDEAD" colspan="2" | Discovery |- ! align="left" | <small>Discovered by</small> |<small>[[Gerhard Schrader|Dr. Gerhard Schrader]]</small> |- ! align="left" | <small>Discovered in</small> | <small>[[1949]]</small> |- ! bgcolor="#FFDEAD" colspan="2" | Chemical Characteristics |- ! align="left" | <small>[[IUPAC|Chemical Name]]</small> | <small>(fluoro-methyl-phosphoryl)oxycyclohexane</small> |- ! align="left" | <small>Chemical Family</small> |<small>Fluorinated organophosphorous compound</small> |- ! align="left" | <small>[[Chemical Formula]]</small> | <small>C<sub>7</sub>H<sub>14</sub>FO<sub>2</sub>P</small> |- ! align="left" | <small>Airborne Exposure Limit</small> | 0.0001 mg/m<sup>3</sup> |- ! align="left" | <small>[[Boiling point]]</small> | <small>239 °C (462 °F)</small> |- ! align="left" | <small>[[Freezing point|Freezing/Melting point]]</small> | <small>-30 °C (-22 °F)</small> |- ! align="left" | <small>[[Vapor pressure]]</small> | <small><!--0.044 of some units or another --> at 25 °C</small> |- ! align="left" | <small>[[Flash point]]</small> | <small>94 °C (201 °F)</small> |- ! align="left" | <small>Vapor [[relative density]] (air=1)</small> | <small>6.2</small> |- ! align="left" | <small>Liquid [[density]]</small> | <small>1.1278 g/cc @ 25 °C</small> |- ! align="left" | <small>[[Solubility]] in Water</small> | <small>Almost insoluble</small> |- ! align="left" | <small>[[Appearance]] and [[color]]</small> | <small>Colorless liquid.<br />Odor sweet, musk, peaches, shellac</small> |- |} '''Cyclosarin''' or '''GF''' (cyclohexyl methylphosphonofluoridate) is an extremely [[Toxicity|toxic]] substance that is one of the world's most dangerous weapons of [[war]]. It is a member of the ''G-series'' family of [[nerve agent]]s, a group of [[chemical warfare|chemical weapons]] discovered and synthesized by a [[Germany|German]] team led by [[Gerhard Schrader|Dr. Gerhard Schrader]]. The major nerve gases are the G agents, [[sarin]] (GB), [[soman]], [[Tabun (nerve agent)|tabun]], and the V agents such as [[VX (nerve agent)|VX]]. The original agent, tabun, was discovered in Germany in 1936 in the process of work on [[organophosphorus]] [[insecticide]]s. Next came sarin, soman and finally the most toxic, [[VX (nerve agent)|VX]], a product of commercial insecticide laboratories prior to [[World War II]]. As a [[Chemical warfare|chemical weapon]], it is classified as a [[weapon of mass destruction]] by the [[United Nations]], according to [[UN Resolution 687]], and its production and stockpiling was outlawed by the [[Chemical Weapons Convention]] of [[1993]]. ==Chemical characteristics== Like its predecessor sarin, cyclosarin is a liquid [[organophosphate]] nerve agent. Its physical characteristics are quite different from sarin, however. At [[room temperature]], cyclosarin is a colorless liquid whose odor has been variously described as sweet and musty, or resembling [[peach]]es or [[shellac]]. Unlike sarin, cyclosarin is a ''persistent'' liquid, meaning that it has a low [[vapor pressure]] and therefore [[Evaporation|evaporates]] relatively slowly, about 69 times slower than sarin and 20 times slower than water. Also unlike sarin, cyclosarin is [[Flammability|flammable]], with a [[flash point]] of 94°C (201 °F). ==Historical notes== From [http://www.cbwinfo.com/Chemical/Nerve/GF.shtml CBWInfo.com] :''Cyclosarin was first synthesized during [[World War II]] as part of the systematic study of organophosphates undertaken by the Germans after their potential military utility was identified. It was again looked at in the early [[1950]]'s by both the [[United States]] and [[Great Britain]] as they undertook a systematic study of potential nerve agents (some U.S. sources suggest that interest in GF was stimulated by work undertaken in "another country"). However, the higher cost of the precursors for GF relative to those for GB along with its lower toxicity prevented it from being chosen for manufacture.'' :''[[Iraq]] is the only country in which large amounts of cyclosarin have ever been produced for use as a chemical warfare agent. Also Iraqis used sarin and cyclosarin as a mixture [[Iran-Iraq war|against Iran]] in 1986-1988. As with most issues surrounding the Iraqi chemical weapons programs, the basis for their decision to produce GF is somewhat unclear. However, it seems likely that the choice was driven by a combination of a desire for a more persistent agent combined with problems with obtaining alcohol precursors for [[sarin]] (due to an embargo).'' :''As noted above, [[Iraq]] also fielded weapons filled with mixtures of [[sarin]] and cyclosarin. These mixtures appear to have been produced in part for purposes of increasing persistence and in part because of raw material issues.'' ==Munitions== ===Binary weapons=== Like other nerve agents, cyclosarin can be shipped in [[Binary (chemical weapon)|binary munitions]]. A cyclosarin binary weapon would most likely contain [[methylphosphonyl difluoride]] in one capsule, with the other capsule containing either [[cyclohexanol]] or a mixture of [[cyclohexylamine]] and cyclohexanol. ===GB-GF Mixtures=== According to [http://www.cbwinfo.com/Chemical/Nerve/GF.shtml CBWInfo.com], [[Iraq]] fielded munitions filled with a mixture of GB (sarin) and GF (cyclosarin). Tests on mice indicated that GB-GF mixtures have a relative toxicity between GF and GB. ==References== * CBWInfo.com. (2003). [http://www.cbwinfo.com/Chemical/Nerve/GF.shtml Factsheets on Chemical and Biological Warfare Agents: CF]. Retrieved October 30, 2004 * United States Central Intelligence Agency. (Jul. 15, 1996). [http://www.fas.org/irp/gulf/cia/960715/72569.htm Stability of Iraq's Chemical Weapon Stockpile] Retrieved October 30, 2004 * Office of the Special Assistant for Gulf War Illnesses. (Oct. 19, 2004). [http://www.gulflink.osd.mil/khamisiyah_tech/kham_tech_tabbi.htm Chemical Properties of Sarin and Cyclosarin] Retrieved October 30, 2004 * [http://www.globalsecurity.org/military/library/news/2004/07/mil-040702-centcom01.htm Press release from Centcom] confirming that the chemical munitions found by the Poles dated back to before the 1991 Gulf War, and, thus, could not represent a threat. {{Chemical warfare}} [[Category:Anticholinesterases]] [[Category:Organophosphates]] [[Category:Organophosphinates]] [[Category:Nerve agents]] [[de:Cyclosarin]] [[ja:シクロサリン]] [[pl:Cyklosarin]]