Sarin 66390 226156256 2008-07-17T02:03:12Z Useight 2910303 Reverted edits by [[Special:Contributions/218.214.18.108|218.214.18.108]] to last version by 4.90.223.29 (using [[WP:HG|Huggle]]) {{otheruses}} {{Chembox new | Reference=<ref>{{cite web|publisher=United States Senate|work=103d Congress, 2d Session|date=[[May 25]], [[1994]]|url=http://www.gulfweb.org/bigdoc/report/appgb.html|title=Material Safety Data Sheet -- Lethal Nerve Agent Sarin (GB)|accessdate=2004-11-06}}</ref> | Name = Sarin | ImageFileL1 = Sarin-2D-skeletal.png | ImageSizeL1 = 100px | ImageFileR1 = Sarin-3D-balls.png | ImageSizeR1 = 120px | IUPACName = 2-(Fluoro-methylphosphoryl)oxypropane | OtherNames = ''O''-isopropyl methylphosphonofluoridate<br>GB | Section1 = {{Chembox Identifiers | CASNo = 107-44-8 | PubChem = 7871 | SMILES = CC(C)OP(=O)(C)F | InChI=1/C4H10FO2P/c1-4<br/>(2)7-8(3,5)6/h4H,1-3H3 }} | Section2 = {{Chembox Properties | Formula = C<sub>4</sub>H<sub>10</sub>FO<sub>2</sub>P | MolarMass = 140.09 g/mol | Appearance = Clear colorless liquid. Odorless in pure form. | BoilingPt = 158 °C | MeltingPt = -56 °C | Solubility = miscible | Density = 1.0887 g/cm³ at 25 °C<br>1.102 g/cm³ at 20 °C }} | Section3 = {{Chembox Hazards | NFPA-H = 4 | NFPA-F = 1 | NFPA-R = 1 }} }} '''Sarin''', also known by its [[NATO]] designation of '''GB''', is an extremely toxic substance whose sole application is as a [[nerve agent]]. As a [[chemical weapons|chemical weapon]], it is classified as a [[weapon of mass destruction]] by the [[United Nations]] in [[UN Resolution 687]]. Production and stockpiling of sarin was outlawed by the [[Chemical Weapons Convention]] of 1993. ==Chemical characteristics== Sarin is a fluorinated [[phosphonate]] and is similar in structure and has a similar [[mechanism of action]] as some commonly used [[insecticide]]s, such as [[malathion]]. It is similar in biological activity to [[carbamate]]s used as insecticides such as [[sevin]], and [[medicine]]s such as [[pyridostigmine]], [[neostigmine]], and [[physostigmine]]. At room temperature, sarin is a colorless, odorless liquid. Its low [[vapor pressure]] (2.9 mmHg at 20 °C) makes it relatively ineffective as a terrorist inhalation weapon. Its vapor is also colorless and odorless. It can be made more persistent through the addition of certain oils or petroleum products. Sarin can be used as a [[binary chemical weapon]]; its two precursors are [[methylphosphonyl difluoride]] and a mixture of [[isopropyl alcohol]] and [[isopropylamine]]. The isopropylamine neutralizes the [[hydrogen fluoride]] generated during the chemical reaction. ===Shelf life=== Sarin has a relatively short [[shelf life]], and will degrade after a period of several weeks to several months. The shelf life may be greatly shortened by impurities in precursor materials. According to the [[CIA]],<ref>{{cite web|publisher=United States Central Intelligence Agency|date=[[July 15]], [[1996]]|url=http://www.fas.org/irp/gulf/cia/960715/72569.htm|title=Stability of Iraq's Chemical Weapon Stockpile|accessdate=2007-08-03}}</ref> in 1989 the [[Iraqi Government]] destroyed 40 or more tons of sarin that had decomposed, and that some Iraqi sarin had a shelf life of only a few weeks, owing mostly to impure precursors. Like other nerve agents, sarin can be chemically deactivated with a strong [[alkali]]. [[Sodium hydroxide]] can be used in a [[hydrolysis]] reaction to destroy sarin, converting it to effectively harmless sodium salts.<ref>{{cite book |last=Housecroft |first=Catherine |coauthors=Sharpe, Alan G |title=Inorganic Chemistry| pages = p317 |year=2001 |isbn=0582-31080-6 }}</ref> ====Efforts to lengthen shelf life==== Nations stockpiling sarin have tried to overcome the problem of its short shelf life in three ways: * The shelf life of [[unitary]] (i.e., pure) sarin may be lengthened by increasing the purity of the precursor and intermediate chemicals and refining the production process. * Incorporating a stabilizer chemical called [[tributylamine]]. Later this was replaced by [[diisopropylcarbodiimide]] (DIC), which allowed for sarin to be stored in aluminium casings. * Developing [[binary chemical weapon]]s, where the two precursor chemicals are stored separately in the same [[Shell (projectile)|shell]], and mixed to form the agent immediately before or when the shell is in flight. This approach has the dual benefit of making the issue of shelf life irrelevant and greatly increasing the safety of sarin munitions. However, experts do not put the shelf life of this type of weapon past 5 years. ==Biological effects== [[Image:Sarin test rabbit.jpg|thumb|200px|Rabbit used to check for leaks at sarin production plant, [[Rocky Mountain Arsenal]]. (photo 1970)]] Like other nerve agents, sarin attacks the [[nervous system]] of a living organism. It is an extremely potent [[Enzyme inhibitor#Irreversible inhibitors|irreversible]] [[cholinesterase]] [[Enzyme inhibitor|inhibitor]].<ref>{{cite journal| author= Abu-Qare A. W., Abou-Donia M. B.|title= Sarin: health effects, metabolism, and methods of analysis |journal= Food Chem. Tox.|volume= 40|pages= 1327–1333 |year= 2002|doi=10.1016/S0278-6915(02)00079-0}}</ref> When a functioning pre-synaptic [[motor neuron]] or [[Parasympathetic nervous system|parasympathetic neuron]] is stimulated, it releases the [[neurotransmitter]] [[acetylcholine]] to transmit an action potential across the synaptic cleft to an effector muscle or organ. Once the action potential has been sent, the [[enzyme]] [[acetylcholinesterase]] breaks down the acetylcholine in the synaptic cleft in order to allow the effector muscle or organ to relax. Sarin disrupts the nervous system by inhibiting the cholinesterase enzyme by forming a [[covalent bond]] with the particular [[serine]] residue in the enzyme which forms the site where acetylcholine normally undergoes [[hydrolysis]]; the fluorine of the phosphonyl fluoride group reacts with the hydroxyl group on the [[serine]] side-chain, forming a [[phosphoester]] and releasing HF.<ref>{{cite web|title=Structure of acetylcholestrinase inhibited by sarin|url=http://www.rcsb.org/pdb/explore/explore.do?structureId=2JGG}}</ref> With the enzyme inhibited, acetylcholine builds up in the [[synapse]] and continues to act so that any nerve impulses are, in effect, continually transmitted. Initial symptoms following exposure to sarin are a runny nose, tightness in the chest and constriction of the [[pupil]]s. Soon after, the victim has difficulty breathing and experiences nausea and drooling. As the victim continues to lose control of bodily functions, the victim vomits, defecates and urinates. This phase is followed by twitching and jerking. Ultimately, the victim becomes comatose and suffocates in a series of convulsive spasms. Sarin has a high volatility relative to similar nerve agents. Inhalation and absorption through the skin pose a great threat. Even vapor concentrations immediately penetrate the skin. People who absorb a nonlethal dose but do not receive immediate appropriate medical treatment may suffer permanent neurological damage. Even at very low concentrations, sarin can be fatal. Death may follow in one minute after direct ingestion of about 0.01 milligram per kilogram of body weight if [[antidote]]s, typically [[atropine]] and [[pralidoxime]], are not quickly administered. [[Atropine]], an [[receptor antagonist|antagonist]] to [[muscarinic acetylcholine receptor]]s, is given to treat the physiological symptoms of poisoning. Since muscular response to acetylcholine is mediated through nicotinic acetylcholine receptors, atropine does not counteract the muscular symptoms. Pralidoxime can regenerate cholinesterases if administered within approximately five hours. It is estimated that sarin is more than 500 times more toxic than [[cyanide]].<ref>{{cite web|title=Council on Foreign Relations - Sarin|url=http://www.cfr.org/publication/9553/|accessdate=2007-08-13}}</ref> The short- and long-term symptoms experienced by those affected included: *[[coma]] *[[convulsion]]s *[[death]] *[[difficulty breathing]] *disturbed sleep and [[nightmare]]s *[[Photophobia|extreme sensitivity to light]] *foaming at the mouth *high [[fever]]s *[[influenza]]-like symptoms *[[loss of consciousness]] *[[loss of memory]] *[[nausea]] and [[vomiting]] *[[paralysis]] *[[post-traumatic stress disorder]] *respiratory problems *[[seizure]]s *uncontrollable [[trembling]] *vision problems, both temporary and permanent Although [[blood|bleeding]] from the nose and mouth were symptoms seen in the [[Sarin gas attack on the Tokyo subway|1995 sarin gas attacks in Tokyo]], this had been attributed to impurities within the sarin used as it is not usually seen.<ref>{{cite web|title=New York Times - Terror in Tokyo|url=http://query.nytimes.com/gst/fullpage.html?res=990CE0D9103AF932A15750C0A963958260|accessdate=2008-01-30}}</ref> ==History== {{seealso|Nerve agent#History}} Students at the United States Marine Corps' Nuclear, Biological and Chemical Defense School (MOS 5711) at Fort Leonard Wood in Missouri conduct a Mission Oriented Protective Posture (MOPP) chemical protective gear confidence exercise in an environment containing live Sarin (GB) gas, as well as VX nerve agent. This exercise is carried out inside of the heavily guarded Chemical Defense Training Facility (CDTF). ===Origin=== Sarin was discovered in 1938 in [[Wuppertal|Wuppertal-Elberfeld]] in [[Germany]] by two German scientists attempting to create stronger pesticides; it is the most toxic of the four [[Nerve agent#Different nerve agents|G-agents]] made by Germany. The compound, which followed the discovery of the [[nerve agent]] [[tabun (nerve agent)|tabun]], was named in honor of its discoverers: [[Gerhard Schrader|Gerhard '''S'''chrader]], '''A'''mbros, '''R'''üdiger and Van der L'''IN'''de. ===Sarin in Nazi Germany during World War II=== In mid-1939, the formula for the agent was passed to the [[chemical warfare]] section of the [[German Army Weapons Office]], which ordered that it be brought into mass production for wartime use. A number of pilot plants were built, and a high-production facility was under construction (but was not finished) by the end of [[World War II]]. Estimates for total sarin production by Nazi Germany range from 500 kg to 10 tons. Though sarin, [[tabun (nerve agent)|tabun]] and [[soman]] were incorporated into [[artillery]] shells, Germany ultimately decided not to use nerve agents against [[Allies#World War II|Allied]] targets. German [[Intelligence (information gathering)|intelligence]] was unaware that the Allies had not developed similar compounds, but they understood that unleashing these compounds would lead the Allies to develop and use chemical weapons of their own, and they were concerned that the Allies' ability to reach German targets would prove devastating in a chemical war. ===Sarin after World War II=== [[Image:Demonstration cluster bomb.jpg|thumb|U.S. [[Honest John missile]] warhead cutaway, showing M139 Sarin bomblets (c. 1960)]] * 1950s (early): [[NATO]] adopted sarin as a standard chemical weapon, and both the [[U.S.S.R]] and the [[United States]] produced sarin for military purposes. * 1953: 20-year-old [[Ronald Maddison]], a [[Royal Air Force]] engineer from [[Consett]], [[County Durham]], died in human testing of sarin at the [[Porton Down]] chemical warfare testing facility in Wiltshire. Maddison had been told that he was participating in a test to "cure the common cold." Ten days after his death an [[inquest]] was held in secret which returned a verdict of "misadventure". In 2004 the inquest was reopened and, after a 64-day inquest hearing, the jury ruled that Maddison had been unlawfully killed by the "application of a nerve agent in a non-therapeutic experiment."<ref>{{cite news |url= http://news.bbc.co.uk/1/hi/england/wiltshire/4013767.stm |publisher=BBC News Online |title=Nerve gas death was 'unlawful' |date=November 15, 2004}}</ref> * 1956: Regular production of sarin ceased in the United States, though existing stocks of bulk sarin were re-distilled until 1970. * 1960s (developing): The US unsuccessfully sought Australian permission to test Sarin and [[VX (nerve agent)|VX gas]] on 200 "mainly Australian" troops, probably in the [[Iron Range National Park|Iron Range]] rainforest near [[Lockhart River, Queensland]].<ref>Ansley, Greg (2008) [http://www.nzherald.co.nz/section/2/story.cfm?c_id=2&objectid=10520276 "US planned nerve gas attack on Australian troops"] in ''NZ Herald'', [[7 July]] 2008.</ref> * 1978: [[Michael Townley]] in a sworn declaration indicated that sarin was produced by the secret police of [[Chile]]'s [[Augusto Pinochet|Pinochet]] regime [[DINA]], by [[Eugenio Berríos]], it indicated that it was used to assassinate the state archives custodian [[Renato León Zenteno]] and the Army Corporal [[Manuel Leyton]].<ref name="">{{ cite news |url=http://diario.elmercurio.com/2006/09/19/nacional/nacional/noticias/98567EED-8253-49C6-9D0D-0C91F446EE5B.htm?id={98567EED-8253-49C6-9D0D-0C91F446EE5B} |publisher=El Mercurio |title=Townley reveló uso de gas sarín antes de ser expulsado de Chile |date=September 19, 2006 }}</ref> * 1980–1988: [[Iraq]] used sarin against [[Iran]] during the [[Iran-Iraq War|1980–88 war]]. During the 1990–91 [[Gulf War]], Iraq still had large stockpiles available which were found as coalition forces advanced north.{{Fact|date=November 2007}} * 1988: Over the span of two days in March, the ethnic [[Kurd]] city of [[Halabja]] in northern Iraq (population 70,000) was bombarded with chemical and cluster bombs, which included sarin, in the [[Halabja poison gas attack]]. An estimated 5,000 people died. * 1991: [[UN Resolution 687]] established the term "weapon of mass destruction" and called for the immediate destruction of chemical weapons in Iraq, and eventual destruction of all chemical weapons globally.<ref>[http://en.wikisource.org/wiki/United_Nations_Security_Council_Resolution_687 United Nations Security Council Resolution 687], full text at wikisource.org</ref> * 1993: The [[United Nations]] [[Chemical Weapons Convention]] was signed by 162 member countries, banning the production and stockpiling of many chemical weapons, including sarin. It went into effect on [[29 April]] [[1997]], and called for the complete destruction of all specified stockpiles of chemical weapons by April 2007.<ref>[http://www.opcw.org/html/db/cwc/eng/cwc_frameset.html Chemical Weapons Convention<!-- Bot generated title -->]</ref> * 1994: The Japanese religious sect [[Aum Shinrikyo]] released an impure form of sarin in [[Matsumoto, Nagano]]. (see [[Matsumoto incident]]) * 1995: [[Aum Shinrikyo]] sect released an impure form of sarin in the [[Tokyo Subway]]. Twelve people died. (see [[Sarin gas attack on the Tokyo subway]]) * 1998: ''[[Time Magazine]]'' and [[CNN]] ran news stories alleging that in 1970 [[U.S. Air Force]] [[A-1 Skyraider|A-1E Skyraiders]] engaged in a covert operation called [[Operation Tailwind]], in which they deliberately dropped sarin-containing weapons on U.S. troops who had defected in [[Laos]]. After investigations both internally and by the Pentagon, CNN and ''Time Magazine'' retracted the stories and fired the producers responsible.<ref>{{cite news|url=http://www.cnn.com/US/9807/21/pentagon.tailwind.02/|publisher=CNN|title=Cohen: No nerve gas used in Operation Tailwind|date=[[July 21]], [[1998]]|accessdate=2007-08-03}}</ref> * 2004: On [[May 14]] [[Iraqi insurgency]] fighters in [[Iraq]] detonated a 155 mm shell containing several litres of binary precursors for sarin. The shell was designed to mix the chemicals as it spins during flight. The detonated shell released only a small amount of sarin gas, either because the explosion failed to mix the binary agents properly or because the chemicals inside the shell had degraded significantly with age. Two [[USA|United States]] soldiers were treated for exposure after displaying the early symptoms of exposure to sarin.<ref>{{cite news|url=http://www.msnbc.msn.com/id/4997808/|title=Bomb said to hold deadly sarin gas explodes in Iraq|date=[[May 17]], [[2004]]|accessdate=2007-08-03|publisher=MSNBC}}</ref> ==References== <references/> ==External links== *[http://www.gulfweb.org/bigdoc/report/appgb.html Material Safety Data Sheet] *[http://cfrterrorism.org/weapons/sarin.html Questions and Answers for Sarin] *[http://www.fas.org/irp/gulf/cia/960715/72569.htm CIA memo: The Stability of Iraq's Chemical Weapons Stockpile] *[http://cbw.sipri.se/docu/cw-agents/sarin.html Stockholm International Peace Research Institute entry on sarin] {{Chemical warfare}} [[Category:Anticholinesterases]] [[Category:Nerve agents]] [[Category:Organophosphates]] [[Category:Organophosphinates]] [[Category:Neurotoxins]] [[Category:Toxicology]] [[Category:Chemical warfare]] [[ar:غاز السارين]] [[bs:Sarin]] [[cs:Sarin]] [[de:Sarin]] [[et:Sariin]] [[es:Gas sarín]] [[eo:Sarino]] [[fr:Sarin]] [[ko:사린]] [[it:Sarin]] [[he:סארין]] [[lv:Zarīns]] [[nl:Sarin]] [[ja:サリン]] [[no:Sarin]] [[pl:Sarin]] [[pt:Sarin]] [[ro:Zarin]] [[ru:Зарин (химическое оружие)]] [[sq:Sarina]] [[sl:Sarin]] [[fi:Sariini]] [[sv:Sarin]] [[vi:Sarin]] [[tr:Sarin]] [[zh:沙林]]