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Cyclosarin or GF (cyclohexyl methylphosphonofluoridate) is an extremely
toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...
substance used as a
chemical weapon A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...
. It is a member of the '' G-series'' family of
nerve agent Nerve agents, sometimes also called nerve gases, are a class of organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase (AChE), an enzyme that ...
s, a group of
chemical weapons A chemical weapon (CW) is a specialized Ammunition, munition that uses chemicals chemical engineering, formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be an ...
discovered and synthesized by a German team led by Dr. Gerhard Schrader. The major nerve gases are the G agents,
sarin Sarin (NATO designation GB G-series, "B"">Nerve_agent#G-series.html" ;"title="hort for Nerve agent#G-series">G-series, "B" is an extremely toxic synthetic organophosphorus compound.soman Soman (or GD, EA 1210, Zoman, PFMP, A-255, systematic name: ''O''-pinacolyl methylphosphonofluoridate) is an extremely toxic chemical substance. It is a nerve agent, interfering with normal functioning of the mammalian nervous system by inhibiti ...
(GD), tabun (GA), and the V agents such as VX. The original agent, tabun, was discovered in Germany in 1936 in the process of work on
organophosphorus Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...
insecticide Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...
s. Next came sarin, soman and finally, cyclosarin, a product of commercial insecticide laboratories prior to
World War II World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposin ...
. As a
chemical weapon A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...
, it is classified as a
weapon of mass destruction A weapon of mass destruction (WMD) is a chemical, biological, radiological, nuclear, or any other weapon that can kill and bring significant harm to numerous individuals or cause great damage to artificial structures (e.g., buildings), natura ...
by the
United Nations The United Nations (UN) is an intergovernmental organization whose stated purposes are to maintain international peace and international security, security, develop friendly relations among nations, achieve international cooperation, and be ...
. Pursuant to
UN Resolution 687 United Nations Security Council Resolution 687 was adopted on 3 April 1991. After reaffirming resolutions 660, 661, 662, 664, 665, 666, 667, 669, 670, 674, 677, 678 (all 1990) and 686 (1991), the Council set the terms, in a comprehensive resol ...
its production and stockpiling was outlawed globally by the
Chemical Weapons Convention The Chemical Weapons Convention (CWC), officially the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction, is an arms control treaty administered by the Organisation for ...
(CWC) of 1993, although Egypt, Israel, North Korea and South Sudan have not ratified the CWC (thus not outlawing their own stockpiling of chemical weapons).


Chemical characteristics

Like its predecessor
sarin Sarin (NATO designation GB G-series, "B"">Nerve_agent#G-series.html" ;"title="hort for Nerve agent#G-series">G-series, "B" is an extremely toxic synthetic organophosphorus compound.organophosphate In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered a ...
nerve agent. Its physical characteristics are, however, quite different from those of sarin. At
room temperature Colloquially, "room temperature" is a range of air temperatures that most people prefer for indoor settings. It feels comfortable to a person when they are wearing typical indoor clothing. Human comfort can extend beyond this range depending on ...
, cyclosarin is a colorless liquid whose odor has been variously described as sweet and musty, or resembling
peach The peach (''Prunus persica'') is a deciduous tree first domesticated and cultivated in Zhejiang province of Eastern China. It bears edible juicy fruits with various characteristics, most called peaches and others (the glossy-skinned, non-fu ...
es or
shellac Shellac () is a resin secreted by the female lac bug on trees in the forests of India and Thailand. It is processed and sold as dry flakes and dissolved in alcohol to make liquid shellac, which is used as a brush-on colorant, food glaze and ...
. Unlike sarin, cyclosarin is a ''persistent'' liquid, meaning that it has a low
vapor pressure Vapor pressure (or vapour pressure in English-speaking countries other than the US; see spelling differences) or equilibrium vapor pressure is defined as the pressure exerted by a vapor in thermodynamic equilibrium with its condensed phases ...
and therefore
evaporates Evaporation is a type of vaporization that occurs on the surface of a liquid as it changes into the gas phase. High concentration of the evaporating substance in the surrounding gas significantly slows down evaporation, such as when humidi ...
relatively slowly, at only about 1/69th the rate of sarin and 1/20th that of water. Also unlike sarin, cyclosarin is
flammable A combustible material is something that can burn (i.e., ''combust'') in air. A combustible material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort and a flammable mat ...
, with a
flash point The flash point of a material is the "lowest liquid temperature at which, under certain standardized conditions, a liquid gives off vapours in a quantity such as to be capable of forming an ignitable vapour/air mixture". (EN 60079-10-1) The fl ...
of 94 °C (201 °F).


History

First synthesized during
World War II World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposin ...
as part of
Nazi Germany Nazi Germany (lit. "National Socialist State"), ' (lit. "Nazi State") for short; also ' (lit. "National Socialist Germany") (officially known as the German Reich from 1933 until 1943, and the Greater German Reich from 1943 to 1945) was ...
's chemical weapons research on organophosphate compounds after their military potential was recognized, cyclosarin was also studied later in the
United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territorie ...
and
Great Britain Great Britain is an island in the North Atlantic Ocean off the northwest coast of continental Europe. With an area of , it is the largest of the British Isles, the largest European island and the ninth-largest island in the world. It is ...
in the early 1950s as part of a systematic study of potential nerve agents. It was never selected for
mass production Mass production, also known as flow production or continuous production, is the production of substantial amounts of standardized products in a constant flow, including and especially on assembly lines. Together with job production and batch ...
, however, due to its
precursors Precursor or Precursors may refer to: * Precursor (religion), a forerunner, predecessor ** The Precursor, John the Baptist Science and technology * Precursor (bird), a hypothesized genus of fossil birds that was composed of fossilized parts of un ...
being more expensive than those of other G-series nerve agents such as sarin (GB). To date, Iraq is the only nation known to have manufactured significant quantities of cyclosarin for use as a
chemical agent A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...
and to deploy it in battle. During the
Iran–Iraq War The Iran–Iraq War was an armed conflict between Iran and Iraq that lasted from September 1980 to August 1988. It began with the Iraqi invasion of Iran and lasted for almost eight years, until the acceptance of United Nations Security Council ...
(1980–1988), the Iraqis used sarin and cyclosarin together as a mixture. This was likely done to obtain a more persistent chemical agent as well as in response to an existing embargo placed on alcohol precursors for sarin.


Munitions


Binary weapons

Like other nerve agents, cyclosarin can be shipped in binary munitions. A cyclosarin binary weapon would most likely contain
methylphosphonyl difluoride Methylphosphonyl difluoride (DF), also known as EA-1251 or difluoro, is a chemical weapon precursor. Its chemical formula is CH3POF2. It is a List of Schedule 1 substances (CWC), Schedule 1 substance under the Chemical Weapons Convention. It is ...
in one capsule, with the other capsule containing a mixture of
cyclohexylamine Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, ...
and
cyclohexanol Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, whic ...
.


GB-GF mixtures

Iraq Iraq,; ku, عێراق, translit=Êraq officially the Republic of Iraq, '; ku, کۆماری عێراق, translit=Komarî Êraq is a country in Western Asia. It is bordered by Turkey to Iraq–Turkey border, the north, Iran to Iran–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

* United States Central Intelligence Agency. (July 15, 1996)
Stability of Iraq's Chemical Weapon Stockpile
Retrieved October 30, 2004 * Office of the Special Assistant for Gulf War Illnesses. (Oct. 19, 2004)

Retrieved October 30, 2004

confirming that the chemical munitions found by the Poles dated back to before the 1991 Gulf War, and, thus, could not represent a threat. {{Acetylcholine metabolism and transport modulators Acetylcholinesterase inhibitors Methylphosphonofluoridates G-series nerve agents German inventions of the Nazi period Cyclohexyl compounds