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{{short description|Chemical compound}}
{{chembox
{{About|the tear gas|the compound with the molecular formula CS|Carbon monosulfide}}
<!-- please see ] for the full template -->
{{Use dmy dates|date=June 2020}}
| verifiedrevid = 450807225
{{Use British English|date=November 2013}}
| ImageFile = CS_gas.svg
{{Chembox
| ImageSize = 200px
| data page pagename = none
| Watchedfields = changed
| verifiedrevid = 451284250
| ImageFile = CS gas.svg
| ImageSize =
| ImageName = Skeletal formula of CS gas | ImageName = Skeletal formula of CS gas
| ImageFile1 = CS-gas-3D-vdW.png | ImageFile1 = CS-gas-3D-vdW.png
| ImageSize1 = 200px | ImageSize1 =
| ImageName1 = Space-filling model of CS gas | ImageName1 = Space-filling model of CS gas
| PIN = propanedinitrile
| IUPACName = 2-Chlorobenzalmalononitrile
| OtherNames = 2-(2-Chlorobenzylidene)malononitrile<br />2-Chlorobenzalmalononitrile<br />''o''-Chlorobenzylidene malononitrile<br />Tear gas<br /><!--OCBM <br />TL-238 <br />EA-1779 unchecked unsourced-->
| OtherNames = Tear gas
<!-- 2022-01-05: from CS gas (data page), unchecked unsourced so no showing here. {{ubl|2-Chlorobenzalmalononitrile|(''o''-Chlorobenzal)malononitrile|''o''-Chlorobenzylidenemalonic nitrile|2-Chlorobenzylidenemaloninitrile|(''o''-Chlorobenzylidene)malonitrile|2-Chlorobenzylidenemalononitrile|2-(2-Chlorobenzylidene)malononitrile|(''o''-Chlorobenzylidene)malononitrile|''ortho''-Chlorobenzylidenemalononitrile|2-2-Chlorobenzylidenepropanedinitrile|2-Chloro BMN|β,β-Dicyano-''o''-chlorostyrene|NCI-C55118|Tear gas|USAF KF-11}} --->
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 4158
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16644 | ChemSpiderID = 16644
| PubChem = 17604
| EC_number = 220-278-9
| RTECS = OO3675000
| UNNumber = 2810, 3276, 2811
| UNII = D8317IAV7Q
| ChEMBL = 1256101
| InChI = 1/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H | InChI = 1/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H
| InChIKey = JJNZXLAFIPKXIG-UHFFFAOYAA | InChIKey = JJNZXLAFIPKXIG-UHFFFAOYAA
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 2698-41-1 | CASNo = 2698-41-1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 22: Line 36:
| SMILES = Clc1ccccc1\C=C(/C#N)C#N | SMILES = Clc1ccccc1\C=C(/C#N)C#N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>5</sub>Cl N<sub>2</sub><ref name="USArmy">Williams, Kenneth E. "." ''U.S. Army Center for Health Promotion and Preventive Medicine.'' Retrieved on September 23, 2007. {{Wayback|url=http://www.waco93.com/detcs.pdf|date =20070926011533|bot=DASHBot}}</ref> | Formula = C<sub>10</sub>H<sub>5</sub>ClN<sub>2</sub><ref name="USArmy">{{cite web | last = Williams | first = Kenneth E. | name-list-style = vanc | url = http://www.waco93.com/detcs.pdf | archive-url = https://web.archive.org/web/20070926011533/http://www.waco93.com/detcs.pdf | archive-date = 26 September 2007 | title = Detailed Facts About Tear Agent O-Chlorobenzylidene Malononitrile (CS)] | work = U.S. Army Center for Health Promotion and Preventive Medicine }}</ref>
| MolarMass = 188.6&nbsp;g/mol<ref name=UweHeinrich>Heinrich, U. "." ''.''] September 2000. Retrieved on September 23, 2007</ref> | MolarMass = 188.6&nbsp;g/mol<ref name=UweHeinrich>{{cite web | vauthors = Heinrich U | url = http://www.veritagiustizia.it/docs/gas_cs/CS_Effects_Waco.pdf | title = Possible lethal effects of CS tear gas on Branch Davidians during the FBI raid on the Mount Carmel compound near Waco, Texas | date = September 2000 | access-date = 23 September 2007 | archive-date = 25 December 2014 | archive-url = https://web.archive.org/web/20141225230238/http://www.veritagiustizia.it/docs/gas_cs/CS_Effects_Waco.pdf | url-status = live }}</ref>
| Appearance = White crystalline powder<br />Colourless gas when burned | Appearance = White crystalline powder<br />Colourless gas when burned
| Odor = Pepper-like<ref name=PGCH />
| Density = 1.04&nbsp;g/cm<sup>3</sup> | Density = 1.04&nbsp;g/cm<sup>3</sup>
| MeltingPtC = 93
| MeltingPt = 93°C, (366.15 K), (199.4&nbsp;°F)
| MeltingPt_notes =
| BoilingPt = 310&nbsp;°C, (583.15 K), (590&nbsp;°F)<ref>{{cite book|url=http://books.google.com/?id=y2FwGRVMW5kC&pg=PA138|page=138|title=Compendium of Chemical Warfare Agents|author=Hoenig, Steven L.|publisher=Springer|year=2006|isbn=0387346260}}</ref>
| BoilingPtC = 310
| VaporPressure = (mm ]) 3.4 × 10<sup>−5</sup> at 20&nbsp;°C}}
| BoilingPt_ref = <ref>{{cite book|url=https://books.google.com/books?id=y2FwGRVMW5kC&pg=PA138|page=138|title=Compendium of Chemical Warfare Agents|author=Hoenig, Steven L.|publisher=Springer|year=2006|isbn=978-0-387-34626-7}}</ref>
| Section7 = {{Chembox Hazards
| VaporPressure = 3.4×10<sup>−5</sup>{{nbsp}}] at 20&nbsp;°C
| Solubility = Insoluble
}}
|Section7={{Chembox Hazards
| NFPA-H = 2 | NFPA-H = 2
| NFPA-F = 1 | NFPA-F = 1
| NFPA-R = 0}} | NFPA-R = 0
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| Section8 = {{Chembox Related
| GHSSignalWord = Danger
| OtherCpds =
| HPhrases = {{H-phrases|302|314|330|335|372|410}}
| 5-chloro-2-quinolinecarbonitrile <br /> 6-chloro-2-quinolinecarbonitrile <br /> 7-chloro-2-quinolinecarbonitrile}}
| PPhrases = {{P-phrases|260|261|264|270|271|273|280|284|301+312|301+330+331|303+361+353|304+340|305+351+338|310|312|314|320|321|330|363|391|403+233|405|501}}
| PEL = TWA 0.05{{nbsp}}ppm (0.4{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0122}}</ref>
| IDLH = 2{{nbsp}}mg/m<sup>3</sup><ref name=PGCH />
| REL = C 0.05{{nbsp}}ppm (0.4{{nbsp}}mg/m<sup>3</sup>) <ref name=PGCH />
| LCLo = {{ubl
| 1806{{nbsp}}mg/m<sup>3</sup> (rat, 45{{nbsp}}min)
| 2753{{nbsp}}mg/m<sup>3</sup> (mouse, 20{{nbsp}}min)
| 1802{{nbsp}}mg/m<sup>3</sup> (rabbit, 10{{nbsp}}min)
| 2326{{nbsp}}mg/m<sup>3</sup> (guinea pig, 10{{nbsp}}min)<ref>{{IDLH|2698411|o-Chlorobenzylidene malononitrile}}</ref>
}}
}} }}
|Section8={{Chembox Related
| OtherCompounds =
5-chloro-2-quinolinecarbonitrile <br /> 6-chloro-2-quinolinecarbonitrile <br /> 7-chloro-2-quinolinecarbonitrile}}
}}
The compound '''2-chlorobenzalmalononitrile''' (also called '''''o''-chlorobenzylidene malononitrile'''; chemical formula: C<sub>10</sub>H<sub>5</sub>ClN<sub>2</sub>), a ], is the defining component of the ] commonly referred to as '''CS gas''', a ] which is used as a ], and is banned for use in warfare due to the ].

Exposure causes a burning sensation and tearing of the eyes to the extent that the subject cannot keep their eyes open, and a burning irritation of the mucous membranes of the nose, mouth and throat, resulting in profuse coughing, nasal mucus discharge, disorientation, and difficulty breathing, partially incapacitating the subject. CS gas is an ] of a ] ] (a substance that dissolves other active substances and that easily evaporates) and 2-chlorobenzalmalononitrile, which is a solid compound at room temperature. CS gas is generally accepted as being ].


==History==
'''2-chlorobenzalmalononitrile''' (also called o-chlorobenzylidene malononitrile) (chemical formula: C<sub>10</sub>H<sub>5</sub>ClN<sub>2</sub>) is the defining component of a "]" commonly referred to as '''CS gas,''' which is used as a ]. "CS gas" is actually an ] of a ] ] (a substance that dissolves other active substances and that easily evaporates with it) and 2-chlorobenzalmalononitrile, which is a solid compound at room temperature. CS gas is generally accepted as being ]. It was discovered by two Americans, Ben Corson and Roger Stoughton, at ] in 1928, and the chemical's name is derived from the first letters of the scientists' surnames.<ref>{{OED|CS}}</ref><ref name="Name">"." ''.'' Retrieved on September 23, 2007</ref>
CS gas was first ] by two Americans, Ben Corson and Roger Stoughton,<ref name=corson28>{{cite journal| last1 = Corson| first1 = Ben B.| last2 = Stoughton| first2 = Roger W. | name-list-style = vanc | year = 1928| title = Reactions of Alpha, Beta-Unsaturated Dinitriles| journal = Journal of the American Chemical Society| volume = 50| issue = 10| pages = 2825–2837 | doi = 10.1021/ja01397a037}}</ref> at ] in ] in 1928, and the chemical's name is derived from the first letters of the scientists' surnames.<ref>{{OED|CS}}</ref><ref name="Name">" {{Webarchive|url=https://web.archive.org/web/20051219182423/http://columbia.thefreedictionary.com/Cs |date=19 December 2005 }}". {{Webarchive|url=https://web.archive.org/web/20050729031936/http://columbia.thefreedictionary.com/ |date=29 July 2005 }}. Retrieved on 23 September 2007.</ref>


CS was developed and tested secretly at ] in ], England, in the 1950s and 1960s. CS was used first on animals, then subsequently on ] servicemen volunteers. Notably, CS has a limited effect on animals due to "under-developed tear-ducts and protection by fur".<ref name=Zarc>"." ''.'' Retrieved on September 23, 2007</ref> CS was developed and tested secretly at ] in ], UK, in the 1950s and '60s. CS was used first on animals, and subsequently on ] servicemen volunteers. CS has less effect on animals because they have different tear ducts and, in the case of non-human mammals, their fur inhibits the free entry of the gas.<ref name=Zarc>" {{Webarchive|url=https://web.archive.org/web/20061128091426/http://www.zarc.com/english/tear_gases/csmain.html |date=28 November 2006 }}". Zarc International. Retrieved on 23 September 2007</ref>


As recently as 2002, the U.S. State Department ] of ] made a firm distinction between "riot-control agents" such as CS gas, and "lethal chemical weapons." The Bureau cited support for this position from the U.K. and Japan.<ref name=s2002>{{cite web |url=https://2009-2017.state.gov/t/isn/4784.htm |title=Protocol for the Prohibition of the Use in War of Asphyxiating, Poisonous or Other Gases and of Bacteriological Methods of Warfare (Geneva Protocol) |publisher=U.S. Department of State |date=25 September 2002 |access-date=24 August 2013}}</ref>
==Production==

CS is ] by the reaction of 2-chlorobenzaldehyde and ] via the ]:
The use of CS in warfare has been prohibited under the ].<ref>{{Cite web |title=Article II – Definitions and Criteria |url=https://www.opcw.org/chemical-weapons-convention/articles/article-ii-definitions-and-criteria |access-date=2024-11-25 |website=OPCW |language=en}}</ref> The ] (the governing body of the convention) has observed its use in the ] in 2024.<ref>{{Cite web |title=OPCW issues report on its Technical Assistance Visit to Ukraine following an alleged incident of use of toxic chemicals as a weapon |url=https://www.opcw.org/media-centre/news/2024/11/opcw-issues-report-its-technical-assistance-visit-ukraine-following |access-date=2024-11-25 |website=OPCW |language=en}}</ref><ref>{{Cite web |date=2024-11-18 |title=Tear gas used on Ukraine battlefield, chemical weapons agency finds |url=https://www.reuters.com/world/europe/tear-gas-used-ukraine-battlefield-chemical-weapons-agency-finds-2024-11-18/ |publisher=]}}</ref>
]

== Production ==
CS is ] by the reaction of ] and ] via the ]:
]
::ClC<sub>6</sub>H<sub>4</sub>CHO + ] → ClC<sub>6</sub>H<sub>4</sub>CHC(CN)<sub>2</sub> + H<sub>2</sub>O ::ClC<sub>6</sub>H<sub>4</sub>CHO + ] → ClC<sub>6</sub>H<sub>4</sub>CHC(CN)<sub>2</sub> + H<sub>2</sub>O


The reaction is catalysed with weak base like ] or ]. The production method has not changed since the substance was discovered by Corson and Stoughton.<ref name="corson">{{cite journal|author= Corson BB, Stoughton RW| title=Reactions of Alpha, Betha-Unsaturated Dinitriles|journal=J Am Chem Soc|year= 1928|volume=50|pages=2825–2837|doi=10.1021/ja01397a037|issue= 10}}</ref> Other bases, solvent free methods and ] promotion have been suggested to improve the production of the substance.<ref>{{cite journal|author= Pande A, Ganesan K, Jain AK, Gupta PK, Malhotr RC| title=Novel Eco-Friendly Process for the Synthesis of 2-Chlorobenzylidenemalononitrile and ITS Analogues Using Water As a Solvent|journal=Org Proc Res Develop|year= 2005|volume=9|pages=133–136| doi=10.1021/op0498262|issue= 2}}</ref> The reaction is catalysed with a weak base like ] or ]. The production method has not changed since the substance was discovered by Corson and Stoughton.<ref name="corson">{{cite journal|vauthors= Corson BB, Stoughton RW| title=Reactions of Alpha, Betha-Unsaturated Dinitriles|journal=J Am Chem Soc|year= 1928|volume=50|pages=2825–2837|doi=10.1021/ja01397a037|issue= 10}}</ref> Other bases, solvent free methods and ] promotion have been suggested to improve the production of the substance.<ref>{{cite journal|vauthors= Pande A, Ganesan K, Jain AK, Gupta PK, Malhotr RC| title=Novel Eco-Friendly Process for the Synthesis of 2-Chlorobenzylidenemalononitrile and ITS Analogues Using Water As a Solvent|journal=Org Proc Res Develop|year= 2005|volume=9|pages=133–136| doi=10.1021/op0498262|issue= 2}}</ref>


The physiological properties had been discovered already by the chemists first synthesising the compound in 1928: The physiological properties had been discovered already by the chemists first synthesising the compound in 1928:
"Physiological Properties. Certain of these dinitriles have the effect of sneeze and tear gases. They are harmless when wet but to handle the dry powder is disastrous. (])"<ref name="corson"/> "Physiological Properties. Certain of these dinitriles have the effect of sneeze and tear gases. They are harmless when wet but to handle the dry powder is disastrous."<ref name="corson" />


===Use as an aerosol=== === Use as an aerosol ===


As 2-chlorobenzalmalononitrile is a solid at room temperature, not a ], a variety of techniques have been used to make this solid usable as an ]: As 2-chlorobenzalmalononitrile is a solid at room temperature, not a ], a variety of techniques have been used to make this solid usable as an ]:


*Melted and sprayed in the molten form. * Melted and sprayed in the molten form.
*Dissolved in organic solvent. * Dissolved in organic solvent.
*CS<sub>2</sub> dry powder (CS<sub>2</sub> is a ]ized, micro-pulverized form of CS). * CS2 dry powder (CS2 is a ]ized, micro-pulverized form of CS).
*CS from thermal grenades by generation of hot gases.<ref name=UweHeinrich/> * CS from thermal grenades by generation of hot gases.<ref name=UweHeinrich />


In the ], CS was dissolved in the organic solvent ] (also known as methylene chloride). The solution was dispersed as an ] via explosive force and when the highly volatile dichloromethane evaporated, CS crystals precipitated and formed a fine dispersion in the air.<ref name=UweHeinrich/> In the ] in the United States, CS was dissolved in the organic solvent ] (also known as methylene chloride). The solution was dispersed as an ] via explosive force and when the highly volatile dichloromethane evaporated, CS crystals precipitated and formed a fine dispersion in the air.<ref name=UweHeinrich />


==Effects== == Effects ==
]
Many types of tear gas and other riot control agents have been produced with effects ranging from mild tearing of the eyes to immediate ] and ]. ] and CS are the most widely used and known, but around 15 different types of tear gas have been developed worldwide, e.g. ] or ], CNB, and CNC. CS has become the most popular due to its strong effect. The effect of CS on a person will depend on whether it is packaged as a solution or used as an ]. The size of solution droplets and the size of the CS ]s after evaporation are factors determining its effect on the human body.<ref name="Ineffective">"." ''Police Complaints Authority.'' Retrieved on 23 September 2007</ref>


The chemical reacts with moisture on the skin and in the eyes, causing a burning sensation and the immediate forceful and uncontrollable shutting of the eyes. Effects usually include tears streaming from the eyes, profuse coughing, exceptional nasal discharge that is full of mucus, burning in the eyes, eyelids, nose and throat areas, disorientation, dizziness and restricted breathing. It will also burn the skin where sweaty or sunburned. In highly concentrated doses, it can also induce severe coughing and vomiting. Most of the immediate effects wear off within a few hours (such as exceptional nasal discharge and profuse coughing), although respiratory, gastrointestinal, and oral symptoms may persist for months.<ref>{{cite journal | vauthors = Karagama YG, Newton JR, Newbegin CJ | title = Short-term and long-term physical effects of exposure to CS spray | journal = Journal of the Royal Society of Medicine | volume = 96 | issue = 4 | pages = 172–4 | date = April 2003 | pmid = 12668703 | pmc = 539444 | doi = 10.1177/014107680309600404 }}</ref><ref>{{cite journal | vauthors = Torgrimson-Ojerio BN, Mularski KS, Peyton MR, Keast EM, Hassan A, Ivlev I | title = Health issues and healthcare utilization among adults who reported exposure to tear gas during 2020 Portland (OR) protests: a cross-sectional survey | journal = BMC Public Health | volume = 21 | issue = 1 | pages = 803 | date = April 2021 | pmid = 33902512 | pmc = 8074355 | doi = 10.1186/s12889-021-10859-w | doi-access = free }}</ref> Excessive exposure can cause chemical burns resulting in permanent scarring.<ref> {{Webarchive|url=https://web.archive.org/web/20160305124551/http://news.bbc.co.uk/2/hi/uk_news/england/dorset/4674350.stm |date=5 March 2016 }}. ''].'' 2 February 2006. Retrieved on 23 September 2007</ref>
Many types of tear gas and other riot control agents have been produced with effects ranging from mild tearing of the eyes to immediate ] and ]. ] and CS are the most widely used and known, but around 15 different types of tear gas have been developed worldwide e.g. ] or ], CNB, and CNC. CS has become the most popular due to its strong effect and lack of toxicity in comparison with other similar chemical agents. The effect of CS on a person will depend on whether it is packaged as a solution or used as an ]. The size of solution droplets and the size of the CS ]s after evaporation are factors determining its effect on the human body.<ref name="Ineffective">"." ''Police Complaints Authority.'' Retrieved on September 23, 2007</ref>


Adults exposed to tear gas during the 2020 protests in Portland, Oregon, US also reported menstrual changes (899; 54.5% of 1650 female respondents). Exposure to tear gas is associated with avoidable healthcare utilization.<ref>{{cite journal | vauthors = Torgrimson-Ojerio BN, Mularski KS, Peyton MR, Keast EM, Hassan A, Ivlev I | title = Health issues and healthcare utilization among adults who reported exposure to tear gas during 2020 Portland (OR) protests: a cross-sectional survey | journal = BMC Public Health | volume = 21 | issue = 1 | pages = 803 | date = April 2021 | pmid = 33902512 | pmc = 8074355 | doi = 10.1186/s12889-021-10859-w | doi-access = free }}</ref>
The chemical reacts with moisture on the skin and in the eyes, causing a burning sensation and the immediate forceful and uncontrollable shutting of the eyes. Effects usually include tears streaming from the eyes, coughing, running nose full of mucus, burning in the nose and throat areas, disorientation, dizziness and restricted breathing. It will also burn the skin where sweaty and or sunburned. In highly concentrated doses it can also induce severe coughing and vomiting. Almost all of the immediate effects wear off in a matter of minutes.


=== Secondary effects ===
==Toxicity==
People or objects contaminated with CS gas can cause secondary exposure to others, including healthcare professionals and ]. In addition, repeated exposure may cause ].<ref>{{cite journal | vauthors = Carron PN, Yersin B | title = Management of the effects of exposure to tear gas | journal = BMJ | volume = 338 | pages = b2283 | date = June 2009 | pmid = 19542106 | doi = 10.1136/bmj.b2283 | s2cid = 7870564 }}</ref>
]' mural of a boy running from CS gas in ].]]


== Toxicity ==
Although described as a non-lethal weapon for crowd control, many studies have raised doubts about this classification. As well as creating severe pulmonary damage, CS can also significantly damage the heart and liver.<ref name=AMA>{{cite journal |author=Hu, Howard ''et al.'' |journal=Journal of the American Medical Association |year=1989 |title=The Use of Chemical Weapons: Conducting an Investigation Using Survey Epidemiology |volume=262 |issue=5 |pages=640–3 |url=http://jama.ama-assn.org/content/262/5/640.abstract |pmid=2746816 |doi=10.1001/jama.262.5.640}}</ref>


] (Transient Receptor Potential-Ankyrin 1) ion channel expressed on ] (especially ]) has been implicated as the site of action for CS gas in rodent models.<ref>{{cite journal | vauthors = Bessac BF, Sivula M, von Hehn CA, Caceres AI, Escalera J, Jordt SE | title = Transient receptor potential ankyrin 1 antagonists block the noxious effects of toxic industrial isocyanates and tear gases | journal = FASEB Journal | volume = 23 | issue = 4 | pages = 1102–14 | date = April 2009 | pmid = 19036859 | pmc = 2660642 | doi = 10.1096/fj.08-117812 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Brône B, Peeters PJ, Marrannes R, Mercken M, Nuydens R, Meert T, Gijsen HJ | title = Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor | journal = Toxicology and Applied Pharmacology | volume = 231 | issue = 2 | pages = 150–6 | date = September 2008 | pmid = 18501939 | doi = 10.1016/j.taap.2008.04.005 }}</ref>
On September 28, 2000, Prof. Dr. Uwe Heinrich released a study commissioned by ], of the ], to investigate the use of CS by the FBI at the ]' Mount Carmel compound. He concluded that the lethality of CS used would have been determined mainly by two factors: whether gas masks were used and whether the occupants were trapped in a room. He suggests that if no gas masks were used and the occupants were trapped, then, "...there is a distinct possibility that this kind of CS exposure can significantly contribute to or even cause lethal effects."<ref name=UweHeinrich/>


Although described as a ] for crowd control, studies have raised doubts about this classification. CS can cause severe ] damage and can also significantly damage the heart and liver.<ref name="AMA">{{cite journal | vauthors = Hu H, Fine J, Epstein P, Kelsey K, Reynolds P, Walker B | title = Tear gas--harassing agent or toxic chemical weapon? | journal = JAMA | volume = 262 | issue = 5 | pages = 660–3 | date = August 1989 | pmid = 2501523 | doi = 10.1001/jama.1989.03430050076030 }}</ref>
Many reports have associated CS exposure with miscarriages.<ref name=AMA/> This is consistent with its reported ] effect (abnormal chromosome change) on mammalian cells.


On 28 September 2000, Prof. Dr. Uwe Heinrich released a study commissioned by ], of the ], to investigate the use of CS by the FBI at the ]' Mount Carmel compound. He said no human deaths had been reported, but concluded that the lethality of CS used would have been determined mainly by two factors: whether gas masks were used and whether the occupants were trapped in a room. He suggests that if no gas masks were used and the occupants were trapped, then, "there is a distinct possibility that this kind of CS exposure can significantly contribute to or even cause lethal effects".<ref name=UweHeinrich />
When CS is metabolized, ] can be detected in human tissue.<ref name=AMA/> According to the United States Army Center for Health Promotion and Preventive Medicine, CS emits "very toxic fumes" when heated to decomposition, and at specified concentrations CS gas is an immediate danger to life and health. They also state that those exposed to CS gas should seek medical attention immediately.<ref name="USArmy"/>


CS gas can have a ]ic effect (abnormal chromosome change) on mammalian cells, but no studies have linked it to miscarriages or stillbirths.<ref name=AMA /><!-- Quote: "Only one study (27) has assessed the effect of CS on pregnancy in animals and itfound no significant effect. The Himsworth committee (5) found no signficant increase in abortions, stillbirths, or congenital abnormalities in geographic districts of tear gas use, comparing a 9-month period of heavy tear gas exposure to aprevious 9-month period. " --> In Egypt, CS gas was reported to be the cause of death of several protesters in Mohamed Mahmoud Street near ] during the November 2011 protests. The solvent in which CS is dissolved, ] (MIBK), is classified as harmful by inhalation; irritating to the eyes and respiratory system; and repeated exposure may cause skin dryness or cracking.<ref>{{cite web|title=MSDS for 99% 4-Methyl-2-pentanone (MIBK)|url=https://www.alfa.com/en/content/msds/british/A11618.pdf|publisher=Alfa Aesar|access-date=7 January 2013|archive-url=https://web.archive.org/web/20180816093639/https://www.alfa.com/en/content/msds/british/A11618.pdf|archive-date=16 August 2018}}</ref>
In Israel, CS gas was reported to be the cause of death of ] on December 31, 2010,<ref>{{cite news|url=http://www.haaretz.com/news/diplomacy-defense/bil-in-protester-dies-after-exposure-to-tear-gas-shot-by-idf-1.334627|title=Bil'in protester dies after exposure to tear gas shot by IDF|work=Haaretz|date=December 31, 2010}}</ref> although the ] have questioned the veracity of the report.


== See also ==
It has been noted that the solvent MiBK is itself harmful, and can cause inflammation, dermatitis, burns to the skin and liver damage.<ref name="MiBk">"." ''.'' Last Updated on June 16, 2005. Retrieved on September 23, 2007. {{Wayback|url=http://physchem.ox.ac.uk/MSDS/|date =20070925061745|bot=DASHBot}}</ref>


* ]
==Decontamination==
* ]
CS contamination can be removed by washing with an ] solution of water and 5% ].<ref name=Zarc/><ref>{{cite journal|doi=10.1111/j.1365-2044.1993.tb07424.x|title=CS gas?implications for the anaesthetist|year=1993|author=Bhattacharya, S. T.|journal=Anaesthesia|volume=48|page=896|pmid=8238834|last2=Hayward|first2=AW|issue=10}}</ref>
* ]
* ]
* ]
* ]
* ]s


==Use== == References ==
] Polish tear gas grenade launcher.]]
].]]


{{Reflist}}
CS is used in spray form by many police forces as a temporary incapacitant and to subdue attackers or persons who are violently aggressive. Officers that are trained in the use and application of CS spray are routinely exposed to it as part of their training.


== External links ==
Recently, blank pistol cartridges carrying CS in powder form have been released to public. These, when fired in relatively close ranges, fully expose the target to the effects of CS, and are employed as a potent defensive weapon in regions where blank firing pistols are legally permitted for such use.


{{Commons category|CS gas}}
Although predominantly used by police it has also been used in criminal attacks in various countries.<ref name="GuardianCrime">Kelso, Paul. "." ''].'' October 1, 1999. Retrieved on September 23, 2007</ref><ref name="CrimeDublin">Condon, Deborah. "." ''.'' May 14, 2004. Retrieved on September 23, 2007</ref><ref name="BBCcrimeShop">"." ''].'' December 1, 2005. Retrieved on September 23, 2007</ref><ref name="BBCcrimeCar">"." ''].'' January 4, 2006. Retrieved on September 23, 2007</ref>


*
Use of CS in war is prohibited under the terms of the 1997 ], signed by most nations in 1993 with all but five other nations signing between the years of 1994 through 1997. The reasoning behind the prohibition is pragmatic: use of CS by one combatant could easily trigger retaliation with much more toxic chemical weapons such as ]s. Only five nations have not signed the Chemical Weapons Convention and are therefore unhindered by restrictions on the use of CS gas: ], ], ], ], and ].<ref name=untc>United Nations Treaty Collection. ''''. Retrieved 19 January 2009.</ref>
* {{cite journal | vauthors=Carron PN, Yersin B | title=Management of the effects of exposure to tear gas | journal=BMJ | volume=338 | issue=7710 | pages=b2283 | date=June 2009 | pmid=19542106 | doi=10.1136/bmj.b2283 | s2cid=7870564 |ref=none}}

*
Domestic police use of CS is legal in many countries, however, as the Chemical Weapons Convention prohibits only military use.
* ]

*
===Cyprus===
* A Paper prepared by the Steering Group led by the Northern Ireland Office – April 2001
CS was first tested in the field by the British army in ] in 1958. At this time it was known by the code name '''T792'''.<ref name="Cyprus">"." Retrieved on September 23, 2007</ref>
* statement on 2-chlorobenzylidene malononitrile (CS) and CS spray, September 1999. (pdf)

* Noxious Tear-Gas Bomb Mightier in Peace than in War.
===Iraq===
* – The Omega Foundation (pdf)
Iraq successfully developed CS during the 1970s and during the 1980s produced tons of the substance firstly at ] and later at al-Muthanna.<ref name="IraqWatch">"." ''.'' Retrieved on September 23, 2007</ref> Then-Iraqi leader ] ordered troops to use nerve agents against Iraqi ] in his own country and against ] during the ]. It is believed that Iraqi forces used multiple ] during the attack, including ] and the ]s ], ], ] and ];<ref>. Dlawer.net. Retrieved on 2011-02-02.</ref> some sources have also pointed to the ] ].
*
{{Main|Halabja poison gas attack}}

], acting as an agent of the United States, deployed CS in the ] from a helicopter hovering over a checkpoint in the ] in ].<ref name="New York Times">{{cite news|url=http://www.nytimes.com/2008/01/10/world/middleeast/10blackwater.html|title=2005 Use of Gas by Blackwater Leaves Questions|accessdate=2009-08-08|work=The New York Times|first=James|last=Risen|date=January 10, 2008}}</ref>

===Israel===
] forces spray CS gas at riot control situations. It is widely used at ] within the ] and at the ] as a non-lethal weapon.<ref>{{cite news|url=http://www.israel-palestinenews.org/2009/08/four-palestinians-faint-after-inhaling.html|title=Four Palestinians faint after inhaling CS gas|date=August 8, 2009}}</ref><ref>{{cite news|url=http://www.maannews.net/eng/ViewDetails.aspx?ID=220682|title=Dozens hit by CS gas during anti-wall demonstrations|date=August 22, 2009}}</ref>

===Philippines===
CS tear gas was used in suppression of the mutiny in Makati that was led by ]. The tear gas was fired in the building and all the people in the building including reporters were affected.

===Sri Lanka===
The ], also known as ] of ], an ] group in Sri Lanka used CS gas against government forces that were on an offensive to flush and defeat these insurgents during September 2008.<ref>{{cite web
|url=http://lankadailynews.com/2008/09/ltte-cs-gas-attack-soldiers/
|title=LTTE used CS Gas to attack Soldiers
|publisher=Lanka Daily News
|date=September 18, 2008
|accessdate=2011-01-04}}</ref> Its use hindered the army's progress but ultimately proved ineffective in preventing the army from overrunning LTTE positions.

This is one of the first few cases of insurgents using CS gas as an insurgent weapon.

===United Kingdom===
====Northern Ireland====
], August 1969.]]

CS gas was used extensively in the ] area of ], ] during the "]", a two-day riot in August, 1969. A total of 1,091 canisters containing 12.5g of CS each, and 14 canisters containing 50g of CS each, were released in the densely populated residential area.<ref name="Bsunday">{{cite book|author=Dr Raymond McClean|title=The Road To Bloody Sunday (revised edition)| location=Guildhall|publisher=Printing Press|year=1997|isbn=0-946451-37-0}} </ref> On 30 August the ] was set up to investigate the medical effects of its use in Derry. Its conclusions, viewed in the political context of the time, still pointed towards the necessity of further testing of CS gas before being used as a riot control agent. During the rioting in ], the following year, known as the ], the Army fired up to 1,600 canisters into the densely populated ] area. It was also used in ] on 9 July 1972 on the breakdown of the IRA ceasefire. Not long after, the British Army and RUC ceased using CS in Northern Ireland. Up to this point, it had been used in crowd control scenarios in Derry and ].

====Great Britain====
The first use of CS gas on the UK mainland, which was not part of military training, was carried out in 1944 during a hostage siege at a North London address. Soldiers were asked to throw CS grenades through the skylight in hope of bringing the incident to a speedy conclusion, however, the hostage-taker had brought his civilian-issue gas mask with him, negating the effect.{{Citation needed|date=September 2011}}

The siege of Trough Gate, in Oldham, during 1973 was the second use of CS gas on UK Mainland. It was applied to the rear of a van where the chief suspect was hiding. The suspect committed suicide with the handgun he was armed with.

The first use of CS tear gas to quell rioting in mainland Britain was in the ] area of ] in 1981.<ref name="BBCtoxteth">"." ''].'' Retrieved on September 23, 2007</ref>

CS gas incapacitant sprays were first introduced into the ] in 1995, to assist them in dealing with violent incidents.<ref name="BMJpolice">{{cite journal|author=Euripidou E, MacLehose R, Fletcher A|title=An investigation into the short term and medium term health impacts of personal incapacitant sprays. A follow up of patients reported to the National Poisons Information Service (London)|journal=Emerg Med J|year=2004|pages=548–52|volume=21|issue=5|pmid=15333526|doi=10.1136/emj.2003.012773|pmc=1726417}}</ref> The CS is in the form of a hand-held aerosol canister, with the solution being 5% CS, with ] as the solvent, which is propelled by pressurized ]. The liquid stream is directed where the user points the canister, being accurate up to 4 metres. All forces dictate that for an officer to be authorised to carry CS, they have to have completed a training course in the spray's use. Under ] CS and other incapacitant sprays are classed as prohibited weapons, making it unlawful for a member of the public to possess such an item. In recent years, some forces have stopped using CS, in favour of the new ].<ref>{{cite news|url=http://www.acpo.police.uk/policies.asp|title=INCAPACITANT SPRAY: Guidance on the Use of Incapacitant Spray|date=May 2009|publisher=Association of Chief Police Officer of England, Wales & Northern Ireland}}</ref>

A six month trial by sixteen police forces in England began on the 1 March 1996. Only two weeks later, on 16 March 1996, a ]n ], Ibrahima Sey was taken to ] Police Station in east London. Whilst incapacitating the man, police sprayed him with CS and held him on the ground for over 15 minutes, and he subsequently died. Although a verdict of ] was given by the jury at the end of the inquest into his death, no charges were brought against any member of the police force.<ref name="Inquest">"." ''Inquest.'' 1997</ref>

The ] that do use the PIS in the UK require that the personnel undergoing training should themselves be sprayed with a 3% dissolved CS, during self-defense training, in order for them to be able to be authorized to carry it as ]. They are also trained in helping the incapacitated person recover quickly once successfully restrained. Most forces currently issue CS spray to its officers, but there has been a recent move for a few forces to issue PAVA Spray ( aka ]).

The CS spray used by UK police is five times more concentrated than the spray used by American police forces (5% dissolved CS and 1% CS respectively).<ref name="BMJstrength">{{cite journal|author=Southward RD|title=CS incapacitant spray|journal=J Accid Emerg Med|year=2000|page=76|volume=17|issue=1|pmid=10659007|url=http://emj.bmjjournals.com/cgi/content/full/17/1/76-a|pmc=1756282}}</ref>

In 1999 the UK mental health charity ] called for a suspension in its use until it is fully tested and there is proof that CS is safe.<ref name="BBCmind">"." ''].'' September 24, 1999. Retrieved on September 23, 2007</ref>

In February 2006, there were calls to have CS spray banned in the UK after Dan Ford, from Wareham in ], was permanently facially scarred after being sprayed in the face with a police CS canister. Mr Ford was subsequently advised by doctors to stay out of sunlight for at least 12 months. After the incident, his cousin, Donna Lewis, was quoted as saying, "To look at him, it was like looking at a melting man, with liquid oozing from his face."<ref name = "BBCDanFord">"." ''].'' February 2, 2006. Retrieved on September 23, 2007</ref> However, it has not yet been confirmed that Mr Ford's injury was a reaction to having been exposed to police CS spray, or whether an unrelated chemical exposure caused the injury. An investigation is ongoing.

In January 2011, CS was used by the ] at a ] protest in ].<ref name = "Guardian">. Guardian. Retrieved on 2011-02-02.</ref><ref name = "BBC News">. Bbc.co.uk. Retrieved on 2011-02-02.</ref>

The ] use CS gas annually to test their ] equipment. During initial training they introduce recruits to CS gas by ordering them into a small enclosed space known as a Respirator Test Facility (RTF) and igniting chemical tablets to induce CS production. After recruits have carried out their ] drills, they must remove their respirators and inhale the CS to realise it effects and become confident their masks work.{{Failed verification|date=July 2011}} <ref>. Ong.ohio.gov. Retrieved on 2011-02-02.</ref><ref>. Cottonbalers. Retrieved on 2011-02-02.</ref>

===United States===
CS is used by many police forces within the United States. It was most famously used as one of a number of techniques by ] law enforcement officials in the 1993 ].<ref name="waco">"." ''].'' 1995. Retrieved on September 23, 2007</ref>

Riot police in ] in September, 2009 used CS gas and ] techniques to disperse assemblies in the vicinity of the ].

In Berkeley, California during the ] events in ] on Wednesday, May 21, 1969, a midday memorial was held for student James Rector, a non-protester shot to death by police, at Sproul Plaza on the University campus. In his honor, several thousand people peacefully assembled to listen to speakers remembering his life. Without warning, National Guard troops surrounded Sproul Plaza, donned their gas masks, and pointed their bayonets inward, while helicopters dropped CS gas directly on the trapped crowd. No escape was possible, and the gas caused acute respiratory distress, disorientation, temporary blindness and vomiting. Many people, including children and the elderly, were injured during the ensuing panic. The gas was so intense that breezes carried it into Cowell Memorial Hospital, endangering patients, interrupting operations and incapacitating nurses. Students at nearby Jefferson and Franklin elementary schools were also affected.<ref>. TIME (1969-05-30). Retrieved on 2011-02-02.</ref><ref>. Fsmitha.com. Retrieved on 2011-02-02.</ref>

Members of the ] are exposed to CS during initial training, and during training refresher courses or equipment maintenance exercises, using CS tablets that are melted on a hotplate. This is to demonstrate the importance of properly wearing a ] or ], as the agent's presence quickly reveals an improper fit or seal of the mask's rubber gaskets against the face. Following exposure while wearing a mask, recruits are ordered to remove the masks and endure exposure in the room for one minute. These exercises also encourage confidence in the ability of the equipment to protect the wearer from such chemical attacks. Such an event is a requirement for graduation from ], ], Navy Basic Training, and ].<ref> '']'' 2007. Retrieved on October 13, 2008</ref> CS gas in the form of grenades is also used extensively in the ] in some service schools. CS gas is used during the final field exercise of the Scout Sniper Basic Course to simulate being compromised. In addition, it is used during the {{convert|25|km|mi|adj=on|abbr=on}} escape-and-evasion exercise ("Trail of Tears"), the last event before graduation from the course. It is also used during several events in the ] (BRC) including some rucksack runs and escape-and-evasion exercises. While students going through the course are given the opportunity to bring and wear a gas mask for the event, usually none are worn because once donned, gas masks could not be removed until the end of the exercise. This could last anywhere from 3–12 hours and would make running 25&nbsp;km while wearing {{convert|125|lb|kg|abbr=on}} of gear virtually impossible.

===Vietnam===
It has been reported that thousands of tons of CS gas were used by the U.S. forces in ] to bring ] into the open. It was also used by the North Vietnamese forces in some battles like Hue in 1968 or during the Easter Offensive in 1972.<ref name="BryceR">Bryce, Robert. "." ''].'' July 7, 2000. Retrieved on September 23, 2007</ref>

===Elsewhere===
].]]

CS gas has been and is still routinely used by ] (MAT) in order to quell student and labor protests, as well as riots by hooligans. In some cases gas had expired for more than thirty years. The legality and safety of the use of CS by policemen has been challenged both by people within Greece and the European Union.{{Citation needed|date=June 2011}}

CS was used to quell a protest in ], ] in July 1997 and the 1999 WTO riots in Seattle. ] reported that it had been manufactured by the UK company Pains-Wessex. Subsequently, Amnesty called for an export ban when the receiving regime is either not fully trained in the use of CS, or had shown usage "contrary to the manufacturer’s instructions".<ref name=Amnesty>"."''].'' Retrieved on September 23, 2007</ref>

In September 2000, the ''Guardian'' newspaper revealed how a UK company, HPP, used legal loopholes to export CS to a private security company in ], in breach of ] sanctions.<ref name="GuardianHPP">Burke, Jason; Johnson-Thomas, Brian. "." '']''. September 10, 2000. Retrieved on September 23, 2007</ref> The ''Guardian'' also reported that CS was used by the ] militia in Rwanda to flush ]s out of buildings before hacking them to death.

CS has been used by the government in ]; by ] against ] and Israelis; by the ]n government in ], and during the ] conflicts by ]. In Malta it was used by Police between 1981 and 1987 to the detriment of Nationalist Party Supporters.

CS tear gas was used at the G8 protests in ], ]<ref name="Indy">Tartarini, Laura. "." ''.'' April 13, 2003. Retrieved on September 23, 2007</ref> and ], ]<ref name="Quebec">Di Matteo, Enzo. "." ''.'' May 177–23, 2001. Retrieved on September 23, 2007</ref> during the ] anti-globalization demonstrations during the ].

The Canadian, Norwegian and Australian Armies train their soldiers with CS gas in a manner similar to that of the USA, as it is a basic part of CBRN (Chemical, Biological, Radiological, Nuclear) training. Gas is released by burning tablets, usually in a building reserved for this purpose (a "gas hut"). In the training, the person enters the building unprotected, and must fit and clear the gas mask before leaving. Other drills such as drinking and under-mask decontamination are also practiced. Some Norwegian units are exposed to CS-gas while engaged in physical activity such as push-ups.

<!-- It has been widely reported that the Iranian government has used CS gas, and a mixture of concentrated CS gas and water thrown from helicopters, against protesters in Tehran during the ].

In Chile, from years of the Pinochet dictatorship, CS has been commonly used by Chilean police to dissolve any multitudinary acts, including riots in football stadiums and pacific political and environmental acts. On May 17, 2011, the use of CS was banned by the Chilean government but three days after, CS was re-introduced to confront environmental demonstrations against the HydroAysen project, which attempt installing a hydropower plant in the Chilean Patagonia.-->

==See also==
{{Portal|Pharmacy and Pharmacology}}
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==References==
{{Reflist|2}}

==External links==
* ]
* General Facts About Tear Agent O-Chlorobenzylidene Malononitrile (CS) {pdf}
* A Paper prepared by the Steering Group led by the Northern Ireland Office – April 2001
* statement on 2-chlorobenzylidene malononitrile (CS) and CS spray, September 1999. (pdf)
* Noxious Tear-Gas Bomb Mightier in Peace than in War.
* – The Omega Foundation (pdf)
* University of Nottingham paper on CS use in the UK.
*
*
*
*{{cite journal|author=Carron P-N, Yersin B|title=Management of the effects of exposure to tear gas|year=2009|volume=338|issue=7710|pages=1554–1558|doi=10.1136/bmj.b2283|journal=BMJ}}

{{Chemical warfare}}


{{chemical warfare}}
{{Transient receptor potential channel modulators}}
{{Good article}} {{Good article}}


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