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5-chloro-2-quinolinecarbonitrile 6-chloro-2-quinolinecarbonitrile 7-chloro-2-quinolinecarbonitrile

Supplementary data page

Structure and properties

Refractive index
Refractive index
(n), Dielectric constant
Dielectric constant
(εr), etc.

Thermodynamic data

Phase behaviour solid–liquid–gas

Spectral data

UV, IR, NMR, MS

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

The compound 2-chlorobenzalmalononitrile (also called o-chlorobenzylidene malononitrile; chemical formula: C10H5ClN2), a cyanocarbon, is the defining component of a tear gas commonly referred to as CS gas, which is used as a riot control agent. 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 nose, mouth and throat mucous membranes causing profuse coughing, mucous nasal discharge, disorientation, and difficulty breathing, partially incapacitating the subject. CS gas
CS gas
is an aerosol of a volatile solvent (a substance that dissolves other active substances and that easily evaporates) and 2-chlorobenzalmalononitrile, which is a solid compound at room temperature. CS gas
CS gas
is generally accepted as being non-lethal. It was first synthesized by two Americans, Ben Corson and Roger Stoughton,[6] at Middlebury College
Middlebury College
in 1928, and the chemical's name is derived from the first letters of the scientists' surnames.[7][8] CS was developed and tested secretly at Porton Down
Porton Down
in Wiltshire, England, in the 1950s and 1960s. CS was used first on animals, then subsequently on British Army
British Army
servicemen volunteers. CS has less effect on animals due to "under-developed tear-ducts and protection by fur".[9]

Contents

1 Production

1.1 Use as an aerosol

2 Effects

2.1 Secondary effects

3 Toxicity 4 Decontamination

4.1 In the field 4.2 In a medical facility

4.2.1 When washing the clothing

5 Use

5.1 Bahrain 5.2 Canada 5.3 Chile 5.4 Cyprus 5.5 Egypt 5.6 Hong Kong 5.7 Iraq 5.8 Israel 5.9 Philippines 5.10 Sri Lanka 5.11 United Kingdom

5.11.1 Northern Ireland 5.11.2 Great Britain

5.11.2.1 CS gas 5.11.2.2 CS spray

5.12 United States 5.13 Vietnam 5.14 Elsewhere

6 See also 7 References 8 External links

Production[edit] CS is synthesized by the reaction of 2-chlorobenzaldehyde and malononitrile via the Knoevenagel condensation:

Preparation of CS

ClC6H4CHO + H2C(CN)2 → ClC6H4CHC(CN)2 + H2O

The reaction is catalysed with weak base like piperidine or pyridine. The production method has not changed since the substance was discovered by Corson and Stoughton.[10] Other bases, solvent free methods and microwave promotion have been suggested to improve the production of the substance.[11] 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."[10] Use as an aerosol[edit] As 2-chlorobenzalmalononitrile is a solid at room temperature, not a gas, a variety of techniques have been used to make this solid usable as an aerosol:

Melted and sprayed in the molten form. Dissolved in organic solvent. CS2 dry powder (CS2 is a siliconized, micro-pulverized form of CS). CS from thermal grenades by generation of hot gases.[2]

In the Waco Siege
Waco Siege
in the United States, CS was dissolved in the organic solvent dichloromethane (also known as methylene chloride). The solution was dispersed as an aerosol via explosive force and when the highly volatile dichloromethane evaporated, CS crystals precipitated and formed a fine dispersion in the air.[2] Effects[edit]

CS Gas
Gas
used on 1 May 2013 in Istanbul

Tear gas
Tear gas
shells used in Istanbul in 2013

CS gas
CS gas
shells used in Taksim Gezi Park, Istanbul, May 2013

Many types of tear gas and other riot control agents have been produced with effects ranging from mild tearing of the eyes to immediate vomiting and prostration. CN and CS are the most widely used and known, but around 15 different types of tear gas have been developed worldwide, e.g. adamsite or bromoacetone, 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 aerosol. The size of solution droplets and the size of the CS particulates after evaporation are factors determining its effect on the human body.[12] 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 and/or sunburned. In highly concentrated doses, it can also induce severe coughing and vomiting. Almost all of the immediate effects wear off within an hour (such as exceptional nasal discharge and profuse coughing), although the feeling of burning and highly irritated skin may persist for hours. Affected clothing will need to be washed several times or thrown away. Secondary effects[edit] People or objects contaminated with CS gas
CS gas
can cause secondary exposure to others, including healthcare professionals and police. In addition, repeated exposure may cause sensitisation.[13] Toxicity[edit] Although described as a non-lethal weapon for crowd control, studies have raised doubts about this classification. CS can cause severe pulmonary damage and can also significantly damage the heart and liver.[14] On 28 September 2000, Prof. Dr. Uwe Heinrich released a study commissioned by John C. Danforth, of the United States Office of Special
Special
Counsel, to investigate the use of CS by the FBI at the Branch Davidians' 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".[2] At least one study has associated CS exposure with miscarriages.[14] This is consistent with its reported clastogenic effect (abnormal chromosome change) on mammalian cells. In Israel, CS gas
CS gas
was reported to be the cause of death of Jawaher Abu Rahmah on 31 December 2010;[15] other reports suggest that he was killed by the impact of a high-velocity CS gas
CS gas
canister to the chest.[16] In Egypt, CS gas
CS gas
was reported to be the cause of death of several protesters in Mohamed Mahmoud Street near Tahrir square during the November 2011 protests. The solvent in which CS is dissolved, methyl isobutyl ketone (MIBK), is classified as harmful by inhalation; irritating to the eyes and respiratory system; and repeated exposure may cause skin dryness or cracking.[17] Decontamination[edit] Note: Anyone aiding a victim of CS gas
CS gas
exposure will also suffer similar severe irritation (unless goggles, gas masks, and impermeable gloves are worn). In the field[edit] Source:[18]

Move to fresh air. If the wind is blowing, face the wind. Flap your arms and rub your hair in a breeze; do not rub your eyes, nose, or skin. Eyes must be wide open using eye muscles (not fingers). Irrigate the eyes with large amounts of any of the following:

A solution of 1% sodium bicarbonate and water A saline solution consisting of one-half teaspoon (2.5 cc) salt per a quart (liter) of water Clean cool water

Remove clothing as soon as practical. This clothing should not be mixed with other clothing when washing. Shower, washing hair first using Borax, Ivory, or Lava soap. Bend over so that CS Gas
Gas
particles fall from head to ground. Then shower affected skin areas. No oils, creams or salves should be used.

In a medical facility[edit] Source:[19]

Move the patient to a well-ventilated area. Remove patient's clothing and dispose of all clothing in an air-tight container. The patient must be thoroughly showered with soap and water. The eyes should be copiously irrigated with physiological saline or water and examined for corneal abrasions. Patients in respiratory distress should be observed for bronchospasm and secondary pneumonia. In patients with pre-existing respiratory disease, suffering from acute bronchospasm: humidified oxygen, aminophylline, and inhaled sympathomimetics may be necessary.

Symptoms should subside within 60 minutes of exposure. When washing the clothing[edit] Clothing should be left outside overnight, exposed to air before being washed.:[18] Use a strong detergent. Clothes should be placed in a dryer equipped with a vent outside; take caution that the exhaust is away from pedestrians, especially children.:[18] Use[edit]

RWGŁ-3
RWGŁ-3
Polish tear gas grenade launcher.

CS was used during attempts to flush the Viet Cong
Viet Cong
from their tunnels in the Vietnam War.

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 who are trained in the use and application of CS spray are routinely exposed to it as part of their training.[citation needed] Blank pistol cartridges carrying CS in powder form have been released to the public. These, when fired at 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.[citation needed] Although predominantly used by police it has also been used in criminal attacks in various countries.[20][21][22][23] Use of CS in war is prohibited under the terms of the Chemical Weapons Convention, signed by most nations in 1993 with all but five other nations signing between 1994 and 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 nerve agents. Only four nations have not signed the Chemical Weapons Convention and are therefore unhindered by restrictions on the use of CS gas: Angola, Egypt, North Korea and Somalia.[24][25] Domestic police use of CS is legal in many countries, as the Chemical Weapons Convention prohibits only military use. Bahrain[edit]

Bahrain riot police
Bahrain riot police
use tear gas on protesters in Manama
Manama
during 2011-2012 Bahraini uprising

CS gas
CS gas
was used extensively by Bahrain's police from the start of the Bahraini uprising.[26](p260) The Bahrain Independent Commission of Inquiry concluded that Bahrain's police used a disproportionate amount of CS gas
CS gas
when dispersing protests, and that in some situations, police fired CS gas
CS gas
into private homes in an "unnecessary and indiscriminate" manner.[26](p277) In one particular incident witnessed by Commission investigators, police fired "at least four tear gas canisters (each containing six projectiles) ... from a short range into the kitchen and living room of a home."[26](p261) According to opposition activists and families of the dead, ten individuals died as a result of CS gas
CS gas
between 25 March 2011 and 17 December 2011.[27][28][29][30][31][32][33][34][35][36] One allegedly died from the impact of the CS gas
CS gas
canister,[32] and the remainder are said to have died from the effects of inhaling the gas. The Bahrain Independent Commission of Inquiry received information that a further three deaths may have been attributable to the use of CS gas.[26](pp239–40,253) Of these three, one allegedly died from the impact of the canister, and two from the effects of inhaling the gas. Canada[edit] The Canadian Forces exposes BMQ (basic training) candidates to CS gas as part of gas mask training/drills. This training continues as people move along their career in the Canadian Forces. Many law enforcement agencies use CS gas
CS gas
as a riot control device. Since 2008, the SPVM police force in Montreal has increased its use of CS Gas
Gas
for crowd control, although Police
Police
policy is to only use it as a "last resort". Several incidents where protesters have been seriously injured by having CS gas
CS gas
fired at them from point-blank range have raised concerns about the methodology and training of Officers in the Montreal Riot Squad, particularly in relation to "Use of Force".[37] Chile[edit] Tear gas
Tear gas
is extensively used in Chile by the Carbineros, to disrupt civilian protests.[38] Cyprus[edit] CS was first tested in the field by the British army in Cyprus
Cyprus
in 1958. At this time it was known by the code name T792.[39] Egypt[edit] CS has been widely used by Egyptian Police/Military Forces from January 2011 onwards. Hong Kong[edit] The Police
Police
Tactical Unit (Hong Kong) of the Hong Kong Police
Police
Force used 87 rounds of CS projectiles (both riot gun launched and hand thrown) in Hong Kong on September 28, 2014 against hundreds of unarmed demonstrators demanding democratic elections during 2014 Hong Kong protests, also known as the Umbrella Movement. The CS gas
CS gas
canisters and content used were purchased by the Hong Kong SAR Government from CHEMRING, a British weapons manufacturer. The crowd used umbrellas to fend off the gas, often ineffectively. Apart from the HK police, CS gas
CS gas
spray is also used by Witness Protection and Firearms Section of Independent Commission Against Corruption (Hong Kong) Iraq[edit] Iraq successfully developed CS during the 1970s and during the 1980s produced tons of the substance firstly at Salman Pak
Salman Pak
and later at al-Muthanna.[40] Blackwater Worldwide, acting as an agent of the United States, deployed CS in the Iraq War
Iraq War
from a helicopter hovering over a checkpoint in the Green Zone
Green Zone
in Baghdad.[41] Israel[edit] Israel
Israel
Police
Police
forces spray CS gas
CS gas
in riot control situations. It is widely used at demonstrations within the Palestinian Territories
Palestinian Territories
and at the Israeli West Bank barrier.[42][43] Philippines[edit] CS tear gas was used in suppression of the mutiny in Makati that was led by Sen. Antonio Trillanes. The tear gas was fired in the building and all the people in the building including reporters were affected.[citation needed] Sri Lanka[edit] The LTTE, also known as Tamil Tigers
Tamil Tigers
of Sri Lanka, an insurgent group in Sri Lanka
Sri Lanka
used CS gas
CS gas
against government forces in September 2008.[44] Its use hindered the army's progress but ultimately proved ineffective in preventing the army from overrunning LTTE
LTTE
positions. This is one of the few cases of insurgents using CS gas. United Kingdom[edit] Northern Ireland[edit] CS gas
CS gas
was used extensively in the Bogside
Bogside
area of Derry, Northern Ireland during the "Battle of the Bogside", a two-day riot in August 1969. A total of 1,091 canisters containing 12.5g of CS each, and 14 canisters containing 50 g of CS each, were released in the densely populated residential area.[45] On 30 August the Himsworth Inquiry 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 Belfast, the following year, known as the Falls Curfew, the Army fired up to 1,600 canisters into the densely populated Falls Road area. It was also used in Lenadoon
Lenadoon
on 9 July 1972 on the breakdown of the IRA ceasefire. Not long after, the British Army
British Army
and RUC ceased using CS in Northern Ireland. Great Britain[edit] CS gas[edit] CS gas
CS gas
has not been routinely deployed on the British mainland. It has seen use in rare cases.[46] The first use of CS gas
CS gas
on the UK mainland that was not part of military training was carried out in 1944 during a hostage siege at a north London
London
address. Soldiers were asked to throw CS grenades through the skylight in hope of bringing the incident to a speedy conclusion, but the hostage-taker had brought his civilian-issue gas mask with him, negating the effect.[citation needed] The siege of Trough Gate 1973 in Oldham
Oldham
was the second non-military use of CS gas
CS gas
on the UK mainland. During a four-hour standoff, Frank Alan Stockton shot at police but was flushed from his home with CS gas and police dogs.[47][48][49] During the 1980 assault on the Iranian Embassy, SAS soldiers used CS gas (that was contained within Stun Grenades) to incapacitate the hostiles who had kept the building under siege for six days. All the remaining hostages were saved and all but one of the hostiles were eliminated, with the other being taken into custody.[50] In 1981, CS gas
CS gas
was used to quell rioting in the Toxteth
Toxteth
area of Liverpool.[51][52] In the March 2007 shootings in Leicester, CS gas
CS gas
was used after which a scuffle broke out. On 11 March 2007 a shooting incident occurred at around 2.45am following a performance by Pretty Ricky at the university. A 21-year-old student at the university, who was employed as security staff at the event, received gunshot wounds to his abdomen and was taken to hospital where his condition was not believed to be life-threatening. Six others were also injured during what was described as a scuffle that broke out after CS gas
CS gas
(tear gas) was sprayed following the event. Following the 2011 England riots, there was consideration given to making CS gas, water cannon and other riot control measures available to police for use in the event of serious disorder.[53] The British Armed Forces
British Armed Forces
use CS gas
CS gas
annually to test their CBRN equipment. During initial training they introduce recruits to CS gas by placing them in a small enclosed space known as a Respirator Testing Facility (RTF) and igniting chemical tablets to induce CS production. After recruits have carried out their CBRN
CBRN
drills, they must remove their respirators so that they are exposed to the CS for up to 20 seconds to experience its effects and become confident their respirators work.[54] CS spray[edit] CS incapacitant spray has been used routinely by the British police since its introduction in 1996. It is issued as an item of equipment to police officers for protection and to assist in dealing with violent incidents.[46][55] A six-month trial by sixteen police forces in England began on 1 March 1996. On 16 March 1996, a Gambian asylum seeker, Ibrahima Sey, was taken to Ilford
Ilford
Police
Police
Station in east London. Whilst incapacitating Sey, who was suffering from excited delirium, police sprayed him with CS spray and held him on the ground for approximately 15 minutes, and he subsequently died.[56] In 1999, the mental health charity MIND called for a suspension of the use of CS spray on mentally ill people until it was proved to be safe.[57] The CS spray used by police forces is in the form of a hand-held aerosol canister containing a 5% solution of CS dissolved in methyl isobutyl ketone and propelled by pressurized nitrogen.[58] The CS spray used by UK police is generally more concentrated than that used by American police forces (5% vs 1%).[59] The liquid stream is directed where the user points the canister, being accurate up to 4 metres. Police
Police
are also trained in helping the incapacitated person recover once successfully restrained.[58] Under UK firearm law, CS and other incapacitant sprays are classed as prohibited weapons, making it unlawful for a member of the public to possess them.[60] Some forces have opted to replace CS spray with Captor or PAVA spray,[61][62] with 60% of forces now estimated to be using PAVA.[63] In February 2006, Dan Ford, from Wareham in Dorset, received permanent scarring to his face after being sprayed with CS during an arrest by police. 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."[64] To give an indication as to the frequency of use of CS sprays by police, officers in Reading, Berkshire
Reading, Berkshire
deployed personal incapacitant spray on 486 occasions over a two-and-a-half year period from April 2009.[65] CS spray was used in the UK more than 10,000 times in the period between its introduction in 1996 and September 1998.[66] United States[edit] CS is used by many police forces within the United States. It was used by Federal Bureau of Investigation
Federal Bureau of Investigation
law enforcement officials in the 1993 Waco Siege.[67] Riot police in Pittsburgh, Pennsylvania in September 2009 used CS gas and riot control techniques to disperse assemblies in the vicinity of the 2009 G-20 Pittsburgh
Pittsburgh
summit. In Berkeley, California during the Bloody Thursday events in the People's Park on 21 May 1969, a midday memorial was held for student James Rector, a non-protester shot and killed by police, at Sproul Plaza on the University campus. In his honor, several thousand people peacefully assembled to listen to speakers remembering his life. 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.[68][69] Members of the United States armed forces
United States armed forces
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 gas or protective mask, 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. 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 United States Army Basic Training, Air Force Basic Military Training, Navy Basic Training, and Marine Corps recruit training.[70] CS gas
CS gas
in the form of grenades is also used extensively in the United States Marine Corps and United States Army 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 25 km (16 mi) escape-and-evasion exercise ("Trail of Tears"), the last event before graduation from the course. It is also used during several events in the Marine Corps Basic Reconnaissance Course (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 km while wearing 125 lb (57 kg) of gear virtually impossible. Vietnam[edit] It has been reported that thousands of tons of CS gas
CS gas
were used by the U.S. forces in Vietnam to bring Viet Cong
Viet Cong
into the open.[citation needed] It was also used by the North Vietnamese forces in some battles like Hue in 1968 or during the Easter Offensive in 1972.[71][not in citation given] Elsewhere[edit]

Police
Police
fire tear gas at protesters in Quebec.

CS gas
CS gas
has been and is still routinely used by Greek riot police
Greek riot police
(MAT) in order to quell student and labour protests, as well as riots. CS was used to quell a protest in Lusaka, Zambia in July 1997 and the 1999 WTO riots in Seattle. Amnesty International
Amnesty International
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".[72] In September 2000, the Guardian newspaper revealed how a UK company, HPP, used legal loopholes to export CS to a private security company in Rwanda, in breach of United Nations
United Nations
sanctions.[73] The Guardian also reported that CS was used by the Hutu
Hutu
militia in Rwanda
Rwanda
to flush Tutsis out of buildings before hacking them to death. CS has been used by the government in South Africa; by Israel
Israel
against Palestinians
Palestinians
and Israelis; by the South Korean government in Seoul, and during the Balkan
Balkan
conflicts by Serbia. 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 Genoa, Italy[74] and Quebec City, Canada[75] during the FTAA
FTAA
anti-globalization demonstrations during the Quebec City
Quebec City
Summit of the Americas. The Malaysia
Malaysia
Federal Reserve Unit
Federal Reserve Unit
has also been known to use CS tear gas against its citizens who rallied for clean and fair elections under what were called Bersih
Bersih
rallies in 2011[76] and 2012.[77] The Canadian, Norwegian and Australian Defence Forces train their personnel with CS gas
CS gas
in a manner similar to that of the USA, as it is a basic part of CBRN
CBRN
(Chemical, Biological, Radiological, Nuclear) training. Gas
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 practised. Some Norwegian units are exposed to CS gas
CS gas
while engaged in mental and physical activity such as addressing the officer in command by stating name, rank and troop before doing 30 push-ups.[78] France
France
repeatedly used CS gas
CS gas
against refugees in camps around Calais in 2015.[79] In Australia, prison officers used CS gas
CS gas
against five teenage boys in Darwin's Don Dale Juvenile Detention Centre in August 2014.[80] See also[edit]

Pharmacy and Pharmacology portal

List of parties to the Chemical Weapons Convention CR gas CN gas Pepper spray Chemical Weapons Convention Hand grenades

References[edit]

^ Williams, Kenneth E. "Detailed Facts About Tear Agent O-Chlorobenzylidene Malononitrile
Malononitrile
(CS) Archived 26 September 2007 at the Wayback Machine.". U.S. Army Center for Health Promotion and Preventive Medicine. Retrieved on 23 September 2007. ^ a b c d Heinrich, U. "Possible lethal effects of CS tear gas on Branch Davidians
Branch Davidians
during the FBI raid on the Mount Carmel compound near Waco, Texas." www.veritagiustizia.it. September 2000. Retrieved on 23 September 2007 ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0122". National Institute for Occupational Safety and Health (NIOSH).  ^ Hoenig, Steven L. (2006). Compendium of Chemical Warfare Agents. Springer. p. 138. ISBN 0-387-34626-0.  ^ "o-Chlorobenzylidene malononitrile". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).  ^ Corson, Ben B.; Stoughton, Roger W. (1928). "Reactions of Alpha, Beta-Unsaturated Dinitriles". Journal of the American Chemical Society. 50 (10): 2825–2837. doi:10.1021/ja01397a037.  ^ "CS". Oxford English Dictionary
Oxford English Dictionary
(3rd ed.). Oxford University Press. September 2005.  (Subscription or UK public library membership required.) ^ "CS, chemical compound". columbia.thefreedictionary.com. Retrieved on 23 September 2007. ^ "Orthochlorobenzylidenemalononitrile ClC6H4CHCCN(CN)2". Zarc International. Retrieved on 23 September 2007 ^ a b Corson BB, Stoughton RW (1928). "Reactions of Alpha, Betha-Unsaturated Dinitriles". J Am Chem Soc. 50 (10): 2825–2837. doi:10.1021/ja01397a037.  ^ Pande A, Ganesan K, Jain AK, Gupta PK, Malhotr RC (2005). "Novel Eco-Friendly Process for the Synthesis of 2-Chlorobenzylidenemalononitrile and ITS Analogues Using Water As a Solvent". Org Proc Res Develop. 9 (2): 133–136. doi:10.1021/op0498262.  ^ "Safer Restraint: A report of the conference held in April 2002 at Church House, Westminster." Police
Police
Complaints Authority. Retrieved on 23 September 2007 ^ Carron, P. N.; Yersin, B. (2009). "Management of the effects of exposure to tear gas". BMJ (Clinical research ed.). 338: b2283. doi:10.1136/bmj.b2283. PMID 19542106.  ^ a b Hu, H.; Cook-Deegan, R.; Shukri, A. (1989). "The use of chemical weapons. Conducting an investigation using survey epidemiology". JAMA: the Journal of the American Medical Association. 262 (5): 640–3. doi:10.1001/jama.1989.03430050056026. PMID 2746816.  ^ "Bil'in protester dies after exposure to tear gas shot by IDF". Haaretz. 31 December 2010.  ^ "Palestinian killed in Bilin protest". YNET news. 17 April 2009.  ^ "MSDS for 99% 4-Methyl-2-pentanone (MIBK)" (PDF). Alfa Aesar. Retrieved 7 January 2013.  ^ a b c "Decontamination Personal". www.cainstructor.com. Retrieved 2017-07-14.  ^ Bhattacharya, S. T.; Hayward, A. W. (1993). "CS gas?implications for the anaesthetist". Anaesthesia. 48 (10): 896–7. doi:10.1111/j.1365-2044.1993.tb07424.x. PMID 8238834.  ^ Kelso, Paul. " CS gas
CS gas
attack by former pupil injures 68 children." The Guardian. 1 October 1999. Retrieved on 23 September 2007 ^ Condon, Deborah. " Gas
Gas
attack at Dublin hospital." www.irishhealth.com. 14 May 2004. Retrieved on 23 September 2007 ^ "Shopkeeper attacked with CS gas." BBC News. 1 December 2005. Retrieved on 23 September 2007 ^ "Car thieves spray gas at motorist." BBC News. 4 January 2006. Retrieved on 23 September 2007 ^ United Nations
United Nations
Treaty Collection. Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction. Retrieved 19 January 2009. ^ Organisation for the Prohibition of Chemical Weapons. "States that nave neither signed nor acceded to the Chemical Weapons Convention". Retrieved 17. August 2014 ^ a b c d Report of the Bahrain Independent Commission of Inquiry (PDF) (Report). Bahrain Independent Commission of Inquiry. 23 November 2011.  ^ وفاة سبعيني في المعامير اختناقاً بغازات "الأمن" و "الداخلية" تنفي [Death of septuagenarian in Ma'ameer by suffocation from gas, Public Security and Ministry of Interior deny]. Alwasat (in Arabic). 26 March 2011. Retrieved 12 December 2011.  ^ "Bahrain group calls for boycott of Iranian goods". Associated Press. 30 April 2011. Retrieved 12 December 2011.  ^ "Bahrain police 'suppress protest'". Al Jazeera. 3 June 2011. Retrieved 12 December 2011.  ^ "Woman's death sparks new tension in Bahrain". Deutsche Presse-Agentur. 16 July 2011. Retrieved 12 December 2011.  ^ "Bahrain probes abuse after tear gas kills man". Reuters. 31 August 2011. Retrieved 12 December 2011.  ^ a b Goodman, J. David (2 August 2011). "A 14-Year-Old Boy Is Killed in Bahrain as Security Forces Break Up a Protest". The New York Times. Retrieved 12 December 2011.  ^ "Bahrain man dies after inhaling tear gas". Associated Press. 15 September 2011. Retrieved 12 December 2011.  ^ "عائلة لطف الله: وثقنا وفاة والدنا متأثراً ب "مسيلات الدموع [Family of Lutf Allah: we believe that our father's death was caused by tear gas]. Alwasat (in Arabic). 1 October 2011. Retrieved 12 December 2011.  ^ Kerr, Simeon (12 December 2011). "Baby's death threatens Bahrain reform agenda". Financial Times. Retrieved 12 December 2011.  ^ "Thousands demonstrate at funeral of Bahrain man". The Guardian. London. Associated Press. 18 December 2011.  ^ " Police
Police
stun grenade blamed for student's eye injury". CBC News. 8 March 2012.  ^ " Tear gas
Tear gas
used at Chile protest over education". aljazeera. 12 June 2014.  ^ "Final Report of the Expert Panel to Review SAS Veterans’ Health Concerns (Appendix D)." Retrieved on 23 September 2007 ^ "WMD Profiles: Chemical." Iraq Watch. Retrieved on 23 September 2007 ^ Risen, James (10 January 2008). "2005 Use of Gas
Gas
by Blackwater Leaves Questions". The New York Times. Retrieved 8 August 2009.  ^ "Four Palestinians
Palestinians
faint after inhaling CS gas". 8 August 2009.  ^ "Dozens hit by CS gas
CS gas
during anti-wall demonstrations". 22 August 2009.  ^ " LTTE
LTTE
used CS Gas
Gas
to attack Soldiers". Lanka Daily News. 18 September 2008. Retrieved 4 January 2011.  ^ McClean, Raymond (1997). The Road To Bloody Sunday (revised edition). Guildhall: Printing Press. ISBN 0-946451-37-0.  (extracts available online) ^ a b "British police face a CS gas
CS gas
attack". Guardian. London. 8 July 1999. Retrieved 6 January 2013.  ^ Ayala, Beatriz (29 July 2009). "Hero of Trough Gate siege dies at 72". Oldham
Oldham
Evening Chronicle.  ^ McPhee, Don. "Photo, The siege of Trough Gate Oldham
Oldham
1973". The Guardian. TopFoto. Retrieved 28 March 2013.  ^ McPhee, Don. "Photo, The siege of Trough Gate Oldham
Oldham
1973". The Guardian. TopFoto. Retrieved 28 March 2013.  ^ Knighton, Andrew (21 June 2017). "Operation Nimrod: The SAS Assault on the Iranian Embassy". War History Online.  ^ Kelly, Stephen (1 July 2011). "Toxteth's toxic legacy: Liverpool
Liverpool
is still feeling the impact of the Toxteth
Toxteth
riots". The Independent. London. Retrieved 6 January 2013.  ^ "On This Day: 20 May 1965: British police to be issued with tear gas." BBC News. Retrieved on 23 September 2007 ^ "UK police ponder using CS gas
CS gas
against rioters". Reuters. March 2012.  ^ "MoD confirms army CS gas
CS gas
investigation". Politics.co.uk. 13 May 2006. Retrieved 6 January 2013.  ^ Euripidou E, MacLehose R, Fletcher A (2004). "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)". Emerg Med J. 21 (5): 548–52. doi:10.1136/emj.2003.012773. PMC 1726417 . PMID 15333526.  ^ "Report on the death of Ibrahima Sey." Inquest. 1997 ^ "Experts fear unknown CS spray risks." BBC News. 24 September 1999. Retrieved on 23 September 2007 ^ a b Guidance on the Use of Incapacitant Spray (PDF). Association of Chief Police
Police
Officers of England, Wales and Northern Ireland. 2009. p. 22. Archived from the original (PDF) on 9 March 2013.  ^ Southward RD (2000). "CS incapacitant spray". J Accid Emerg Med. 17 (1): 76. doi:10.1136/emj.17.1.76-a. PMC 1756282 . PMID 10659007.  ^ "Weapons subject to general prohibition". Firearms Act 1968. UK Government. Retrieved 6 January 2013.  ^ "'Chilli' spray to replace CS gas". BBC News. 27 June 2005. Retrieved 6 January 2013.  ^ "'Safer' Pava to replace CS spray". BBC News. 22 January 2008. Retrieved 6 January 2013.  ^ "CAPTOR 2 P.A.V.A." Civil Defence Supply Ltd. Retrieved 6 January 2013.  ^ "CS spray man 'scarred for life'." BBC News. 2 February 2006. Retrieved on 23 September 2007 ^ Pyle, Mike (11 October 2011). "Captor spray used 500 times by police in two years". getreading. Retrieved 7 January 2013.  ^ "Safety fears prompt CS spray review". BBC News. 24 September 1998. Retrieved 6 January 2013.  ^ "A Primer on CS Gas." Public Broadcasting Service. 1995. Retrieved on 23 September 2007 ^ Nation: Occupied Berkeley. TIME (30 May 1969). Retrieved on 2 February 2011. ^ The Sixties and Seventies from Berkeley to Woodstock. Fsmitha.com. Retrieved on 2 February 2011. ^ TRADOC Regulation 350-6 TRADOC 2007. Retrieved on 13 October 2008 ^ Bryce, Robert (7 July 2000). "Lethal Weapon: FBI's Use of Tear Gas Questioned at Davidian Trial." The Austin Chronicle. Retrieved on 23 September 2007 ^ "Stopping the Torture Trade: 3 – Chemical Control."Amnesty International. Retrieved on 23 September 2007 ^ Burke, Jason; Johnson-Thomas, Brian. "British firms trade in torture." The Guardian. 10 September 2000. Retrieved on 23 September 2007 ^ Tartarini, Laura (13 April 2003). "Genova Update." italy.indymedia.org. Retrieved on 23 September 2007 ^ Di Matteo, Enzo (17 May 2001). "Foggy Over Tear Gas
Gas
Safety." NOW Online Edition. Retrieved on 23 September 2007 ^ " Malaysia
Malaysia
cracks down on protesters." Al Jazeera. 10 July 2011. Retrieved on 30 April 2012 ^ Shukry, Anisah (29 April 2012) "Probe violence against press, media groups urge Najib." The Malaysian Insider. Retrieved on 30 April 2012 ^ Military magazine detailing Norwegian recruit training – http://www.fofo.no/filestore/FNR12_2011.pdf ^ https://www.telegraph.co.uk/news/worldnews/europe/france/11884297/Migrants-tear-gassed-by-French-riot-police-at-Calais-Jungle-camp.html ^ [1]

External links[edit]

Wikimedia Commons has media related to CS gas.

Salem H, Gutting B, Kluchinsky T, Boardman C, Tuorinsky S, Hout J (2008). Medical Aspects of Chemical Warfare, Chapter 13 Riot Control Agents, US Army Medical Institute, Borden Institute, pp. 441–484 (2008). Carron P-N, Yersin B (2009). "Management of the effects of exposure to tear gas". BMJ. 338 (7710): 1554–1558. doi:10.1136/bmj.b2283. PMID 19542106.  Hout J, Hook G, LaPuma P, White D (2010). "Identification of compounds formed during low temperature thermal dispersion of encapsulated o-chlorobenzylidene malononitrile (CS riot control agent)" Journal of Occupational and Environmental Hygiene, June 2010 Hout, Joseph; Kluchinsky, Timothy; LaPuma, Peter; White, Duvel (2011). "Evaluation of CS (o-Chlorobenzylidene Malononitrile) Concentrations During U.S. Army Mask Confidence Training", Journal of Environmental Health, October 2011 Gas
Gas
Chromatography NIST (rehosted) U.S. Army Center for Health Promotion and Preventive Medicine General Facts About Tear Agent O-Chlorobenzylidene Malononitrile
Malononitrile
(CS) pdf CDC – NIOSH Pocket Guide to Chemical Hazards – o-Chlorobenzylidene malononitrile Patten report recommendations 69 and 70 relating to public order equipment A Paper prepared by the Steering Group led by the Northern Ireland Office – April 2001 Committees on toxicity, mutagenicity and carcinogenicity of chemicals in food, consumer products and the environment statement on 2-chlorobenzylidene malononitrile (CS) and CS spray, September 1999. (pdf) Journal of Non-lethal Combatives, January 2003 Noxious Tear- Gas
Gas
Bomb Mightier in Peace than in War. "Crowd Control Technologies: An Assessment Of Crowd Control Technology Options For The European Union" – The Omega Foundation (pdf) Health and safety in policing University of Nottingham paper on CS use in the UK. BBC 'wiki' site – entry on CS gas eMedicine Information on irritants: Cs, Cn, Cnc, Ca, Cr, Cnb, PS

v t e

Agents used in chemical warfare incapacitation riot control

Blood

Cyanogen Cyanogen
Cyanogen
bromide Cyanogen
Cyanogen
chloride (CK) Hydrogen cyanide
Hydrogen cyanide
(AC) Arsine Vinyl arsine

Blister

Ethyldichloroarsine
Ethyldichloroarsine
(ED) Methyldichloroarsine
Methyldichloroarsine
(MD) Phenyldichloroarsine
Phenyldichloroarsine
(PD) Lewisite
Lewisite
(L) Sulfur mustard
Sulfur mustard
(HD H HT HL HQ) Nitrogen
Nitrogen
mustard

HN1 HN2 HN3

Nerve

G-agents

Tabun (GA) Sarin
Sarin
(GB) Soman
Soman
(GD) Cyclosarin
Cyclosarin
(GF) GV

V-agents

EA-3148 VE VG VM VP VR VX

Novichok agents

A-234

Carbamates

EA-3990 EA-4056 T-1123

Neurotoxins

Saxitoxin
Saxitoxin
(TZ) Botulinum toxin
Botulinum toxin
(BTX) Tetanospasmin
Tetanospasmin
(TeNT) Ricin

Nettle

Phosgene oxime
Phosgene oxime
(CX)

Pulmonary/Choking agent

Chlorine Phosgene
Phosgene
(CG) Perfluoroisobutene Chloropicrin
Chloropicrin
(PS) Diphosgene
Diphosgene
(DP) Disulfur decafluoride Acrolein Ethyl bromoacetate

Vomiting agent

Adamsite Chloropicrin Diphenylchlorarsine Diphenylcyanoarsine Diphenylamincyanoarsine

Incapacitating

Agent 15 (BZ) Dimethylheptylpyran
Dimethylheptylpyran
(DMHP) EA-3167 Kolokol-1 LSD-25 PAVA spray Sleeping gas

Riot control

Xylyl bromide Pepper spray
Pepper spray
(OC) Mace (spray) CN CS CR

List of chemical warfare agents CB military symbol

v t e

TRP channel modulators

TRPA

Activators

4-Hydroxynonenal 4-Oxo-2-nonenal 4,5-EET 12S-HpETE 15-Deoxy-Δ12,14-prostaglandin J2 α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Acrolein Allicin
Allicin
(garlic) Allyl isothiocyanate
Allyl isothiocyanate
(mustard, radish, horseradish, wasabi) AM404 Bradykinin Cannabichromene
Cannabichromene
(cannabis) Cannabidiol
Cannabidiol
(cannabis) Cannabigerol
Cannabigerol
(cannabis) Cinnamaldehyde
Cinnamaldehyde
(cinnamon) CR gas
CR gas
(dibenzoxazepine; DBO) CS gas
CS gas
(2-chlorobenzal malononitrile) Curcumin
Curcumin
(turmeric) Dehydroligustilide (celery) Diallyl disulfide Dicentrine
Dicentrine
( Lindera
Lindera
spp.) Farnesyl thiosalicylic acid Formalin Gingerols (ginger) Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate Ligustilide (celery, Angelica acutiloba) Linalool
Linalool
(Sichuan pepper, thyme) Methylglyoxal Methyl salicylate
Methyl salicylate
(wintergreen) N-Methylmaleimide Nicotine
Nicotine
(tobacco) Oleocanthal
Oleocanthal
(olive oil) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) PF-4840154 Phenacyl chloride Polygodial
Polygodial
(Dorrigo pepper) Shogaols (ginger, Sichuan and melegueta peppers) Tear gases Tetrahydrocannabinol
Tetrahydrocannabinol
(cannabis) Thiopropanal S-oxide
Thiopropanal S-oxide
(onion) Umbellulone
Umbellulone
(Umbellularia californica) WIN 55,212-2

Blockers

Dehydroligustilide (celery) Nicotine
Nicotine
(tobacco) Ruthenium red

TRPC

Activators

Adhyperforin
Adhyperforin
(St John's wort) Diacyl glycerol GSK1702934A Hyperforin
Hyperforin
(St John's wort) Substance P

Blockers

DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid

TRPM

Activators

ADP-ribose BCTC Calcium
Calcium
(intracellular) Cold Coolact P Cooling Agent 10 CPS-369 Eucalyptol
Eucalyptol
(eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol
Menthol
(mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens) Steviol glycosides (e.g., stevioside) (Stevia rebaudiana) Sweet tastants (e.g., glucose, fructose, sucrose; indirectly) Thio-BCTC WS-3 WS-12 WS-23

Blockers

Capsazepine Clotrimazole DCDPC Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-amylcinnamoyl)anthranilic acid Nicotine
Nicotine
(tobacco) Niflumic acid Ruthenium red Rutamarin (Ruta graveolens) Tolfenamic acid TPPO

TRPML

Activators

MK6-83 PI(3,5)P2 SF-22

TRPP

Activators

Triptolide
Triptolide
(Tripterygium wilfordii)

Blockers

Ruthenium red

TRPV

Activators

2-APB 5',6'-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Allicin
Allicin
(garlic) AM404 Anandamide Bisandrographolide (Andrographis paniculata) Camphor
Camphor
(camphor laurel, rosemary, camphorweed, African blue basil, camphor basil) Cannabidiol
Cannabidiol
(cannabis) Cannabidivarin
Cannabidivarin
(cannabis) Capsaicin
Capsaicin
(chili pepper) Carvacrol
Carvacrol
(oregano, thyme, pepperwort, wild bergamot, others) DHEA Diacyl glycerol Dihydrocapsaicin
Dihydrocapsaicin
(chili pepper) Estradiol Eugenol
Eugenol
(basil, clove) Evodiamine
Evodiamine
(Euodia ruticarpa) Gingerols (ginger) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin
Homocapsaicin
(chili pepper) Homodihydrocapsaicin
Homodihydrocapsaicin
(chili pepper) Incensole
Incensole
(incense) Lysophosphatidic acid Low pH (acidic conditions) Menthol
Menthol
(mint) N-Arachidonoyl dopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide
Nonivamide
(PAVA) (PAVA spray) Nordihydrocapsaicin
Nordihydrocapsaicin
(chili pepper) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) Phorbol esters
Phorbol esters
(e.g., 4α-PDD) Piperine
Piperine
(black pepper, long pepper) Polygodial
Polygodial
(Dorrigo pepper) Probenecid Protons RhTx Rutamarin (Ruta graveolens) Resiniferatoxin
Resiniferatoxin
(RTX) (Euphorbia resinifera/pooissonii) Shogaols (ginger, Sichuan and melegueta peppers) Tetrahydrocannabivarin
Tetrahydrocannabivarin
(cannabis) Thymol
Thymol
(thyme, oregano) Tinyatoxin
Tinyatoxin
(Euphorbia resinifera/pooissonii) Tramadol Vanillin
Vanillin
(vanilla) Zucapsaicin

Blockers

α- Spinasterol
Spinasterol
( Vernonia
Vernonia
tweediana) AMG-517 Asivatrep BCTC Cannabigerol
Cannabigerol
(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol
Cannabinol
(cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047 Lanthanum Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid NGD-8243 Niflumic acid Pregnenolone sulfate RN-1734 RN-9893 Ruthenium red SB-705498 Tivanisiran Tolfenamic acid

See also: Receptor/signaling modulators • Ion channe

.