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CR gas
CR gas
or dibenzoxazepine (also referred to as DBO), or its chemical name dibenz[b,f][1,4]oxazepine, is an incapacitating agent and a lachrymatory agent. CR was developed by the British Ministry of Defence as a riot control agent in the late 1950s and early 1960s. A report from the Porton Down
Porton Down
laboratories described exposure as "like being thrown blindfolded into a bed of stinging nettles", and it earned the nickname "firegas".[1][2]

Contents

1 Physical properties and deployment 2 Effects 3 Treatment 4 Use

4.1 Northern Ireland 4.2 Egypt 4.3 Philippines 4.4 Sri Lanka 4.5 Turkey 4.6 Ukraine 4.7 Vietnam 4.8 Elsewhere

5 See also 6 References

Physical properties and deployment[edit] CR is a pale yellow crystalline solid with a pepper-like odor. It is slightly soluble in water and does not degrade in it. CR is usually presented as a microparticulate solid, in the form of suspension in a propylene glycol-based liquid. Contrary to its common name, it is not a gas but a solid at room temperature. The dibenz[b,f][1,4]oxazepine moiety is present in the typical antipsychotic drug loxapine, but, unlike CR, loxapine is not reactive and is not an irritant. CR was first synthesised in 1962.[3] CR can be delivered either as an aerosol or a solution in water, making it able to be used in water cannons, smoke grenades, or handheld spray cans. For smoke it is usually fired in canisters (LACR) that heat up, producing an aerosol cloud at a steady rate. Effects[edit] CR gas
CR gas
is a lachrymatory agent (LA), exerting its effects through activation of the TRPA1
TRPA1
channel.[4] Its effects are approximately 6 to 10 times more powerful than those of CS gas. CR causes intense skin irritation, in particular around moist areas; blepharospasm, causing temporary blindness; and coughing, gasping for breath, and panic. It is capable of causing immediate incapacitation. It is a suspected carcinogen. It is toxic, but less so than CS gas, by ingestion and exposure. However, it can be lethal in large quantities. In a poorly ventilated space, an individual may inhale a lethal dose within minutes. Death is caused by asphyxiation and pulmonary edema. The effect of CR is long-term and persistent. CR can persist on surfaces, especially porous ones, for up to 60 days. Treatment[edit] While CS can be decontaminated with a large amount of water, use of water may exacerbate the effects of CR. Skin contaminated with CR gas may become extremely painful in contact with water for up to 48 hours after contamination.[3] Medical treatment is mostly palliative. The contaminated clothing has to be removed. The eyes and skin can be washed, the eye pain can be alleviated with medications.[5] Use[edit] Northern Ireland[edit] It started being available in police and army supplies, as a water cannon additive and as spray cans, in 1973 and was at least still so in 1981.[1][2] Republican groups in Northern Ireland have alleged that British Army and Royal Ulster Constabulary units used CR gas
CR gas
against Republican prisoners in the 1970s.[6] Additionally, there are British military documents now declassified and in the public domain held in the records of the UK Ministry of Defence at the National Archives, London, that suggest that the British Army did deploy and use CR gas in Northern Ireland. [7] [8] [9] [10] [11] Egypt[edit] During the 2011 protests against the military government in Egypt, Egyptian security forces allegedly used CR gas
CR gas
in addition to the more commonly used, less debilitating CS gas. One protester described the gas as making him feel "as if your eyes are about to fall out; then you have trouble breathing, and you lose your sight". Egyptians used yeast as a treatment for CR side effects on skin. Mohammed ElBaradei also confirmed via Twitter that "tear gas with [a] nerve agent" is being used in Tahrir Square.[12] The only gas that has been identified by human rights organizations in protests "is CS tear gas, typically used by police forces to disperse crowds," stated Egyptian journalist Farida Helmy.[13] Egyptian use of CR gas
CR gas
has not been corroborated according to Human Rights Watch (HRW). Philippines[edit] CR 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 of Sri Lanka, an insurgent group in Sri Lanka used CR gas
CR gas
against government forces that were on an offensive to flush and defeat these insurgents during September 2008. 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 CR gas
CR gas
as an insurgent weapon.[citation needed] Turkey[edit] In the June 2013 protest against the Turkish government, Turkish police allegedly used CR gas
CR gas
on protesters in Istanbul. Doctors in a makeshift first aid post in a Mosque judged it as such.[14][15] Ukraine[edit] In Ukraine, CR gas
CR gas
is commonly used by special forces against demonstrators. Gas is packed in a form of spray cans "Cobra 1". For example, gas has been used on demonstration dedicated to Ukraine Independence Day (Aug 24 2011).[16] Also massive gas usage has been documented during demonstrations against Language Law Draft at Kiev on Jul 3-4 2012.[17] Vietnam[edit] It has been reported that thousands of tons of CR gas
CR gas
were used by the U.S. forces in Vietnam to bring Viet Cong 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.[citation needed] Elsewhere[edit] In the late 1980s, CR was used in the townships in South Africa. It caused some fatalities, in particular among children.[18][19] Because of its alleged carcinogenic properties, the United States does not utilize CR for riot control.[20] The U.S. military classification for this chemical agent is combat class chemical weapon causing serious side-effects for humans. See also[edit]

CS gas Oxazepine Pepper spray Tear gas

References[edit]

^ a b Rosenhead, Jonathon (23 Jul 1981). "The technology of riot control". New Scientist.  ^ a b Wright, Steve (6 January 1998). "AN APPRAISAL OF TECHNOLOGIES OF POLITICAL CONTROL". The STOA Programme, Directorate General for Research, European Parliament. Retrieved 3 October 2015 – via pitt.edu.  ^ a b Higginbo R, Suschitzky H (1962). "Synthesis of Heterocyclic Compounds. 2. Cyclisation of O-Nitrophenyl Oxygen Ethers". J. Chem. Soc.: 2367–2370. doi:10.1039/jr9620002367.  ^ Gijsen HJ, Berthelot D, Zaja M, Brône B, Geuens I, Mercken M (October 2010). "Analogues of Morphanthridine and the Tear Gas Dibenz[b,f][1,4]oxazepine (CR) as Extremely Potent Activators of the Human Transient Receptor Potential Ankyrin 1 (TRPA1) Channel". J Med Chem. 53 (19): 7011–7020. doi:10.1021/jm100477n. PMID 20806939.  ^ "Tear Gases: CR - Dibenzoxazepine". Zarc International, Inc. Retrieved November 22, 2011.  ^ inac.org Archived May 16, 2008, at the Wayback Machine. ^ TNA DEFE 13/1379   "Northern Ireland: use of tear gases; use of CR gas
CR gas
for riot control in Northern Ireland, especially at HM Prison Maze; use of SPAD (Self Protection Aid Device) as a means of    delivery. 1973."   ^ TNA DEFE 24/967     "Northern Ireland: dibenzoxazepine (CR) gas; chemical agent for use in riot control. 1974-77."   ^ TNA DEFE 24/1090   "Northern Ireland: use of CS and CR gas
CR gas
in countering riots. 1969-77."   ^ TNA DEFE 24/1203   "Northern Ireland: terrorism; Operation PAGODA; use of CR gas
CR gas
(dibenzoxazepine). 1973-77."   This document is still classified, although a record of it is listed in the National    Archives (TNA) catalogue. ^ TNA DEFE 24/1903   "Development of CR gas: introduction of Self Protection Aid Devices (SPAD) in Northern Ireland; includes arguments for and against their use. 1971-73."   ^ "Beskylder egyptiske styrker for massakre" (in Norwegian). NRK.no. Retrieved November 22, 2011.  ^ Farida Helmy, "Chemical Combat", Egypt Today Magazine, January 2012 issue ^ 2013-06-05. "Erdogan's Police May Be Using Chemical CR Gas on Protesters". The Jewish Press. Retrieved 2013-09-02.  ^ ahmet hasan (3 June 2013). "Dolmabahçe Camii 03.06.2013 00:20" – via YouTube.  ^ "Керівництву МВС показали, якими «засобами гігієни» воно озброює «Беркут» - Новини - Український тиждень, Тиждень.ua".  ^ ""Беркут" відступив від Українського дому".  ^ Olajos EJ, Salem H (2001). "Riot Control Agents: Pharmacology, Toxicology, Biochemistry and Chemistry". J Appl Toxicol. 21 (5): 355–391. doi:10.1002/jat.767. PMID 11746179.  ^ "Ireland, Organise! Press Release -Less Lethal Weapons Action Belfast". A-Infos. Retrieved November 22, 2011.  ^ [1][dead link]

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 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

.