Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tabun (nerve agent): Difference between pages

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| ImageFile2 = Tabun.svg

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| IUPACName = (''RS'')-Ethyl ''N'',''N''-Dimethylphosphoramidocyanidate

| OtherNames = GA; Ethyl dimethylphosphoramidocyanidate; Dimethylaminoethoxy-cyanophosphine oxide; Dimethylamidoethoxyphosphoryl cyanide; Ethyl dimethylaminocyanophosphonate; Ethyl ester of dimethylphosphoroamidocyanidic acid; Ethyl phosphorodimethylamidocyanidate; Cyanodimethylaminoethoxyphosphine oxide; Dimethylaminoethodycyanophosphine oxide; EA-1205; TL-1578

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| ChEMBL = 1097650

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 77-81-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S45M750QSH

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| PubChem = 6500

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|Section2={{Chembox Properties

| C=5 | H=11 | N=2 | O=2 | P=1

| Density = 1.0887 g/cm³ at 25 °C<br />1.102 g/cm³ at 20 °C

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|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards = Highly toxic. Fires involving this chemical may result in the formation of [[hydrogen cyanide]]

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'''Tabun''' (military designation '''GA''') is an extremely toxic compound of the [[organophosphate]] family.<ref>{{Cite journal |date=2021-10-02 |title=CBRNE - Nerve Agents, G-series - Tabun, Sarin, Soman: Practice Essentials, Pathophysiology, Epidemiology |url=https://emedicine.medscape.com/article/831648-overview |journal=[[Medscape]]}}</ref><ref name=":0">{{Cite journal |date=2021-10-02 |title=CBRNE - Nerve Agents, G-series - Tabun, Sarin, Soman: Practice Essentials, Pathophysiology, Epidemiology |url=https://emedicine.medscape.com/article/831648-overview |journal=[[CBRNE]] |at=Pathophysiology |via=Medscape}}</ref> It is not present in nature. At room temperature, the pure compound presents itself as a clear and viscous liquid. However, impurities imparted during its manufacture are almost always present in some amount, turning it into a yellow or brown liquid. Exposed to environs, it slowly volatizes into the atmosphere,<ref>{{Cite web |title=NRT CBRN Tabun 2022 07 26.pdf |url=https://nrt.org/sites/2/files/NRT%20CBRN%20CHEM%20UPDATE%20Tabun%20GA%20QRG%20FINAL%202022%2007%2026.pdf |website=NRT.org}}</ref> with the vapor having a slight fruity or almond-like odor.<ref name=":1">{{Cite web |date=2024-04-26 |title=Tabun (GA): Nerve Agent {{!}} NIOSH {{!}} CDC |url=https://www.cdc.gov/niosh/ershdb/emergencyresponsecard_29750004.html |access-date=2024-07-26 |website=www.cdc.gov |language=en-us}}</ref> As the compound has a much higher [[molecular mass]] (162 g/mol) compared to air, Tabun gas tends to accumulate in low-lying areas.<ref name=":1" />

It is a potent inhibitor of a key [[enzyme]], [[acetylcholinesterase]], within the human body as well as in other animals.<ref>{{Cite web |last=PubChem |title=Tabun |url=https://pubchem.ncbi.nlm.nih.gov/compound/6500 |access-date=2024-07-26 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> It is responsible for breaking down [[acetylcholine]], a [[neurotransmitter]] released into the [[Chemical synapse|synaptic cleft]] by motor neurons. The presence of acetylcholine within the cleft signals the post-synaptic (downstream) motor neuron to contract the neuron's associated [[Muscle cell|muscle fibers]], and vice versa. By irreversibly [[Phosphorylation|phosphorylating]] the enzyme,<ref name=":0" /> Tabun accomplishes a constant and involuntary contraction of the affected muscles, as the acetylcholine is not recycled and continues to build up within the cleft. Death of the organism ensues when respiratory muscles, such as the [[Thoracic diaphragm|diaphragm]] and [[Internal intercostal muscles|intercostals]], become exhausted and paralyzed from constant contraction, leading to loss of respiratory functions.<ref name=":0" />

The production and storage of Tabun has been strictly regulated under the [[Chemical Weapons Convention]] and its implementing agency [[Organisation for the Prohibition of Chemical Weapons|OPCW]] since 1997.<ref>{{Cite web |title=Tabun - an overview {{!}} ScienceDirect Topics |url=https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/tabun |access-date=2024-07-26 |website=www.sciencedirect.com}}</ref> As a Schedule 1 Toxic Chemical,<ref>{{Cite web |title=Schedule 1 |url=https://www.opcw.org/chemical-weapons-convention/annexes/annex-chemicals/schedule-1 |access-date=2024-07-26 |website=OPCW |language=en}}</ref> the synthesis of more than 100 grams of the substance per year must be declared to the organization, and no signing nation can possess more than 1 ton of the chemical.<ref>{{Cite web |title=Chemical Weapons Convention - CWC_en.pdf |url=https://www.opcw.org/chemical-weapons-convention/download-convention |access-date=2024-07-26 |website=OPCW |page=4 |language=en}}</ref> Modern usage of Tabun is limited to research purposes in minute amounts.<ref>{{Cite web |title=Chemical Weapons Convention - CWC_en.pdf |url=https://www.opcw.org/chemical-weapons-convention/download-convention |access-date=2024-07-26 |website=OPCW |page=124 |language=en}}</ref>

==Chemistry and Synthesis==

===Reactions===

Tabun can be deactivated chemically using common oxidizing agents such as sodium hypochlorite.<ref>{{Cite web |title=Sodium Hypochlorite - Medical Countermeasures Database - CHEMM |url=https://chemm.hhs.gov/countermeasure_sodium-hypochlorite.htm |access-date=2023-11-25 |website=chemm.hhs.gov}}</ref>

===Historic synthesis===

Tabun was made on an industrial scale by Germany during World War II, based on a process developed by [[Gerhard Schrader]]. In the chemical agent factory in [[Brzeg Dolny|Dyhernfurth an der Oder]], code-named "Hochwerk", at least 12,000 metric tons of this agent were manufactured between 1942 and 1945. The manufacturing process consisted of two steps (see below)<!--, the first being reaction of gaseous [[dimethylamine]] ('''1''') with an excess of [[phosphoryl chloride]] ('''2'''), yielding dimethylamidophosphoric dichloride ('''3''', codenamed "Produkt 39" or "D 4") and dimethylammonium chloride ('''4'''). The [[dimethylamidophosphoric dichloride]] thus obtained was purified by vacuum distillation and thereafter transferred to the main tabun production line. Here it was reacted with an excess of [[sodium cyanide]] ('''5'''), dispersed in dry [[chlorobenzene]], yielding the intermediate [[dimethylamidophosphoric dicyanide]] (not depicted in the scheme) and [[sodium chloride]] ('''8'''); then, absolute [[ethanol]] ('''6''') was added, reacting with the dimethylamidophosphoric dicyanide to yield tabun ('''7''') and [[hydrogen cyanide]] ('''9'''). A-->; after the reactions, the mixture (consisting of ~75% solvent, ~25% desired product, plus insoluble salts and reactants)<!--the rest of the hydrogen cyanide--> was filtered <!--to remove the insoluble salts -->and vacuum-distilled.<!--to remove hydrogen cyanide and excess chlorobenzene, so--> This yielded a technical product consisting either of 95% <!--tabun with 5% chlorobenzene (Tabun A) or (later in the war) of--> or 80% tabun <!--with 20% chlorobenzene -->(then known as Tabun A or B, respectively,{{Inconsistent|date = March 2024}} the second a product later in the war).<ref name=Lohs1967>{{cite book |last=Lohs |first=K. |date=1967 |chapter = 3. Gifte, deren Wirkung sich hauptsächlich auf das Nervensystem bzw. [beziehungsweise] auf lebenswichtige Enzyme erstreckt [Poisons, mainly affecting the nervous system, in particular involving vital enzymes]|title= Synthetische Gifte: Zur Chemie, Toxikologie und zu Problemen ihrer völkerrechtswidrigen Anwendung durch imperialistische Armeen |edition= überarb. u. erg. [rev. and expand.] |language=German |trans-title=Synthetic poisons: On the chemistry, toxicology and problems of their illegal use by imperialist armies |url=https://www.gbv.de/dms/weimar/toc/182750841_toc.pdf | access-date=31 March 2024 | location = Berlin [East] | publisher = Militärverlag der Deutschen Demokratischen Republik (Military Publisher's of the [[German Democratic Republic]])}}{{better source|date = March 2024}} The translations of chapter and book title here were editor-generated.</ref>{{verification needed|date = March 2024}}{{better source|date = March 2024}}

[[Image:TabunSynthesis.png|400px]]

==Effects of exposure==

The symptoms of exposure include:<ref name="cbw">{{cite web |title=Nerve Agent: GA |url=http://www.cbwinfo.com/Chemical/Nerve/GA.shtml |url-status=dead |archive-url=https://web.archive.org/web/20110927051929/https://www.cbwinfo.com/Chemical/Nerve/GA.shtml |archive-date=2011-09-27 |access-date=2008-11-06 |publisher=Cbwinfo.com}}</ref><ref name=military>{{cite web |url=http://usmilitary.about.com/library/milinfo/blchemical-3.htm |title=Chemical Warfare Weapons Fact Sheets&nbsp;— Tabun&nbsp;— GA Nerve Agent |publisher=Usmilitary.about.com |access-date=2008-11-06 |url-status=dead |archive-url=https://web.archive.org/web/20160303185700/http://usmilitary.about.com/library/milinfo/blchemical-3.htm |archive-date=2016-03-03 }}</ref><ref name=ency>{{Cite web|url=https://www.encyclopedia.com/science-and-technology/chemistry/organic-chemistry/tabun#3403300733|title=Tabun &#124; Encyclopedia.com|website=www.encyclopedia.com}}</ref> [[Anxiety|nervousness]]/[[anxiety|restlessness]], [[miosis]] (contraction of the pupil), [[rhinorrhea]] (runny nose), excessive salivation, [[dyspnea]] (difficulty in breathing due to [[bronchoconstriction]]/secretions), [[sweating]], [[bradycardia]] (slow heartbeat), [[Syncope (medicine)|loss of consciousness]], [[convulsion]]s, [[flaccid paralysis]], loss of bladder and bowel control, [[apnea]] (breathing stopped) and lung blisters. The symptoms of exposure are similar to those created by all [[nerve agent]]s. Tabun is toxic even in minute doses. The number and severity of symptoms which appear vary according to the amount of the agent absorbed and rate of entry of it into the body. Very small skin dosages sometimes cause local sweating and tremors accompanied with characteristically constricted pupils with few other effects. Tabun is about half as toxic as [[sarin]] by inhalation, but in very low concentrations it is more irritating to the eyes than sarin. Tabun also breaks down slowly, which after repeated exposure can lead to [[Bioaccumulation|build up in the body]].<ref name="nta">[http://www.nationalterroralert.com/tabun Facts About Tabun], National Terror Alert Response System</ref>

The effects of tabun appear slowly when tabun is absorbed through the skin rather than inhaled. A victim may absorb a lethal dose quickly, although death may be delayed for one to two hours.<ref name=military/> A person's clothing can release the toxic chemical for up to 30 minutes after exposure.<ref name="nta"/> Inhaled lethal dosages kill in one to ten minutes, and liquid absorbed through the [[Human eye|eye]]s kills almost as quickly. However, people who experience mild to moderate exposure to tabun can recover completely, if treated almost as soon as exposure occurs.<ref name="nta"/> The [[median lethal dose]] ([[LD50|LD₅₀]]) for tabun is about 400&nbsp;mg-min/m³.<ref>{{cite web|url=http://www.atsdr.cdc.gov/MHMI/mmg166.html |archive-url=https://web.archive.org/web/20030423050312/http://www.atsdr.cdc.gov/MHMI/mmg166.html |url-status=dead |archive-date=April 23, 2003 |title=ATSDR&nbsp;— MMG: Nerve Agents: Tabun (GA); Sarin (GB); Soman (GD); and VX |publisher=Atsdr.cdc.gov |access-date=2008-11-06}}</ref>

The lethal dose for a man is about .01 mg/kg. The median lethal dose for respiration is 400 mg-minute/m3 for humans. Respiratory lethal doses can kill anytime from 1-10 minutes. When the liquid enters the eye, it also can kill just as quickly. When absorbed via the skin, death may occur in 1-2 minutes, or it can take up to 2 hours. <ref>{{Cite web |last=PubChem |title=Tabun |url=https://pubchem.ncbi.nlm.nih.gov/compound/6500 |access-date=2023-03-02 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>

Treatment for suspected tabun poisoning is often three injections of a nerve agent antidote, such as [[atropine]].<ref name="ency"/> [[Pralidoxime chloride]] (2-PAM Cl) also works as an antidote; however, it must be administered within minutes to a few hours following exposure to be effective.<ref>Emergency Response Safety and Health Database. [https://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750004.html TABUN (GA): Nerve Agent]. National Institute for Occupational Safety and Health. Accessed April 30, 2009.</ref>

==History==

{{details|Nerve agent#History}}

Research into ethyl dialkylaminocyanophosphonate began in the late 19th century, In 1898, Adolph Schall, a graduate student at the [[University of Rostock]] under professor [[August Michaelis]], synthesised the diethylamino analog of tabun, as part of his PhD thesis ''Über die Einwirkung von Phosphoroxybromid auf secundäre aliphatische Amine''.<ref>{{cite journal|last1=Petroianu|first1=Georg|title=Pharmacists Adolf Schall and Ernst Ratzlaff and the synthesis of tabun-like compounds: a brief history|journal=Die Pharmazie |volume=69|issue=October 2014|pages=780–784|doi=10.1691/ph.2014.4028|year=2014|pmid=25985570}}</ref> However, Schall incorrectly identified the structure of the substance as an imidoether, and Michaelis corrected him in a 1903 article in ''[[Liebigs Annalen]]'', ''Über die organischen Verbindungen des Phosphors mit dem Stickstoff''. The high toxicity of the substance (as well as the high toxicity of its precursors, [[diethylamidophosphoric dichloride]] and [[dimethylamidophosphoric dichloride]]) wasn't noticed at the time,{{fact|date = March 2023}} most likely due to the low yield of the synthetic reactions used.{{Speculation inline|date = March 2024}}

Tabun became the first nerve agent known after a property of this chemical was discovered by pure accident in late December 1936<ref name="nta"/><ref name=cbw/><ref>[http://usmilitary.about.com/library/milinfo/blchemical-3.htm Chemical Warfare Weapons Fact Sheets] {{Webarchive|url=https://web.archive.org/web/20160303185700/http://usmilitary.about.com/library/milinfo/blchemical-3.htm |date=2016-03-03 }}, about.com</ref><ref>[http://faculty.washington.edu/chudler/weap.html Chemical Weapons: Nerve Agents], University of Washington</ref><ref name=shorthistory>{{cite web |url=http://www.noblis.org/MissionAreas/nsi/BackgroundonChemicalWarfare/HistoryofChemicalWarfare/Pages/HistoryNerveGas.aspx |title=A Short History of the Development of Nerve Gases |publisher=Noblis.org |access-date=2008-11-06 |url-status=dead |archive-url=https://web.archive.org/web/20110415075621/http://www.noblis.org/MissionAreas/nsi/BackgroundonChemicalWarfare/HistoryofChemicalWarfare/Pages/HistoryNerveGas.aspx |archive-date=2011-04-15 }}</ref> by German researcher [[Gerhard Schrader]].<ref name=shorthistory/> Schrader was experimenting with a class of compounds called [[organophosphate]]s, which kill insects by interrupting their nervous systems, to create a more effective [[insecticide]] for [[IG Farben]], a German chemical and pharmaceutical industry conglomerate, at Elberfeld.{{fact|date = March 2024}} The substance he discovered, as well as being a potent insecticide, was enormously toxic to humans; hence, it was named ''tabun'', a tongue-in-cheek codename{{says who|date = March 2024}} to indicate that the substance was 'taboo' (German: ''tabu'') for its intended purpose.<ref>{{cite news |last1=Everts |first1=Sarah |title=The Nazi origins of deadly nerve gases |url=https://cen.acs.org/articles/94/i41/Nazi-origins-deadly-nerve-gases.html |access-date=13 July 2024 |agency=Chemical & Engingeering News |issue=94, 41 |date=17 October 2016}}</ref>

During [[World War II]], as part of the Grün 3 program, a plant for the manufacture of tabun was established at Dyhernfurth (now [[Brzeg Dolny]], [[Poland]]), in 1939.<ref name=shorthistory/> Run by Anorgana GmbH, the plant began production of the substance in 1942.<ref name=shorthistory/> The reason for the delay was the extreme precautions used by the plant.<ref name=shorthistory/> Intermediate products of tabun were corrosive, and had to be contained in quartz or silver-lined vessels. Tabun itself was also highly toxic, and final reactions were conducted behind double glass walls.<ref name=shorthistory/> Large scale manufacturing of the agent resulted in problems with tabun's degradation over time, and only around 12,500 tons of material were manufactured before the plant was seized by the [[Soviet Army]].{{fact|date = March 2024}} The plant initially produced shells and aerial bombs using a 95:5 mix of tabun and [[chlorobenzene]], designated "Variant A".{{Inconsistent|date = March 2024}} In the latter half of the war, the plant switched to "Variant B",{{Inconsistent|date = March 2024}} an 80:20 mix of tabun and chlorobenzene designed for easier dispersion.<ref name=Lohs1967/>{{verification needed|date = March 2024}}{{better source|date = March 2024}} The Soviets dismantled the plant and shipped it to [[Russia]].{{Citation needed|date=September 2009}}

During the [[Nuremberg Trials]], [[Albert Speer]], Minister of Armaments and War Production for the Third Reich, testified that he had planned to kill [[Adolf Hitler]] in early 1945 by introducing tabun into the [[Führerbunker]] ventilation shaft.{{sfn|Speer|1970| pp=430–31}} He said his efforts were frustrated by the impracticality of tabun and his lack of ready access to a replacement nerve agent,{{sfn|Speer|1970| pp=430–31}} and also by the unexpected construction of a tall chimney that put the air intake out of reach.{{verification needed|date = March 2024}}

The US once considered repurposing captured German stocks of tabun (GA) prior to production of [[Sarin]] (GB).<ref>{{cite journal | author = Kirby, Reid | date = 2006 | title = America's Fifteen-Year Struggle for Modern Chemical Weapons | journal = Army Chemical Review | issue = Jan.–Jun | pages = 42–44 | url = http://www.wood.army.mil/chmdsd/images/pdfs/Jan-June%202006/Kirby-Nerve%20Gas.pdf | url-status = dead | archive-url = https://web.archive.org/web/20170211021417/http://www.wood.army.mil/chmdsd/images/pdfs/Jan-June%202006/Kirby-Nerve%20Gas.pdf | archive-date = 2017-02-11 | access-date = 31 March 2024}}</ref> Like the other [[Allies of World War II|Allied]] governments, the Soviets soon abandoned tabun (GA) for [[Sarin]] (GB) and [[Soman]] (GD).{{fact|date = March 2023}} Large quantities of the German-manufactured agent were dumped into the sea to neutralize the substance.{{fact|date = March 2024}}<!--Content of these two sentences not in the Kirby source just cited.-->

Since GA is much easier to produce than the other G-series weapons{{Citation needed|date=November 2023}} and the process is comparatively widely understood, countries that develop a nerve agent capability but lack advanced industrial facilities often start by producing GA.{{fact|date = March 2024}}

During the [[Iran–Iraq War]] of 1980 to 1988, [[Iraqi chemical attacks against Iran|Iraq employed quantities of chemical weapons against Iranian ground forces]]. Although the most commonly used agents were [[mustard gas]] and [[sarin]], tabun and [[cyclosarin]] were also used.<ref name=ency/><ref>{{Cite web | author = ABC News Staff | date = April 7, 2003 | title = Facts About the Nerve Agent Tabun | work = ABCNews.go.com [[ABC News (United States)|ABC News]] | url=https://abcnews.go.com/US/story?id=90722&page=1 | access-date = 31 March 2024}}</ref>{{better source|date = March 2024}}

Tabun was also used in the 1988 [[Halabja chemical attack]].<ref>{{Cite news|url=http://news.bbc.co.uk/onthisday/hi/dates/stories/march/16/newsid_4304000/4304853.stm|title=1988: Thousands die in Halabja gas attack|date=March 16, 1988|via=news.bbc.co.uk}}</ref>

Producing or stockpiling tabun was banned by the 1993 [[Chemical Weapons Convention]]. The worldwide stockpiles declared under the convention were 2 tonnes, and as of December 2015 these stockpiles had been destroyed.<ref>{{cite report | author = Organisation for the Prohibition of Chemical Weapons | date = 30 November 2016 | title = Report of the OPCW on the Implementation of the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on Their Destruction in 2015 | chapter-url = https://www.opcw.org/documents-reports/annual-reports/ | chapter = Annex 3 | page = 42 | access-date = 8 March 2017}}</ref>

==See also==

* [[Cyclosarin]] (GF)

* [[Deseret Chemical Depot]] – where the remaining US stockpile was destroyed

* [[Operation Sandcastle]] – dumping of World War II German tabun bombs by the UK in 1955–1956

* [[Francis E. Dec]] - Schizophrenic and World War II veteran, spoke about the "Tabin Needle" in rants

==References==

{{reflist|30em}}

== Bibliography ==

* {{citation

| last = Speer

| first = Albert

| author-link = Albert Speer

| year = 1970

| title = Inside the Third Reich |translator=Richard Winston |translator2=Clara Winston

| publisher = Macmillan

| location = New York and Toronto

| isbn = 978-0-297-00015-0

| lccn = 70119132

}}. Republished in paperback in 1997 by Simon & Schuster, {{ISBN|978-0-684-82949-4}}

*: (Original German edition: {{citation

| last = Speer

| first = Albert

| year = 1969

| title = Erinnerungen |trans-title=Reminiscences

| publisher = Propyläen/Ullstein Verlag

| location = Berlin and Frankfurt am Main

| oclc = 639475

}})

==Further reading==

* United States Senate, 103d Congress, 2d Session. (May 25, 1994). [http://www.gulfweb.org/bigdoc/report/appga.html Material Safety Data Sheet—Lethal Nerve Agent Tabun (GA)]. Retrieved Nov. 6, 2004.

* United States Central Intelligence Agency (Jul. 15, 1996) [http://www.fas.org/irp/gulf/cia/960715/72569.htm Stability of Iraq's Chemical Weapon Stockpile] {{Webarchive|url=https://web.archive.org/web/20110428103309/http://www.fas.org/irp/gulf/cia/960715/72569.htm |date=2011-04-28 }}

* {{cite book|last=Norris|first=John|title=NBC: Nuclear, Biological and Chemical Warfare on the Modern Battlefield|publisher=Brassey's UK|year=1997|page=20|isbn=1-85753-182-5}}

{{Chemical warfare}}

{{Acetylcholine metabolism and transport modulators}}

{{Authority control}}

{{DEFAULTSORT:Tabun}}

[[Category:Acetylcholinesterase inhibitors]]

[[Category:G-series nerve agents]]

[[Category:Nitriles]]

[[Category:Ethyl esters]]

[[Category:Organophosphates]]

[[Category:German inventions of the Nazi period]]

[[Category:German chemical weapons program]]