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Tabun (nerve agent)

IUPAC name
Properties
(RS)-Ethyl N,N-
Molecular formula: C5H11N2O2P
Dimethylphosphoramidocyanidate
Molar mass: 162.13 g mol−1
Other names
Appearance: Colorless to brown liquid
GA; Ethyl dimethylphosphoramidocyanidate;
Density: 1.0887 g/cm³ at 25 °C
Dimethylaminoethoxy-cyanophosphine oxide;
1.102 g/cm³ at 20 °C
Dimethylamidoethoxyphosphoryl cyanide; Ethyl
Melting point: −50 °C; −58 °F; 223 K
dimethylaminocyanophosphonate; Ethyl ester of
Boiling point: 247.5 °C; 477.5 °F; 520.6 K
dimethylphosphoroamidocyanidic acid; Ethyl
Solubility in water: 9.8 g/100 g at 25 °C
phosphorodimethylamidocyanidate;
7.2 g/100 g at 20 °C
Cyanodimethylaminoethoxyphosphine oxide;
Vapor pressure: 0.07 mmHg (9 Pa)
Dimethylaminoethodycyanophosphine oxide;
EA1205

Tabun or GA is an extremely toxic chemical substance. It is a clear, colorless, and


tasteless liquid with a faint fruity odor.[1] It is classified as a nerve agent because it
fatally interferes with normal functioning of the mammalian nervous system. Its
production is strictly controlled and stockpiling outlawed by the Chemical Weapons
Convention of 1993. Tabun is the first of the so-called G-series nerve agents along with
GB (sarin), GD (soman) and GF (cyclosarin).

Although pure tabun is clear, less-pure tabun may be brown. It is a volatile chemical,
although less so than either sarin or soman.[1]

Tabun can be destroyed with bleaching powder, though the poisonous gas cyanogen
chloride is produced.[2]

Synthesis
Tabun was made on an industrial scale by Germany during World War II, based on a
process developed by Dr. Gerhard Schrader. In the chemical agent factory in
Dyhernfurth an der Oder, codenamed "Hochwerk", at least 12,000 metric tons of this
agent were manufactured between 1942 and 1945. The manufacturing process consisted
of two steps, 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 dimethylamidophos-
phoric 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). After the reaction, the mixture
(consisting of about 75% chlorobenzene and 25% tabun, along with insoluble salts and
the rest of the hydrogen cyanide) was filtered to remove the insoluble salts and vacuum-
distilled to remove hydrogen cyanide and excess chlorobenzene, so yielding the
technical product, consisting either of 95% tabun with 5% chlorobenzene (Tabun A) or
(later in the war) of 80% tabun with 20% chlorobenzene (Tabun B).[3]

Effects of overexposure
The symptoms of exposure include:[2][4][5] nervousness/restlessness, miosis (contraction
of the pupil), rhinorrhea (runny nose), excessive salivation, dyspnea (difficulty in
breathing due to bronchoconstriction/secretions), sweating, bradycardia (slow heart
beat), loss of consciousness, convulsions, flaccid paralysis, loss of bladder and bowel
control, apnea (breathing stopped) and lung blisters. The exact symptoms of over
exposure are similar to those created by all nerve agents. 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. Also, tabun breaks down slowly, which after repeated exposure can lead to
build up in the body.[1]

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.[4] A person's clothing can release the toxic chemical for up to 30
minutes after exposure.[1] Inhaled lethal dosages kill in one to ten minutes, and liquid
absorbed through the eyes kills almost as fast. However, people who experience mild to
moderate exposure to tabun can recover completely, if treated almost as soon as
exposure occurs.[1] The LCt50 for tabun is about 400 mg-min/m3[6]

Treatment for suspected tabun poisoning is often three injections of a nerve agent
antidote, such as atropine.[5] Pralidoxime chloride (2-PAM Cl) also works as an
antidote; however, it must be administered within a period of from minutes to a few
hours following exposure to be effective.[7]

History
For more details on this topic, see Nerve agent: History.

Tabun was the first nerve agent to be discovered by accident in January 1936[1][2][8][9][10]
by the German researcher Gerhard Schrader.[10] Schrader was experimenting with a
class of compounds called organophosphates, 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. Instead of a new
insecticide, he discovered tabun, a chemical enormously toxic to humans as well as
insects.

During World War II, as part of the Grün 3 program, a plant for the manufacture of
tabun was established at Dyhernfurth[10] (now Brzeg Dolny, Poland), in 1939. Run by
Anorgana, GmbH, the plant began production of the substance in 1942.[10] The reason
for the delay was the extreme precautions used by the plant.[10] 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.[10] 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. The plant initially produced shells and
aerial bombs using a 95:5 mix of tabun and chlorobenzene, designated "Variant A", and
in the latter half of the war switched to "Variant B," an 80:20 mix of tabun and
chlorobenzene designed for easier dispersion. The Soviets dismantled the plant and
shipped it to Russia.

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.[11] He said his efforts
were frustrated by the impracticability of tabun and his lack of ready access to a
replacement nerve agent,[11] and also by the unexpected construction of a tall chimney
that put the air intake out of reach.

The US once had a tabun production program,[5] which ended many decades ago. Like
the other Allied governments, the Soviets soon abandoned GA for GB and GD. Large
quantities of the German-manufactured agent were dumped into the sea to neutralize the
substance.

Since GA is much easier to produce than the other G-series weapons and the process is
comparatively widely understood, countries that develop a nerve agent capability but
lack advanced industrial facilities often start by producing GA.

During the Iran–Iraq War, 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.[5][12]
References
1. ^ Jump up to: a b c d e f Facts About Tabun, National Terror Alert Response
System
2. ^ Jump up to: a b c "Nerve Agent: GA". Cbwinfo.com. Retrieved 2008-11-06.
3. Jump up ^ Lohs, KH: Synthetische Gifte. 3., überarb. u. erg. Aufl., 1967,
Deutscher Militärverlag, Berlin (East).
4. ^ Jump up to: a b "Chemical Warfare Weapons Fact Sheets — Tabun — GA
Nerve Agent". Usmilitary.about.com. Retrieved 2008-11-06.
5. ^ Jump up to: a b c d http://www.encyclopedia.com/doc/1G2-3403300733.html
6. Jump up ^ "ATSDR — MMG: Nerve Agents: Tabun (GA); Sarin (GB); Soman
(GD); and VX". Atsdr.cdc.gov. Retrieved 2008-11-06.
7. Jump up ^ Emergency Response Safety and Health Database. TABUN (GA):
Nerve Agent. National Institute for Occupatinal Safety and Health. Accessed
April 30, 2009.
8. Jump up ^ Chemical Warfare Weapons Fact Sheets, about.com
9. Jump up ^ Chemical Weapons: Nerve Agents, University of Washington
10. ^ Jump up to: a b c d e f "A Short History of the Development of Nerve Gases".
Noblis.org. Retrieved 2008-11-06.
11. ^ Jump up to: a b Speer 1970, pp. 430–31.
12. Jump up ^ http://abcnews.go.com/US/story?id=90722&page=1

 Speer, Albert (1970), Inside the Third Reich [Translated by Richard and Clara
Winston], New York and Toronto: Macmillan, 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: Speer, Albert (1969), Erinnerungen [Reminiscences],


Berlin and Frankfurt am Main: Propyläen/Ullstein Verlag, OCLC 639475)