Adamsite

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Adamsite
Structural formula of adamsite
Names
Preferred IUPAC name
Dibenzo-1-chloro-1,4-arsenine
Systematic IUPAC name
10-Chloro-5,10-dihydrophenarsazinine
Other names
10-Chloro-5H-phenarsazinine
Diphenylaminechlorarsine
Identifiers
3D model (JSmol)
Abbreviations DM
ChemSpider
ECHA InfoCard 100.008.577 Edit this at Wikidata
EC Number
  • 209-433-1
MeSH Phenarsazine+chloride
  • InChI=1S/C12H9AsClN/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8,15H checkY
    Key: PBNSPNYJYOYWTA-UHFFFAOYSA-N checkY
  • InChI=1/C12H9AsClN/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8,15H
    Key: PBNSPNYJYOYWTA-UHFFFAOYAA
  • Cl[As]2c1ccccc1Nc3c2cccc3
  • Cl[As]1C2=C(NC3=C1C=CC=C3)C=CC=C2
Properties
C12H9AsClN
Molar mass 277.58 g·mol−1
Appearance Yellow-green crystals
Melting point 195 °C (383 °F; 468 K)
Boiling point 410 °C (770 °F; 683 K)
0.064 g dm-3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Adamsite or DM is an organic compound; technically, an arsenical diphenylaminechlorarsine, that can be used as a riot control agent. DM belongs to the group of chemical warfare agents known as vomiting agents or sneeze gases.[1] First synthesized in Germany by Heinrich Otto Wieland in 1915, it was independently developed by the US chemist Roger Adams (for whom it is named) at the University of Illinois in 1918. DM was produced and stockpiled by the Americans at the end of World War I, but never deployed on the battlefield. It was, however, used against the Bonus Army who demonstrated in Washington, DC, during the spring and summer of 1932, reportedly causing the death and serious injury of several children who had accompanied their parents on the protests.

DM is an odourless crystalline compound with a very low vapour pressure. The colour of the crystals ranges from bright yellow to dark green depending on the purity. It is readily soluble in some organic solvents (e.g., acetone, dichloromethane), but nearly insoluble in water. In vaporous form it appears as a canary yellow smoke.[2]

Adamsite is usually dispersed as an aerosol, making the upper respiratory tract the primary site of action. Although the effects are similar to those caused by typical riot control agents (e.g. CS), they are slower in onset and longer in duration, often lasting several hours.[1] After a latency period of 5–10 minutes irritation of the eyes, lungs and mucous membranes develops followed by headache, nausea and persistent vomiting.[1]

DM is now regarded as obsolete. It has been widely replaced by riot control agents such as CS which are less toxic and more rapid in onset of symptoms. Early battlefield use was intended to be via "Adamsite candles". These were large metal tubes containing a smoke composition made of Adamsite plus a slow burning pyrotechnic composition. A series of candles were lit and the Adamsite-laden smoke allowed to drift towards the enemy.

North Korea has been accused of producing Adamsite at its Aoji-ri Chemical Complex for stockpiling.[3]

References

  1. ^ a b c Committee on Review and Evaluation of the Army Non-Stockpile Chemical Materiel Disposal Program, U.S. National Research Council. Disposal of Chemical Agent Identification Sets, (Google Books), p. 15, National Academies Press, 1999, (ISBN 0-309-06879-7).
  2. ^ Adamsite (DM) Vomiting Agent. National Institute for Occupational Safety and Health. August 22, 2008. Retrieved December 22, 2008.
  3. ^ Chemical Agents: Adamsite. Nuclear Threat Initiative (NTI). March 2003.

External links