Adamsite

From Infogalactic: the planetary knowledge core
(Redirected from Diphenylaminechloroarsine)
Jump to: navigation, search
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
578-94-9 N
Abbreviations DM
ChemSpider 10884 YesY
EC Number 209-433-1
Jmol 3D model Interactive image
Interactive image
MeSH Phenarsazine+chloride
PubChem 11362
  • InChI=1S/C12H9AsClN/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8,15H YesY
    Key: PBNSPNYJYOYWTA-UHFFFAOYSA-N YesY
  • 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).
N verify (what is YesYN ?)
Infobox references

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 British and the United States at the end of World War I. It was used by the British during the incursions ar Murmansk and Archangel.[2] In the US, it was used against the Bonus Army who demonstrated in Washington, DC, in 1932, reportedly causing the death and serious injury of several children who had accompanied their parents on the protests. It was again used in the Vietnam War.[3]

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.[4]

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 cans or tubes (weighing approximately 5 pounds) which contained 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.[5]

In 2003, North Korea was reportedly producing Adamsite at its Aoji-ri Chemical Complex for stockpiling.[6]

References

  1. 1.0 1.1 1.2 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. When Chemical Weapons Were First Dropped From the Air, North Russia 1919 Simon Jones. Imperial War Museum Review. No. 12, 1999. Retrieved September 3, 2015.
  3. Lua error in package.lua at line 80: module 'strict' not found.
  4. Adamsite (DM) Vomiting Agent. National Institute for Occupational Safety and Health. August 22, 2008. Retrieved December 22, 2008.
  5. Lua error in package.lua at line 80: module 'strict' not found.
  6. Chemical Agents: Adamsite. Nuclear Threat Initiative (NTI). March 2003.

External links