Adamsite

Adamsite
Preferred IUPAC name Dibenzo-1-chloro-1,4-arsenine
Systematic name 10-Chloro-5,10-dihydrophenarsazinine
Other names 10-Chloro-5H-phenarsazinine Diphenylaminechlorarsine
Identifiers
Abbreviations	DM
CAS number	578-94-9 Y
PubChem	11362
ChemSpider	10884 Y
EC number	209-433-1
MeSH	Phenarsazine+chloride
Jmol-3D images	Image 1 Image 2
SMILES Cl[As]2c1ccccc1Nc3c2cccc3 Cl[As]1C2=C(NC3=C1C=CC=C3)C=CC=C2
InChI InChI=1S/C12H9AsClN/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8,15H Y Key: PBNSPNYJYOYWTA-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C12H9AsClN
Molar mass	277.58 g mol−1
Exact mass	276.963948417 g mol-1
Appearance	Yellow-green crystals
Melting point	195 °C, 468 K, 383 °F
Boiling point	410 °C, 683 K, 770 °F
Solubility in water	0.064 g dm-3
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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

• Adamsite in the NIOSH emergency response database
• Case definition of adamsite poisoning (from the U.S. CDC)