T-1123
Names
Preferred IUPAC name
N,N-Diethyl-N-methyl-3-[(methylcarbamoyl)oxy]anilinium iodide
Other names
AR-16, TL-1217
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C13H20N2O2.HI/c1-5-15(4,6-2)11-8-7-9-12(10-11)17-13(16)14-3;/h7-10H,5-6H2,1-4H3;1H
    Key: XYPQGNNSAIEXIS-UHFFFAOYSA-N
  • CC[N+](C)(CC)C1=CC(=CC=C1)OC(=O)NC.[I-]
Properties
C13H21IN2O2
Molar mass 364.227 g·mol−1
Related compounds
Related compounds
 Neostigmine
Miotine
Hazards
Lethal dose or concentration (LD, LC):
129 μg/kg (Subcutaneous, mice)[1]
75 μg/kg (Subcutaneous, cats)[1]
75 μg/kg (Subcutaneous, dogs)[1]
150 μg/kg (Subcutaneous, rabbits)[1]
122.5 μg/kg (Intramuscular, rats)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

T-1123 is a carbamate-based acetylcholinesterase inhibitor. It was investigated as a chemical warfare agent starting in 1940. It does not go through the blood-brain barrier due to the charge on quaternary nitrogen. The antidote is atropine.[3] T-1123 is a quaternary ammonium ion. A phenyl carbamate ester is bonded in the meta position to the nitrogen on a diethylmethyl amine. The chloride and methylsulfate salt of T-1123 is TL-1299 and TL-1317, respectively.

Synthesis

T-1123 can be produced from m-diethylaminophenol, methyl isocyanate and methyl iodide. First, m-diethylaminophenol is reacted with methyl isocyanate to produce a methylcarbamate. The resulting methylcarbamate is then reacted with methyl iodide to produce T-1123.[1]

See also

References

  1. 1 2 3 4 5 Chemical Warfare Agents, and Related Chemical Problems. Parts I-II.
  2. ↑ Bajgar, J; Patocka, J (1976). "Anticholinesterase action of 3-diethylaminophenyl-N-methyl-carbamate methiodide in vitro and in vivo". Acta Biologica et Medica Germanica. 35 (3–4): 479–84. PMID 970052.
  3. ↑ Gupta, Ramesh C. (2015). Handbook of Toxicology of Chemical Warfare Agents. Academic Press. pp. 338–339. ISBN 9780128004944.

Extra reading

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.