T-1123

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).

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. ^ a b c d e Chemical Warfare Agents, and Related Chemical Problems. Parts I-II. 1958.
  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

Stub icon

This article about an organic compound is a stub. You can help Wikipedia by expanding it.