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
CAS Number	60398-22-3;
3D model (JSmol)	Interactive image;
ChemSpider	39424;
PubChem CID	43257;
CompTox Dashboard (EPA)	DTXSID00975800 ;
	InChI 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;
	SMILES CC[N+](C)(CC)C1=CC(=CC=C1)OC(=O)NC.[I-];
Properties
Chemical formula	C13H21IN2O2
Molar mass	364.227 g·mol−1
Related compounds
Related compounds	Neostigmine; Miotine
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	129 μg/kg (Subcutaneous, mice); 75 μg/kg (Subcutaneous, cats); 75 μg/kg (Subcutaneous, dogs); 150 μg/kg (Subcutaneous, rabbits); 122.5 μg/kg (Intramuscular, rats)
	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]

References

^ ^a ^b ^c ^d ^e Chemical Warfare Agents, and Related Chemical Problems. Parts I-II. 1958.
^ 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.
^ Gupta, Ramesh C. (2015). Handbook of Toxicology of Chemical Warfare Agents. Academic Press. pp. 338–339. ISBN 9780128004944.