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T-1123

Names
Preferred IUPAC name N,N-Diethyl-N-methyl-3-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;1HKey: XYPQGNNSAIEXIS-UHFFFAOYSA-N
SMILES CC(C)(CC)C1=CC(=CC=C1)OC(=O)NC.
Properties
Chemical formula	C13H21IN2O2
Molar mass	364.227 g·mol
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 , 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. 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.

See also

• Miotine
• Neostigmine
• TL-1238
• T-1152
• T-1194
• TMTFA

References

1. ^ 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

• Robinson, J. P. (1971). The Problem of Chemical and Biological Warfare: The rise of CB weapons. Almqvist & Wiksell. ISBN 9780391002005.

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