T-1123

{{Chembox

| Name = T-1123

| ImageFile = T-1123.svg

| PIN = N,N-Diethyl-N-methyl-3-[(methylcarbamoyl)oxy]anilinium iodide

| OtherNames = AR-16, TL-1217

| Section1 = {{Chembox Identifiers

| ChemSpiderID = 39424

| PubChem = 43257

| CASNo = 60398-22-3

| StdInChI= 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

| StdInChIKey= XYPQGNNSAIEXIS-UHFFFAOYSA-N

| SMILES = CC[N+](C)(CC)C1=CC(=CC=C1)OC(=O)NC.[I-]

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| Section2 = {{Chembox Properties

| C = 13 | H =21 | N = 2 | O = 2 |I=1

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| Section3 = {{Chembox Related

| OtherCompounds = Neostigmine
Miotine

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| Section4 = {{Chembox Hazards

| LD50 = 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){{cite journal |last1=Bajgar |first1=J |last2=Patocka |first2=J |title=Anticholinesterase action of 3-diethylaminophenyl-N-methyl-carbamate methiodide in vitro and in vivo. |journal=Acta Biologica et Medica Germanica |date=1976 |volume=35 |issue=3–4 |pages=479–84 |pmid=970052}}

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| Section5 =

| Section6 =

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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.{{cite book|last1=Gupta|first1=Ramesh C.|title=Handbook of Toxicology of Chemical Warfare Agents|date=2015|publisher=Academic Press|isbn=9780128004944|pages=338–339|url=https://books.google.com/books?id=MXKDBAAAQBAJ&pg=PA338|language=en}} 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.{{cite book |title=Chemical Warfare Agents, and Related Chemical Problems. Parts I-II |date=1958 |url=https://ntrl.ntis.gov/NTRL/dashboard/searchResults/titleDetail/PB158508.xhtml}}

See also

References

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Extra reading

  • {{cite book|last1=Robinson|first1=J. P.|title=The Problem of Chemical and Biological Warfare: The rise of CB weapons|date=1971|publisher=Almqvist & Wiksell|isbn=9780391002005|url=https://books.google.com/books?id=ZwqIAAAAIAAJ|language=en}}

{{Chemical agents}}

{{Neurotoxins}}

{{Acetylcholine metabolism and transport modulators}}

Category:Carbamate nerve agents

Category:Quaternary ammonium compounds

Category:Phenol esters

Category:Acetylcholinesterase inhibitors

Category:Chemical weapons

Category:Aromatic carbamates

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