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T-1123

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.

T-1123
Names
Preferred IUPAC name
N,N-Diethyl-N-methyl-3-[(methylcarbamoyl)oxy]anilinium iodide
Other names
AR-16, TL-1217
Identifiers
  • 60398-22-3
3D model (JSmol)
  • Interactive image
ChemSpider
  • 39424
  • 43257
  • DTXSID00975800
  • 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).

Synthesis edit

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 edit

References edit

  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 edit

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

1123, carbamate, based, acetylcholinesterase, inhibitor, investigated, chemical, warfare, agent, starting, 1940, does, through, blood, brain, barrier, charge, quaternary, nitrogen, antidote, atropine, quaternary, ammonium, phenyl, carbamate, ester, bonded, met. 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 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 1HKey XYPQGNNSAIEXIS UHFFFAOYSA N SMILES CC N C CC C1 CC CC C1 OC O NC I Properties Chemical formula C 13H 21I N 2O 2 Molar mass 364 227 g mol 1 Related compounds Related compounds NeostigmineMiotine Hazards Lethal dose or concentration LD LC LD50 median dose 129 mg kg Subcutaneous mice 1 75 mg kg Subcutaneous cats 1 75 mg kg Subcutaneous dogs 1 150 mg kg Subcutaneous rabbits 1 122 5 mg 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 Contents 1 Synthesis 2 See also 3 References 4 Extra readingSynthesis editT 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 editMiotine Neostigmine TL 1238 T 1152 T 1194 TMTFAReferences edit 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 Extra reading editRobinson J P 1971 The Problem of Chemical and Biological Warfare The rise of CB weapons Almqvist amp Wiksell ISBN 9780391002005 nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title T 1123 amp oldid 1206018907, wikipedia, wiki, book, books, library,

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