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.

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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[PB158508-1] 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.

[1]

[2]

[3]

v t Neurotoxins
Animal toxins	Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx) Epibatidine Zetekitoxin AB Dendrotoxin
Bacterial	Botulinum toxin Tetanospasmin
Cyanotoxins	Anatoxin-a Guanitoxin BMAA Saxitoxin
Plant toxins	Aconitine Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin Thujone Volkensin Veratridine
Mycotoxins	Ibotenic acid Muscarine Muscimol
Pesticides	Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil Phenylsilatrane Chlorophenylsilatrane Sulfuryl fluoride Mipafox Schradan Dimefox
Nerve agents	Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VP VR VX GV EA-3990 EA-4056 T-1123 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) Fluorotabun Chinese VX EA-2192
Bicyclic phosphates	TBPS TBPO IPTBO
Cholinergic neurotoxins	Acetylcholine mustard Catecholine Choline mustard Ethylcholine mustard Hemicholinium mustard
Other	Dimethylcadmium Dimethylmercury Toxopyrimidine IDPN Tetraethyllead

T-1123

Synthesis

See also

References

Extra reading

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