T-1123 is a
carbamate
In organic chemistry, a carbamate is a category of organic compounds with the general formula and structure , which are formally derived from carbamic acid (). The term includes organic compounds (e.g., the ester ethyl carbamate), formally o ...
-based
acetylcholinesterase inhibitor
Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level and ...
. 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
Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given i ...
.
T-1123 is a quaternary ammonium ion. A
phenyl carbamate
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydroge ...
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
Methyl isocyanate (MIC) is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane and methyl carbylamine. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides (such as carbaryl, c ...
and
methyl iodide
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one h ...
. 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
Miotine is an anticholinesterase drug. Miotine was the first synthetic carbamate that was used clinically.
Unlike the miotine analog neostigmine, it doesn't have a quaternary ammonium group to give it a permanent positive charge. It can exist as ...
*
Neostigmine
Neostigmine, sold under the brand name Bloxiverz, among others, is a medication used to treat myasthenia gravis, Ogilvie syndrome, and urinary retention without the presence of a blockage. It is also used in anaesthesia to end the effects of n ...
*
TL-1238
TL-1238 (Substance 3393) is an extremely potent carbamate acetylcholinesterase inhibitor. It has been shown to be more potent than neostigmine.
See also
* Miotine
*Neostigmine
*T-1123
T-1123 is a carbamate-based acetylcholinesterase inhibitor ...
*
TMTFA
TMTFA is an extremely potent acetylcholinesterase inhibitor. As a transition state analog of acetylcholinesterase, TMTFA is able to inhibit acetylcholinesterase at extremely low concentrations (within the femtomolar range), making it one of the ...
References
Extra reading
*
Carbamate nerve agents
Quaternary ammonium compounds
Phenol esters
Acetylcholinesterase inhibitors
Chemical weapons
Aromatic carbamates
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