Chemical agents

#This invention relates to the synthesis of new toxic chemical compounds which are useful as chemical warfare agents. More particularly, our invention is concerned with novel compounds produced by means of a quaternizing reaction.

#The chemical agents act mostly on the peripheral cholinergic nervous system which includes the motor nerves, the preganglionic fibers, the ganglia, the postganglionic parasympathetic fibers, and neuromuscular functions. The transmission of impulses along a nerve or from nerve fibers to muscle fibers or secretory cells or from one nerve fiber to another across synapses in ganglia is thought to involve chemical changes either directly or as the source of potential differences.

#Quaternary ammonium compounds in general are known to be physiologically active materials. Mainly because of their positively charged "onium" centers they are attracted by anionic sites in animal tissues, particularly those situated at cell surfaces and interfaces. They can induce physiological responses that mimic or antagonize the action of acetylcholine as a result of their interaction with the various physiological receptor sites of acetylcholine, especially those at membranes of muscle cells. They also combine with enzymes such as acetylcholinesterase, other esterases, acetylcholineacetylase, etc., thus inhibiting their participation in the biological processes.

#(2-Dimethylcarbamoxybenzyl)methylethylamine (1.4 g) and 1,8-dibromooctane (0.8 g) were dissolved in 10 ml of acetonitrile and refluxed on a steam bath for 3 days. After the solution was allowed to cool to room temperature, ethyl acetate (30 ml) was added and an oil separated from the solution. The oil solidified upon stirring in acetone. The crude product thus obtained was collected on a filter and purified by dissolving it in acetonitrile, treating the solution with decolorizing carbon, and adding ethyl acetate. The white crystalline product, 1,8-bis[(2-dimethylcarbamoxybenzyl)ethylamino]octane dimethobromide (0.5 g) was collected and dried, m.p. 176.degree.-178.degree. C.

#Anal. Calcd. for C.sub.34 H.sub.56 Br.sub.2 N.sub.4 O.sub.4 : Calcd: C, 54.8; H, 7.5; Br, 21.5. Found: C, 55.0; H, 7.9; Br, 21.2.

#______________________________________ Toxicity IV LD.sub.50 Rabbits Mice ______________________________________ 0.005 mg/kg 0.007 mg/kg ______________________________________