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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Hemicholinium-3 congeners as potential antagonists to organophosphate-induced toxicity.

A series of congeners of hemicholinium-3, in which the 1,4-oxazinium rings of hemicholinium are replaced by pyrrolidine, piperidine, 1,3-dioxane, or 1,4-oxazine rings, is described. Several of the target compounds produced blockade of neuromuscular transmission in the rabbit, and three heterocyclic derivatives, 10, 11, and 13, significantly antagonized paraoxon-induced lethality in mice. 1,3-Dioxane derivative 11 was an extremely potent antagonist of paraoxon-induced toxicity in mice, compared with prototypical protective agents physostigmine and pyridostigmine. Compound 11 exhibited a much more favorable therapeutic ratio than the reference drugs. The mechanism of action of 11 has not been elucidated, although it is concluded that it differs from that of hemicholinium-3 (inhibition of high-affinity, sodium-dependent uptake of choline into nerve terminals).[1]


  1. Hemicholinium-3 congeners as potential antagonists to organophosphate-induced toxicity. Cannon, J.G., Sahin, M.F., Long, J.P., Flynn, J.R., Bhatnagar, R.K. J. Med. Chem. (1990) [Pubmed]
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