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Reactivators of Inhibited Acetylcholinesterase. I. the Preparation and Properties of 4‐Hydroxyminomethyl‐1‐Methylpyrimidinium Iodide
Author(s) -
Ashani Y.,
Edery H.,
Zahavy J.,
Künberg W.,
Cohen Sasson
Publication year - 1965
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196500038
Subject(s) - chemistry , acetylcholinesterase , iodide , oxime , organophosphate , nitrosation , alkylation , atropine , pyrimidine , cholinesterase , acetylcholine , methyl iodide , in vitro , medicinal chemistry , organic chemistry , stereochemistry , enzyme , pharmacology , biochemistry , catalysis , medicine , anesthesia , pesticide , agronomy , biology
4‐Hydroximinomethyl‐pyrimidine (VIII) has been prepared from 4‐methylpyrimidine (III) by nitrosation or, more preferably, by the Ortoleva‐King procedure. The oxime VIII has a syn configuration and yields, upon alkylation with iodomethane, 4‐hydroximinomethyl‐1‐methyl‐pyrimidinium iodide (IX). The latter proved to be a reactivator of phosphorylated acetylcholine esterase in vitro. In combination with low doses of atropine it also protected mice against organophosphate intoxication.