THIO AND THIOMETHYL-AMMONIUM COMPOUNDS

We have recently (8) discussed the pharmacological action of a number of alkyl sulfonium compounds, i.e., compounds analogous to quaternary ammonium hydroxides, betaines and ethers of choline in which the nitrogen was replaced by sulfur. Lt was found that the action of these sulfur compounds was strikingly like that of the analogous nitrogen compounds, the chief difference being that the nitrogen compounds were more active, due, appar-ently to the presence of the additional alkyl group. We have investigated a series of compounds in which sulfur has replaced the oxygen in choline and formocholine ethers. Only the trimethyl-ammonium compounds will be considered at present; for compounds with other alkyl groups have, as has been pointed out in a number of earlier papers, quite different pharmacological properties and, as will be discussed in a later paper, we have found the same to be true of the sulfur analogues of alkyl-ammonium compounds. (It may be noted, however, that a number of hetero-cyclic compounds produce physiological effects very similar to those caused by the methyl compounds (5).) The only compounds of this class which seem to have been studied previously are , i3’-thiobis (ethyltrimethylammonium chloride) and,, $‘-thiobis (ethyldimethyl-hydroxyethyl am-monium chloride) (4)-compounds formed by the addition of tn-methylamine and dimethyl-$-hydroxyethylamine to $, $‘dichloro-ethyl sulphide. The first of these compounds was perhaps eight times as active as choline, and apparently more active than dicho