OXYTOCIC ACTIVITY OF BASIC (AMINOMETHYL) DERIVATIVES OF PHENOLS AND RELATED COMPOUNDS

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Abstract
A series of piperidinomethyl and related derivatives of naphthols, substituted phenols and indoles has been tested for oxytocic activity, using in vitro and in vivo methods of assay. Some of the compounds possessed very high activity, exceeding that of ergometrine. Activity was not associated with any structural resemblance to the ergot alkaloids. Highest activity occurred with 2-piperidinomethyl derivatives of phenols, among which maximum potency was conferred by substitution, at both the 4- and 5- positions, by methyl or ethyl or by linkage of these positions to form an indane derivative. In all series, piperidinomethyl derivatives were more active than those formed with other bases and methylation in the position α- to the nitrogen atom augmented the activity of both piperidine and morpholine derivatives. Among 2′-methyl piperidinomethyl phenols, the (—) form was more active than the (+). Acylation or alkylation of the phenolic hydroxyl group did not affect activity. The oxytocic activity was specific, the compounds being less effective upon other forms of smooth muscle. Effects upon blood pressure and respiration of a central nature were observed.

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