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Blicke FF, Burckhalter JH.
J Am Chem Soc. 1942 Mar;64(3):477-80.
It is a matter of some interest to compare the pharmacological properties of substances which contain a phenyl radical with corresponding alpha-thienyl compounds.
In this paper we have described a series of alpha-thienylaminoalkanes which were examined pharmacologically by L. W. Rowe in the Parke, Davis and Company laboratories. As far as ability to affect blood pressure is concerned, the behavior of a given member of the thienylaminoalkane series is remarkably similar, at least semiquantitatively, to that of the corresponding phenylaminoalkane (Table I).
Although two of our products have been reported in the chemical literature, we obtained them by different procedures. Putokhin and Egorova prepared alpha-thienylaminomethane but apparently did not examine it pharmacologically. The synthesis of 1-( a-thienyl) -2-aminoethane has been described by Barger and Easson and a pharmacological study was published by Tainter. It was said to be quantitatively indistinguishable from 1-phenyl -2-aminoethane from the standpoint of pressor activity. 1-( a-Phenyl-a’-thienyl)-2-aminoethane and 1-(a-p-anisyl-a’-thieny-l2) aminoethane have been shown to be pressor agents.
Summary: The preparation of twelve alpha-thienylaminoalkanes has been described.
From comparisons, in those instances in which pharmacological data are available, it has been found that the thienyl amines behave entirely similarly to analogous amines of the benzene series as far as pressor activity is concerned.