Sympathomimetic effects of exo- and endo- isomers of 2-aminobenzonorbornene in vitro and in vivo

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Abstract
A stereospecific synthesis of endo-2-aminobenzornorbornene is described. Its sympathomimetic activities and those of its N-methyl derivative were compared with the equivalent exo- isomers using the isolated rat anococcygeus muscle and the anaesthetized rat blood pressure preparations. On the anococcygeus muscle preparation the endo- and exo-isomers of the primary amines had similar indirectly acting sympathomimetic activities. In contrast the exo-N-methyl derivative was a far more potent sympathometic in vitro than the endo-N methyl isomer. In the anaesthetized rat the exo- and endo-isomers of 2-aminobenzonorbornene and their N-methyl derivatives all had similar pressor activities, though the successive injections of the two exo-derivatives suggested an additional α-adrenoceptor blocking activity. The actions of these rigid sympathomimetics are compared with those of the flexible amphetamine structure.