Sympathomimetic effects of exo- and endo-isomers of 2-aminobenzonorbornene in vitro and in vivo.
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 alpha-adrenoceptor blocking activity. The actions of these rigid sympathomimetics are compared with those of the flexible amphetamine structure.
D000661:Amphetamine / Q000494:pharmacology; D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D006339:Heart Rate / Q000187:drug effects; D066298:In Vitro Techniques; D008297:Male; D009119:Muscle Contraction / Q000187:drug effects; D009636:Norbornanes / Q000494:pharmacology*; D009638:Norepinephrine / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism; D013566:Sympathomimetics
D009636:Norbornanes; D013566:Sympathomimetics; C013805:2-aminobenzonorbornene; D000661:Amphetamine; D009638:Norepinephrine