58742-04-4Relevant articles and documents
Sympathomimetic effects of exo- and endo-isomers of 2-aminobenzonorbornene in vitro and in vivo
Burn,Crooks,Ratcliffe,Rees
, p. 87 - 91 (1980)
A stereospecific synthesis of endo-2-aminobenzonorbornene 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.
Syntheses and biological evaluation of 2- and 9-aminobenzonorbornenes as conformationally rigid analogs of amphetamines
Wood,Daniels,Bauer,Gearien
, p. 199 - 204 (2007/10/02)
Isomers of the 2- and 9-aminobenzonorbornenes were prepared as rigid analogs of amphetamine and were employed to study the conformational requirements of indirectly acting sympathomimetic agents. Of this series of isomeric amines, the exo-2 and anti-9 isomers closely resemble the fully extended conformation of amphetamine. The other two amines, the endo-2 and syn-9 isomers, conformationally resemble the folded conformation of amphetamine. The isomers that resemble the extended conformation of amphetamine increased the spontaneous motor activity in mice while the isomers resembling the folded form either decreased or had no effect on motor activity. These compounds also were studied for their ability to accelerate the efflux of tritiated norepinephrine from vesicular and nonvesicular storage sites of isolated perfused rabbit atria; either α-methyl-p-tyrosine- or reserpine-pretreated rabbis were used. Amphetamine and the exo-2 and anti-9 isomers of aminobenzonorbornene could accelerate norepinephrine efflux from either compartment with the endo-2 and syn-9 isomers could accelerate the efflux from only the nonvesicular compartment at the concentrations studied. Fenfluramine and methylphenidate also were studied for their ability to accelerate efflux. Fenfluramine and methylphenidate resembled the aminobenzonorbornenes that correspond to the folded conformation of amphetamine in their ability to accelerate the efflux from nonvesicular storage. However, fenfluramine also resembled amphetamine and the aminobenzonorbornenes corresponding to the extended conformation of amphetamine in its ability to accelerate efflux from vesicular storage sites. The response to methylphenidate was similar to that of the aminobenzonorbornenes resembling the folded conformation of amphetamine.
