Centrally acting emetics. 10. Rigid dopamine congeners derived from octahydrobenzo[f]quinoline

Publisher Website
Google Scholar
Abstract
In a study of conformational requirements for certain dopaminergic agonist molecules, a series of conformationally predictable dopamine congeners related to cis- and trans-octahydrobenzo[f]quinoline was prepared. The complexity and equivocal character of the reduction of variously substituted 4-methyl-1,2,3,4,5,6-hexahydrobenzo[f]quinolines were demonstrated and studied. Several literature methods for reduction of these systems were in error regarding the stereochemical nature of the product(s). Geometrically specific and predictable reductions of these hexahydrobenzo[f]quinolines seem unlikely to attain, and a plausible rationalization was proposed. Pharmacologic data on the compounds prepared are consistent with earlier proposals of a biologically significant conformation of dopamine for emesis, the pecking syndrome in pigeons, and other physiological effects.
Keywords