Synthesis of (+/-)-1-amino-6,7,8,8a-tetrahydro acenaphthene with possible central dopaminergic activity

We describe the non stereoselective synthesis of (+/-)-1-amino-6,7,8,8a-tetrahydroacenaphthene (14), a novel compound that belongs to the acetanaphtene group, that is presented as a rigid non hydroxylated 2-aminoindan which has a structural disposition of a dopaminergic pharmacophore that possess a phenylethylamine fragment. Intracerebroventricular administration of this compound induces an increase in urinary volume and sodium excretion in conscious rats. The renal actions of 14 were blocked by haloperidol pretreatment, suggesting that 14 acts centrally through a dopaminergic mechanism.