(-)-(3AS)-ESEROLINE CARBAMATE, A CLOSE ANALOG OF PHYSOSTIGMINE

(-)-Eseroline 1 on reaction with trimethylsilyl isocyanate in refluxin g toluene directly gave the crystalline carbamate 5, which is the simp lest carbamate of eseroline whose activity has not previously been rep orted. Surprisingly, unlike physostigmine and numerous analogs, carbam ate 5 was found to possess only low enzyme inhibitory activity against human acetyl-(AChE) and butyrylcholinesterase (BChE) in vitro and onl y minimal action when administered to rats in in vivo studies. Its syn thesis and pharmacology, in comparison to physostigmine and known n-al kyl and aryl carbamates, are reported for the first time.