Molecular modeling has been employed to design a new group of cannabimimetic 1-alkyl-2-methyl-3-(1-naphthoyl)indoles. Cannabinoid activity was evaluated in vivo in the mouse and in vitro by determining the binding to the cannabinoid receptor. Maximum activity was found for the 1-butyl, pentyl and hexyl analogs. A rationalization for the alignment of these indoles with traditional cannabinoids is presented.