The synthesis of a series of β-naphthylamine derivatives closely corresponding to a portion of the apomorphine molecule was undertaken to investigate structure-activity relationships of this centrally active emetic. Employing independent synthetic routes, derivatives of 2-amino-5,6-naphthalenediol and of 2-amino-1,2,3,4-tetrahydronaphthalene-5,6-diol have been prepared. Biological test data are presented. © 1969, American Chemical Society. All rights reserved.