No abstract

No abstract

The little compound 1a has been prepared and was found to be a strong, orally active agonist with narcotic--antagonist properties. 1a was prepared by two independent routes: (1) nitration of volazocine and subsequent reduction and (b) a sequence involving dissolving metal reduction of cyclazocine methyl ether, followed by oximination and Semmler--Wolff rearrangement. Several analogues were prepared and tested.

May's benzomorphan synthesis leads not only to the alpha or cis isomer and the beta or trans isomer but also to a position isomer hereinafter called the gamma isomer. The structure and synthesis of this isomer are described. Biological activities of the alpha and gamma isomers are compared.

When 0.9 g. of this substance was boiled and stirred for five hours with 125 ml. of acetic acid containing 14 g. of chromic anhydride and 5 ml. of epned. sulfuric acid, it gave 0.96 g. (96%) of crude dibasic acid, m. p. 400°with decomposition. The substance was insoluble in aqueous or alcoholic alkali and in all organic solvents except hot quinoline. Recrystallized from quinoline and then digested with boiling alcohol for thirty minutes, the pt.pupr quinquebenzone-£i,/>«-dicarboxylic add formed a colorless powder that sintered at 400°and melted at 405-410°with decomposition.