RT Journal Article SR Electronic T1 STUDIES OF PHENANTHRENE DERIVATIVES III. DI-SUBSTITUTION PRODUCTS JF Journal of Pharmacology and Experimental Therapeutics JO J Pharmacol Exp Ther FD American Society for Pharmacology and Experimental Therapeutics SP 275 OP 289 VO 52 IS 3 A1 NATHAN B. EDDY YR 1934 UL http://jpet.aspetjournals.org/content/52/3/275.abstract AB Twenty di-substitution phenanthrene compounds are described in comparison with mono-substitution derivatives containing the same groups attached to the phenanthrene nucleus. In general the di-substitution products are less active than the related single substitution phenanthrenes. Exceptions are noted in which the two groups are attached in the 9- and 10-, or in the 3- and 4- positions. Not all of the phenanthrenes containing groups in these positions, however, show increased activity. The most active compounds encountered in this series are 3-4-dihydroxyphenanthrene, and 3-hydroxy-4-aminophenanthrene. Both exhibit considerable toxicity and well-marked analgesic, depressant and emetic effects. Muzzling both hydroxyls of 3-4-dihydroxyphenanthrene by acetyl groups decreases effectiveness just as did muzzling the single hydroxyl of 2- or 3-hydroxyphenanthrene. The introduction of a 4-5-oxygen bridge in the formation of the morphenols does not increase the activity of hydroxy- and alkoxyphenanthrenes.