Abstract
The mechanism by which phenaglycodol causes increased values for urinary 17-ketogenic steroids and 17-ketosteroids has been investigated. On treatment with sodium bismuthate, phenaglycodol yields p-chloroacetophenone; this substance produces a typical blue color in the Zimmermann reaction for 17-ketosteroids. Thus, the presence of phenaglycodol in urine increases the value found for 17-ketogenic steroids. During the acid-catalyzed hydrolysis of conjugated 17-ketosteroids, phenaglycodol undergoes a pinacol rearrangement to form a ketone which gives color when treated with the Zimmermann reagent. The mixture from the Zimmermann reaction, when chromatographed on paper, shows the presence of a pigment which is derived from the ketone. The reaction product of a urinary extract with the Zimmermann reagent contains this pigment if the person whose urine is being tested is ingesting phenaglycodol. Addition of the normal daily dose of phenaglycodol (1,200 mg.) to a 24-hour sample of urine increased the 17-ketogenic steroid value from 4 to 154 mg. and the 17-ketosteroid value from 18 to 30 mg.
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