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INCREASES in the amount of androgenic material, assayed biologically, which could be extracted from human urine following administration of androgens, have been reported by Buihler [1933], by McCullagh et al. [1938], who treated a eunuch with urine extract, and by Kochakian [1937]. These were small and uncertain, and were produced by low doses. Dorfman & Hamilton [1939], nsing efficient methods of extraction, have recently reported three cases in which large increases in the amount of androgenic material occurred as a result of the administration of testosterone propionate. Prof. J. W. Cook has carried out chemical work on these extracts [Cook et al. 1939]. Callow et al. [1939, 1, 2] have investigated independently a series of cases in which large doses of hormones were administered. One of these patients, a man under the care of Dr E. P. Sharpey-Schafer, was receiving 100 mg. of testosterone propionate daily. A clinical account of this case has been published elsewhere [Schrire & SharpeySchafer, 1939, case 3]. During the administration of testosterone propionate the excretion of 17-ketosteroids (measured colorimetrically by the modified Zimmermann reaction described by Callow et al. [1938]), and of androgenic activity, increased to about four times the level of that of a subsequent control period, when this excretion was within normal limits, so that there can be little doubt that the increase was directly caused by the injections; sufficient extract was available for chemical separation of the 17-ketosteroids, with which the urine was enriched, to be attempted. The neutral fraction of the benzene extract of acid-hydrolysed urine was separated into ketonic and non-ketonic fractions by the Girard-Sandulesco reagent P. The ketonic fraction after chromatographic adsorption followed by elution of the column yielded androsterone and a compound which was identified as aetiocholan-3(a)-ol-17-one (Fieser's nomenclature [1937]; the "epi-oxyaetiocholanon-17 " of Ruzicka & Goldberg [1935]). A total of 60 mg. of crude androsterone and 58 mg. of crude aetiocholan-3(ao)-ol-17-one were obtained from 71 1. of urine or about 61 days' output. As a control, the extract from 50 1. of a bulk collection of normal men's urine was put through the same process. A total of 60 mg. of androsterone and 70 mg. of crude aetiocholan-3(oc)-ol-17-one were separated. The isolation of the latter compound from normal urine has not previously been reported. Thus from the patient receiving testosterone propionate 8 mg./l. of crude androsterone and 7 7 mg./I. of crude aetiocholan-3(oc)-ol-17-one were isolated, while from the normal men's urine the same two compounds were obtained in yields of 1-2 and 1-4 mg./l. respectively. The androsterone which was isolated accounts for about 74% of the androgenic activity, assayed on capons, of the extracts of the "testosterone urine", and about 45 % of the activity of the normal urine extract.

The isolation of two transformation products of testosterone from urine