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During studies of urinary amino acids on clinical material by O. R. J. a hitherto undescribed ninhydrin-positive compound was sometimes observed. The compound, which also gave a positive reaction with iodine-sodium azide reagent, indicating the presence of bivalent sulphur, was found to be of exogenic origin. It was demonstrable only in the urine of subjects dosed with fairly large quantities of acetophenetidine (phenacetin). According to Brodie & Axelrod (1949) about 75 % of an oral dose of acetophenetidine is excreted as conjugated p-acetamidophenol, about 4 % as free p-acetamidophenol, less than 0-2 % as unchanged acetophenetidine, and trace amounts as p-phenetidine. As none of these metabolites gives positive ninhydrin and iodine-azide reactions the compound observed must be a previously unknown metabolite of acetophenetidine. The present paper describes the isolation and partial characterization of this metabolite. EXPERIMENTAL Materials. p-Acetamidophenol and p-phenetidine were kindly supplied by Hoffmann-La Rocbe and Co. A.-G., Basel, Switzerland. 8-p-Aminophenylcysteine was prepared as described by Boyland, Manson & Nery (1962). Other compounds, including acetophenetidine, were of commercial origin. Paper chromatography. Whatman no. 1 chromatography paper was employed for descending development in the solvent system (a) butan-1-ol-acetic acid-water (4: 1: 1, by vol.) and for ascending development in the system (b) phenol-water-aq. NH3 (sp.gr. 0 88) (800:200: 1, by vol.). All runs were performed at 250. When two-dimensional chromatograms were run the technique described by Jagenburg (1959) was used. For the detection of compounds on paper the following reagents were used: (1) ninhydrin (0-2 %, w/v) in butan-1-ol saturated with aq. 4Nacetic acid; (2) aq. NaN3 (0-5 M)-12 (0-01 M) plus KI (0-5M) (1:1, v/v) (Sjoquist, 1953); (3) 01M-K2Cr207-acetic acid (1:1, v/v) followed by AgNO3 (0-1 M) (Knight & Young 1958); (4) Na2CO, (10 %, w/v) followed by diazotized sulphanilic acid [sulphanilic acid (1 %, w/v, in N-HCI) mixed with an equal volume of NaNO2 (5 %, w/v) and allowed to stand for 5 min.

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