G. L. Clark, E. A. Parker
1937 Science  
SCIE Found Ag = 63.4 per cent. Theoretical for C2H,02 A g = 64.04 per cent. A solution of these crystals gave no color after diazotization on the addition of dimethyl-a-naphthylamine (no free NH,-group on the benzene ring). After hydrolysis with dilute hydrochloric acid, the substance gave (by colorimetric method) 80.0 per cent. and 78.8 per cent. of para-aminobenzenesulfonamide. Theoretical for CH,CONHC,H,S02NH2= 80.3 per cent. The above data prove the conjugated compound obtained from
more » ... tained from rabbit's urine to be para-acetylaminobenzenesulf onamide. This acetyl derivative has been obtained in several other experiments from the urine of rabbits given large doses of the sulfonamide. The following experiment gives a rough idea of the recovery. A rabbit weighing 1.7 kgm received by mouth 1.7 gms of para-aminobenzenesulfonamide. Ninety cc of urine were secreted in the following 24 hours. This urine was heated just to boiling to dissolve a precipitate, and, while hot, 5 cc were taken and diluted for analysis. From this analysis the remaining 85 cc were calculated to contain 235 mgms of free para-aminobenzenesulfonamide and 1,010 mgms of the conjugated form (calculated as the acetyl compound). The 85 cc of urine were allowed to remain in the ice box for 2 days, the deposited crystals filtered off and dried. Six hundred mgms were obtained. On analysis, these crystals were found to contain 2 per cent. of free sulfonamide and 95 per cent. of the conjugated compound (calculated as the acetyl derivative). After three recrystallizations from water, the compound melted at 218', and when mixed with para-acetylaminobenzenesulfoiiamide (the sample which had been identified) melted at 218'. The second 24-hour urine sample contained a considerable amount of the conjugated compound (by colorimetric analysis). Prom the urine of a patient being treated with the sulfonamide para-acetylaminobenzenesulfonamide has been isolated and identified. A 24-hour specimen of urine measured 980 cc. Analysis of a small sample showed it to contain 1.20 gm of free and 1.25 gm of conjugated compound (calculated as acetyl derivative). The urine was treated with 5 gms of charcoal (Norit), shaken and allowed to stand in the ice box for 8 days (a shorter time is sufficient). The charcoal was removed by filtration, and the filtrate analyzed. The filtrate contained 1.03 gm of the free and 0.25 gm of the conjugated compound. The charcoal was treated with 75 cc of 95 per cent. alcohol, heated for a few minutes on a water bath and allowed to stand over night. The charcoal was removed by filtration, the filtrate evaporated to
doi:10.1126/science.85.2199.203 pmid:17844629 fatcat:ex4wded3lva3lce5ootba3lf44