Synthesis of 2-aminomorphine and 2-aminocodeine. reduction of aromatic nitro groups with formamidinesulfinic acid. / Nithiananda Chatterjie, Arlene Minar and Donald D. Clarke New York State Institute for Basic Research in Mental Retardation, Staten Island, NY 10314

Our interest in the stereoselective reduction of the carbonyl groups of various oxymorphone derivatives with formamidinesulfinic acid (FSA) led to a result indicating that dihydrocodeinone underwent ring-oxygen scission under the conditions of reduction with this reagent. This observation4 has prompted interest and speculation as to the scope and mechanism of this reaction by others, as well as ourselve

Potassium 1,3,3a,8a-tetrahydro-3a,8a-dihydroxy-2,8-dioxoindeno[1,2-d]imidazole-2-ethanesulfonate, K+.C12H11N2O7S- / by D. D. Bray and D. D. Clarke Chemistry Department, Fordham University, Bronx, Nyew York 10458, USA and N. Chatterjie and B. Sinha Institute for Basic Research in Development Disabilities, 1050 Forest Hill Road, Staten Island, New York 10314, USA

Mr = 366·40, monoclinic, P2/c, Z = 4, a=6·195 (1), b= 17·701 (4), c= 1.2·864 (3)A, P= 116·25(2)0 , V=l387·8A3, Dm=1·74, Dx= 1·754 Mg m-3, CuKa, l = 1·5418 A, ,u = 5·07 mm-1, T= 298 K, F(OOO) = 752, R = 0·074 for 2091 observed independent intensity data. Crystals were prepared by reacting the K salt of ureidotaurine with ninhydrin in acid solution. The product shows that the unsubstituted N -of the ureidotaurine reacts with the central C of ninhydri

Isolation and stereochemical identification of a metabolite of naltrexone from human urine / Nithiananda Chatterjie, James M. Fujimoto, Charles E. Inturrisi, Sandra Reorig, Richard I.H. Wang, David V. Bowen, Frank H. Field, and Donald D. Clarke Department of Pharmacology, Cornell University Medical College (N.C., C.E.I.), Department of Pharmacology, Medical College of Wisconsin (J.M.F., S.R.), Veterans Administrative Center, Wood, Wisconsin (R.I.H.W.), Mass Spectrometry Service Laboratory, The Rockefeller University (D.V.B., F.H.F.), and Department of Chemistry, Fordham University (D.D.C.)

Pooled urine samples from patients receiving 100-200 mg of naltrexone per day orally were extracted; the basic (alkaloid) compounds derived were isolated by preparative thin-layer chromatography. The major metabolite of naltrexone was found to be an epimer of N-cyclopropylmethyl- 14-hydroxy-7,8-dihydronormorphine wherein the 6-keto group of naltrexone had been reduced to yield the 6β-hydroxy epimer (an isomorphine). This conclusion was based on infrared, mass, and nuclear magnetic resonance spectra studies. Furthermore, the reduction product formed in vitro in a soluble chicken liver enzyme system from naltrexone and an in vivo metabolite of naloxone derived from the chicken were found to have the more commonly expected 6α-hydroxy orientatio