The Chemistry of Adrenochrome and Related Compounds

s 60, 5747 (1956). (100) FRANKEL, S., AND ALLERS,R.: Biochem. Z. 18,40 (1909).(101) FRIEDENWALD,J. S., MICHEL,H., AND BUSCHKE,W.: Arch. Biochem. and Biophys. (102) FURTH,0. YON: Hoppe-Seyler’s Z. physiol. Chem. 24, 142 (1898).(103) FURTH,0. VON: Hoppe-Seyler’s 8. physiol. Chem. 26, 15 (1898).(104)FURTH,0. VON: Hoppe-Seyler’s Z. physiol. Chem. 29, 105 (1900).(105) GADDUM,J. H., AND SCHILD,H.: J. Physiol. (London) 80, 9P (1934).(106) GERSHENOVICH,Z. S., KRICHEVSKAYA,A. A., AND ALEKSERKO,L. P.: Ukrain. Biok-him. Zhur. 27, 3 (1955) ; Chem. Abstracts 49, 10470 (1955).(107) GILLETTE,J. R., WATLAND,., AND KALNITSKY,G.: Biochim. et Biophys. Acta 16,526 (1954).(108) GOLDFIEN,A., AND KARLER,R.: Science 127,1292 (1958).(109) GREEN,D. E . , AND RICHTER,D.: Biochem. J. 31, 596 (1937).(110) GREEN,S., MAZUR,A., AND SHORR,E . : J. Biol. Chem. 220, 237 (1956).(111) HAMBERG,U., AND EULER,U. S. VON: Acta Chem. Scand. 4, 1185 (1950).(112) HARLEY-MASON,J.: Experientia 4, 307 (1948).(113) HARLEY-MASON,J . :J. Chem. SOC.1960, 1276.(114) HARLEY-MASON,J . :J. Chem. Soc. 1963, 200.(115) HARLEY-MASON,J . :J. Chem. SOC.1963, 1465.(116) HARLEY-MASON,J., AND BU’LOCK,J. : Nature 166, 1036 (1950).(117) HARLEY-MASON,J., AND LAIRD,A. H.: Biochem. J. 69, 59P (1958).(118) HEACOCK,R. A., AND LAIDLAW,B. D.: Nature 182, 526 (1958).(119) HEACOCK,R. A., AND LAIDLAW,B. D.: Chem. & Ind. (London) 1968, 1510.(120) HEACOCK,R. A., AND MAHON,M. E . : Can. J. Chem. 36, 1550 (1958).(121) HEACOCK,R.A., NERENBERG,C., AND PAYZA,. N.: Can. J . Chem. 36,853 (1958).(122) HEACOCK,R. A., NERENBERQ,C., AND SCOTT,B. D.: Unpublished work.(123) HEARD,R. D. H., AND RAPER,H. S.: Biochem. J. 27,36 (1933).(124) HELLER,J. H., SETLOW,R. B., AND MYLON,E. : Am. J. Physiol. 161, 268 (1950).(125) HESSE,0.:Ann. 141, 82 (1867).(126) HOFFER,A.: J. Clin. Exptl. Psychopathol. & Quart. Rev. Psychiat. Neurol. 18, No.1, 38 (1956).(127) HOFFER,A. : “Adrenochrome and Adrenolutin and their R.elationship to Mental Dis-ease,” in Psychotropic Drugs, edited by S. GARATTINIA N D V. GHETTI,p. 10. Else-vier, Amsterdam (1957).32, 382 (1951). (128) HOGEBOOM,G. H., AND ADAMS,M. H.: J. Biol. Chem. 146, 273 (1942).(129) HOLMES,H. L.: “The Strychnos Alkaloids” in The Alkaloids, edited by R. H. F .MANSKEAND H. L. HOLMES,Vol. I, p. 420. Academic Press, Inc., New York (1950).(130) HOLT,S. J., KELLIE,A. E., O’SULLIVAN,D. G., AND SADLER,P. W. J . : J. Chem. SOC.1968, 1217.(131) HOLTZ,P., AND KRONEBERG,.: Biochem. Z.320,335 (1950).(132) HORNBAKER,E. D., AND BURGER,A.: J. Am. Chem. SOC.77,5314 (1955).(133) HUKKI,J., AND SEPPALAINEN,N.: Acta Chem. Scand. 12, 1231 (1958).(134) HUNZINGER,W. A., RITZEL,G., AND STAUB,H.: Helv. Chim. Acta 39, 2096 (1956).(136) INGLE,D. J., SHEPHERD, . A,, AND HAINES,W. J.: J. Am. Pharm. ASSOC.,Sci. Ed. (136) IWAO,J.: Pharm. Bull. (Tokyo) 4,244 (1956).(137) IWAO,J.: Pharm. Bull. (Tokyo) 4,247 (1956).(138) IWAO,J.: Pharm. Bull. (Tokyo) 4, 251 (1956).(139) IWAO,J., AND KAWAZU,M.: J. Pharm. SOC.Japan 76,811 (1956).37, 375 (1948). CHEMISTRY OF ADRENOCHROME AND RELATED COMPOUNDS 235 (140) IWAO,J., AND TOMINO,K.: J. Pharm. Soc. Japan 76,808 (1956).(141)IWAO,J., AND TOMINO,K.: J. Pharm. Soc. Japan 76, 814 (1956).(142) JACKEROTT, K. A.: Dansk Tidsskr. Farm. 16, 217 (1941).(143) JACKSON,H., A N D KENDALL,. P.: Biochem. J. 44, 477 (1949).(144) JAMES, W. 0.: Nature 161, 851 (1948).(145) JAMES, W. O., AND KILBEY,K.: Nature 166, 67 (1950).(146) JAMES, W. O., ROBERTS,E. A. H., BEEVERS,H., AND KOCH,P. C. DE: Biochem. J. (147) JOBST, J., AND HESSE,0.:Ann. 129, 115 (1864).(148) JORGENSEN, K . S.: Acta Pharmacol. Toxicol. 1,225 (1945).(149) KEHRMANN,F., AND CORDONE,M.: Ber. 46, 3009 (1913).(150) K E R T ~ S Z ,D.: Experientia 6, 473 (1950).(151) K E R T ~ S Z ,D.: Bull. soc. chim. biol. 36, 1157 (1953).(152) KISCH,B.: Exptl. Med. Surg. 5 , 166 (1947).(153) KOELLE,G. B., AND FRIEDENWALD,J. S.: Arch. Biochem. and Biophys. 32,370 (1951).(154) LEUCHS,H., A N D ANDERSON,R. : Ber. 44, 2136 (1911).(155) LEUCHS,H., AND LEUCHS,F . : Ber. 43, 1042 (1910).(156) LEUCHS,H., SEEGER,H., A N D JAEGERS,K. : Ber. 71, 2023 (1938).(157) LOEW,0 . :Biochem. Z. 86, 295 (1918).(158) LUND,A,: Acta Pharrnacol. Toxicol. 6, 75 (1949).(159) LUND,A.: Acta Pharrnacol. Toxicol. 6, 121 (1949).(160) LUND,A.: Acta Pharrnacol. Toxicol. 6, 231 (1949).(161) LUND,A.: Acta Pharrnacol. Toxicol. 6, 137 (1950).(162) MACCARTHY,C. L.: Chiniie & industrie 56, 435 (1946).(163) M~CCIOTTA,E.: Gam. chim. ital. 81, 485 (1951).(164) MACCIOTTA,E.: Boll. lab. chim. provinciali (Bologna, Italy) 6, No. 2,49 (1955); Chem. (165) MANGAN,G. F., AND MASON,J. W.: Science 126, 562 (1957).(166) MANGER,W. M., BALDER,E. J., FLOCH,E . V., BOLLMAN,J. L., BERKSON,J., AND (167) MARQUARDT,P . : Z. ges. exptl. Med. 114, 112 (1944); Chem. Abstracts 44, 2657 (1950).(168) MARQUARDT,P . : Enzymologia 12, 166 (1947).(169) MARQUARDT,P.: Pharmazie 4, 7 (1949).(170) MARQUARDT,P., AND CARL,E . : Naturwissenschaften 39, 210 (1952).(171) MARZAT,J., A N D MESNARD,P . : Trav. soc. pharm. Montpellier 14, 292 (1954); Chem. (172) MARZAT,J., ROMAIN,P., AND MESNARD,P.: Bull. soc. pharm. Bordeaux 92, 16 (1954).(173) MASON,H. S.: J. Biol. Chem. 168, 433 (1947).(174) MASON,H. S.: J. Biol. Chem. 172,83 (1948).(175) MASON,H . S.: Advances in Enzymol. 16, 105 (1955).(176) MASON,H. S., AND WRIGHT,C. I.: J. Biol. Chem. 180,235 (1949).(177) MASSART,L., VANDENRIESSCHE,L., AND DUFAIT,R.: Enzymologia 7, 339 (1939).(178) MAZCR,A,, GREEN,S., AND SHORR,E . : J. Biol. Chem. 220, 227 (1956).(179) MAZZA,F. P., A N D STOLFI,G.: Arch. sei. biol. (Italy) 16, 183 (1931).(180) MESNARD,P., AND MARZAT,J.: Bull. 600. chim. France 1964,859.(181) MESNARD,P., ROMAIN,P., AND MARZAT,J . : Bull. soc. pharm. Bordeaux 92,121 (1954).(182) MORET,V.: Giorn. biochim. 3, 210 (1954); Chem. Abstracts 49, 14067 (1955).(183) MOUFANG,N., AND TAFEL,J.: Ann. 304, 24 (1899). (185) NADEAU,G., JOLY,L. P., AND SOBOLEWSKI,G.: Nature 181, 1061 (1958).(186) NATELSON,S., LOGOVOY,J. K., AND PINCUS,J. B.: Arch. Biochem. 23, 157 (1949).(187) NELSON,J. M., AND DAWSON,C. R.: Advances in Enzymol. 4, 99 (1944).(188) OLIVER,G., AND SCHAEFER,E. A.: J. Physiol. (London) 16, 1P (1894).(189) OSINSKAYA,V. 0.:Biokhimiya 18, 56 (1953); Chem. Abstracts 47, 7579 (1953).43, 626 (1948). Abstracts 60, 2368 (1956).s 60, 2368 (1956). JACOBS, M. : Proc. Staff Meetings Mayo Clinic 28, 526 (1953). Abstracts 49, 5775 (1955).s 49, 5775 (1955). (184) NADEAU,G., AND JOLY,L. P . : KatUre 182, 180 (1958). 236R. A. HEACOCK (190) OSINSKAYA,V. 0.:Biokhimiya 22, 537 (1957); Chem. Abstracts 62, 2211 (1958).(191) OZAKI,T.: TBhoku J. Exptl. Med. 61, 83 (1954); Chem. Abstracts 49, 11953 (1955).(192) OZAWA,H., IWAO,J., KOWA,Y . , NAKAGAMI,S., AND DANNO,T.: J. Pharm. Soc. Ja(193) OZAWA,H., IWAO,J., OKUDA,T., YAMAMOTO,S., SATO,S., HARIGAYA,S., AND HAYA(194) PAGET,M.: Bull. sei. pharmacol. 37, 537 (1930); Chem. Abstracts 26, 532 (1931).(195) PAVOLINI,T., GAMBARIN,F., AND GODENIGO,A. S.: Gam. chim. ital. 81, 527 (1951).(196)PAYZA,. N., AND HOFFER,A , : Unpublished work.(197) PAYZA,. N., AND MAHON,M. E.: In preparation.(198)PEKKARINEN,A., AND PITKANEN,M. E.: Scand. J. Clin. I% Lab. Invest. 7, 1 (1955).(199)PERSKY,H.: Methods of Biochem. Anal. 2, 57 (1955).(200)PERSKY,H., AND ROSTON,S.: Science 118, 381 (1953).(201) PETIT,A.: Compt. rend. 62, 569 (1871).(202)PHILPOT,F. J.: J. Physiol. (London) 97, 301 (1940).pan 76, 1367 (1956). SHI, G.: J. Pharm. Soc. Japan 76, 1408 (1956). I RADLEY,J. A., AND GRANT,J.: Fluorescence Analys i s in Ultra-violet Light, 4th edi-tion, p. 327. Chapman and Hall Ltd., London (1954).RAMIREZ,F., AND OSTWALDEN,P. V O N : J. Org. Chem. 20, 1676 (1955).RANDALL,. 0.: J. Biol. Chem. 166, 733 (1946).RANDALL,L. O., AND HITCHINGS,G. H.: J. Pharmacol. Exptl. Therap. 81, 77 (1944).RANGIER,M.: Compt. rend. 220, 246 (1945).RAPER,H. S.: Biochem. J. 20, 735 (1926).RAPER,H. S.: Biochem. J. 21, 89 (1927).RAPER,H. s.,AND SPEAKMAN,H. B.: Biochem. J. 20,69 (1926).REBI~RE,G.: Chimie et industrie Special No.,384 (Sept. 1925); Chem. Abstracts 20, RICHTER,D., AND BLASCHKO,H.: J. Chem. Soc. 1937, 601.ROBINSON,R., AND SUGASAWA,S.: J. Chem. Soc. 1932,789.ROSTON,S.: Anal. Chem. 30, 1363 (1958).ROZUM,Yu. S.: Biokhimiya 17,476 (1952); Chem. Abstracts 47, 403 (1953).RUIZ-GIRJ~N,J.: Nature 166, 831 (1950).RUIZ-GIRJ~N,J. : Farmacognosia (Madrid) 12, No. 23, 71 (1952) ; Chem. Abstracts 47, RUNTI,C. S.: Gam. chim. ital. 80, 21 (1950).SACCARDI,P.: Gam. chim. ital. 60, 11, 118 (1920).SACCARDI,P.: Biochem.Z. 132,439 (1922).SALWAY,A.H.: J. Chem. Soc. 101, 978 (1912).SCHAYER,. W.: J. Am. Chem. Soc. 74,2441 (1952).SCHAYER,.W., SMILEY,R. L., AND KENNEDY,J.: J. Biol. Chem. 202,425 (1953).SHAW,F. H. : Australian J. Exptl. Biol. Med. Sei. 19, 151 (1941).SHEA,S. M.: Nature 166, 729 (1950).SCHROETER,L. C., HIGUCHI,T., AND SCHULER,E. E.: J. Am. Pharm. Assoc., Sei. Ed. SLATER,E. C.: Biochem. J. 44,305 (1949).SNELL,F. D., AND SNELL,C. T . : Colorimetric Methods of Analys i s , 3rd edition, Vol. SNYDER,F. H., LEVA,E., AND OBERST,F. W.: J. Am. Pharm. Assoc., Sei. Ed. 36, 253477 (1926).