The Aminochromes.

Anderson, A.B.: Inactivation of Serum Alkaline Phosphatase by Adrenaline and Related Substances. Biochemic. J. 45, xxxvi (1949).Google Scholar

Austin, J., J. D. Chanley and H. Sobotka: The Rearrangement of Epinochrome. J. Amer. Chem. Soc. 73, 2395 (1951).CrossRefGoogle Scholar

H. Sobotka — Hydrogenation of Epinochrome. J. Amer. Chem. Soc. 73, 5299 (1951).CrossRefGoogle Scholar

Bacq, Z. M.: La semicarbazone de l’adrénochrome. C. R. Séances Soc. Biol. 141, 536 (1947)Google Scholar

Bacq, Z. M. et P. Fischer: Sur l’existence de l’adrénaline-quinone. Arch. int. Physiol. 57, 271 (1949–50).CrossRefGoogle Scholar

Ball, E. G. and T. T. Chen: Studies on Oxidation-Reduction. XX. Epinephrine and Related Compounds. J. Biol. Chem. 102, 691 (1933).Google Scholar

Barer, R., H. Blaschko and H. Langemann: Iodochromes of Substances Related to Adrenaline. J. Physiol. 112, 21P (1951).Google Scholar

Barsel, N.: Therapeutic Complexes. U. S. Patent 2691662, 12 October (1954).Google Scholar

— Adrenochrome Isonicotinic Acid Hydrazone. U. S. Patent 2728772, 27 December 1955.Google Scholar

Beaudet, C.: Activité optique des produits de réduction de l’adrénochrome. Experientia 6, 186 (1950).CrossRefGoogle Scholar

— Substances nouvelles apparentées à l’adrénochrome. Experientia 7, 291 (1951).Google Scholar

Beaudet, C., F. Debot, H. Lambot et J. Toussaint: La monosemicarbazone de l’adrénochrome. Experientia 7, 293 (1951).CrossRefGoogle Scholar

Bergel, F. and A. L. Morrison: The Oxidation of Adrenaline. J. Chem. Soc. (London) 1943, 48.Google Scholar

Bouvet, P.: Études sur l’adrénochrome. I. Virage de l’adrénochrome et de son dérivé iodé en milieu acide. V. Oxydation de l’adrénaline par l’iode, le brome et l’acide iodique. Ann. pharm. franç. 7, 514, 721 (1949).Google Scholar

Braconier, F., H. Le Bihan et C. Beaudet: L’adrénochrome et ses dérivés. Arch. int. Pharmacodyn. 69, 181 (1943).Google Scholar

Buchnea, D.: Adrenochrome (Reported by C. L. McCarthy). Report No. 47, Off. Pub. Board, Dept. Coram., Washington, D. C. (1945).Google Scholar

Bu’Lock, J. D. and J. Harley-Mason: The Chemistry of Adrenochrome. II. Some Analogues and Derivatives. J. Chem. Soc. (London) 1951, 712.Google Scholar

— Melanin and its Precursors. III. New Syntheses of 5: 6-Dihydroxyindole and its Derivatives. J. Chem. Soc. (London) 1951, 2248.Google Scholar

Bu’Lock, J. D., J. Harley-Mason and H. S. Mason: Hallachrome and Dopachrome. Biochemic. J. 47, xxxii (1950).Google Scholar

Burton, H.: The Oxidation of β-3: 4-Dihydroxyphenylethylmethylamine with Silver Oxide. The Isolation of 5: 6-Dihydroxy-i-methylindole and a Synthesis of 5: 6-Dimethoxy-i-methylindole. J. Chem. Soc. (London) 1932, 546.Google Scholar

Chaix, P., J. Chauvet et J. Jézéquel: Étude cinétique de l’oxydation de l’adrénaline en solution tampon-phosphate. Biochim. Biophys. Acta 4, 471 (1950).CrossRefGoogle Scholar

Chaix, P. et D. Gautheron: Sur l’oxydation de l’acide maléique et l’acide fumarique en presence d’adrénochrome. Biochim. Biophys. Acta 12, 405 (1953).CrossRefGoogle Scholar

Chaix, P., G. A. Morin et J. Jézéquel: Participation des phosphates aux réactions d’oxydation de l’adrénaline. C. R. hebd. Séances Acad. Sci. 230, 790 (1950).Google Scholar

Chaix, P. et C. Pallaget: Caractères comparés de l’oxydation de la noradrénaline et de l’adrénaline évoluant en solution tampon phosphate ou bicarbonate. Biochim. Biophys. Acta 10, 462 (1953).CrossRefGoogle Scholar

Chanley, J. D., N. Barsel and H. Sobotka: Unpublished observations.Google Scholar

Cohen, G. N.: Études sur la mélanisation. I. Sur le premier produit de transformation de l’adrénochrome au cours de la mélanisation de l’adrénaline. II Sur le sort de l’oxoadrénochrome au cours de la mélanisation de l’adrénaline. Structure des mélanines d’origine adrénalinique. Bull. soc. chim. biol. (Paris) 28, 104, 107 (1946).Google Scholar

Correia Alves, A.: Oxidation of Adrenaline by Iodate. Anais fac. farm. Porto 12, 79 (1952).Google Scholar

Correia Alves, A.: Oxidation of Adrenaline by Iodate. [Chem. Abstr. 48, 330 (1954)].Google Scholar

Dechamps, G., H. Le Bihan and C. Beaudet: Adrenochrome Mono-Semicarbazone Compound and Hemostatic Composition. U. S. Patent 2506294, 2 May 1950.Google Scholar

Derouaux, G.: Étude expérimentale de l’action hémostatique de l’adrénochrome. C. R. Séances Soc. Biol. 131, 830 (1939).Google Scholar

— Étude du mécanisme de l’action hémostatique de l’adrénaline. Arch. int. Pharmacodyn. 66, 202 (1941).Google Scholar

— Étude expérimentale de l’action hémostatique de la monoxime et de la mono-semicarbazone de l’adrénochrome. Étude de l’oxydation “in vitro” de l’adrénaline et d’autres amines diphénoliques par la phénoloxydase. Arch. int. Pharmacodyn. 69, 142, 205 (1943).Google Scholar

Drevon, B. et M. Stupfel: L’évolution des solutions aqueuses de l’adrénaline base soumise à l’action de l’oxyg è ne. C. R. Séances Soc. Biol. 143, 271 (1949).Google Scholar

Dulière, W. L. and H. S. Raper: The Tyrosinase-Tyrosine Reaction. VII. The Action of Tyrosinase on Certain Substances Related to Tyrosine. Biochemic. J. 24, 239 (1930).Google Scholar

Euler, U. S. v.: Noradrenaline. Springfield, Ill. Charles C. Thomas. 1956.Google Scholar

Euler, U. S. v. and U. Hamberg: Colorimetric Estimation of Noradrenalin in the Presence of Adrenalin. Science (Washington) 110, 561 (1949).CrossRefGoogle Scholar

Evans, W. S. and H. S. Raper: The Accumulation of l-3: 4-Dihydroxyphenyl-alanine in the Tyrosinase-Tyrosine Reaction. Biochemic. J. 31, 2162 (1937).Google Scholar

Fischer, P.: Sur la substance responsable de la fluorescence de l’adrénaline. Bull. soc. chim. Belges 58, 205 (1949).CrossRefGoogle Scholar

Fischer, P. et Z. M. Bacq: La fluorescence de l’adrénaline et de l’adrénochrome. C. R. Séances Soc. Biol. 143, 1159 (1949).Google Scholar

Fischer, P. et G. Derouaux: Étude du comportement de l’adrénochrome en présence des sels de Zn ou d’Al. C. R. Séances Soc. Biol. 144, 707 (1950).Google Scholar

Fischer, P., G. Derouaux, H. Lambot et J. Lecomte: Adrénochrome. Fluorescence et cations. Bull. soc. chim. Belges 59, 72 (1950).CrossRefGoogle Scholar

Fleischhacker, D. and N. Barsel: Adrenochrome Compositions. U. S. Patent 2581850, 8 January 1952.Google Scholar

— Adrenochrome Derivative and Process. U. S. Patent 2712024, 28 June 1955.Google Scholar

Fränkel, S. und R. Allers: Über eine neue charakteristische Adrenalinreaktion. Biochem. Z. 18, 40 (1909).Google Scholar

Friedenwald, J. S., H. Michel and W. Buschke: The Adrenochrome Redox System. Addendum. The Chemical Oxidation of Epinephrine to Adrenochrome and Higher Oxidation Products. Arch. Biochem. Biophys. 32, 382 (1951).CrossRefGoogle Scholar

Friedheim, E. A. H.: Atmungskatalyse durch ein natürliches Redoxsystem. Zwischenprodukt der Melaninbildung. Schweiz. med. Wschr. 65, 256 (1935) (spez. Fußnote)Google Scholar

Friedheim, E. A. H.: Atmungskatalyse durch ein natürliches Redoxsystem. Zwischenprodukt der Melaninbildung. vgl. Biochem. Z. 259, 257 (1933).Google Scholar

Gaddum, J. H. and H. Schild: A Sensitive Physical Test for Adrenaline. J. Physiol. 80, 9P (1934).Google Scholar

Green, D. E. and D. Richter: Adrenaline and Adrenochrome. Biochemic. J. 31, 596 (1937)Å·Google Scholar

Harley-Mason, J.: The Structure of Adrenochrome and its Reduction Products. Experientia 4, 307 (1948).CrossRefGoogle Scholar

— The Chemistry of Adrenochrome and its Derivatives. J. Chem. Soc. (London) 1950, 1276.Google Scholar

— Synthesis and Biosynthesis in the Indole Alkaloid Field. In: Recent Work on Naturally Occurring Nitrogen Heterocyclic Compounds. The Chemical Society, London, Special Publication No. 3, p. 45. 1955.Google Scholar

Harley-Mason, J. and J. D. Bu’Lock: Synthesis of 5: 6-Dihydroxyindole Derivatives: an Oxido-reduction Rearrangement Catalysed by Zinc Ions. Nature (London) 166, 1036 (1950).CrossRefGoogle Scholar

Heller, J. H., R. B. Setlow and E. Mylon: Fluorimetric Studies of Epinephrine and Arterenol. Amer. J. Physiol. 161, 268 (1950).Google Scholar

Hoffer, A., H. Osmond and J. Smythies: Schizophrenia: A New Approach. II. Result of a Year’s Research. J. Mental Sci. 100, 29 (1954).Google Scholar

Holtz, P. und G. Kroneberg: Über die Oxydation des Adrenalins und Arterenols (Adrenochrom und Nor-Adrenochrom). Biochem. Z. 320, 335 (1949/50).Google Scholar

Ingle, D. J., D. A. Shepherd and W. J. Haines: Effect of Adrenochrome upon Experimental Glycosuria in the Rat. J. Amer. Pharmaceut. Assoc. Sci. Ed. 37, 375 (1948).CrossRefGoogle Scholar

Kertész, D.: “Corps rouge” (Red Body) et Hallachrome. Experientia 6, 473 (1950).CrossRefGoogle Scholar

— Études sur la mélanogénèse: Sur l’existence des 5: 6-dihydroxyindoles comme produits intermédiaires essentiels pendant l’oxydation enzymatique de la tyrosine, de la dopa et de l’adrénaline. Bull. soc. chim. biol. (Paris) 35, 1157 (1953).Google Scholar

Kisch, B.: Metabolie Effects of Oxidized Suprarenin. Exp. Med. Surg. 5, 166 (1947).Google Scholar

Koelle, G. B. and J. S. Friedenwald: The Adrenochrome Redox System. Arch. Biochem. Biophys. 32, 370 (1951).CrossRefGoogle Scholar

Kuschinsky, G., U. Hille und H. Schimassek: Über Histamin als Mittler-Substanz bei der Wirkung von Adrenochrom auf die Blutungszeit. Arch. exper. Pathol. Pharmakol. 215, 48 (1952).Google Scholar

Lecomte, J. et P. Fischer: Action du trihydroxy-N-méthylindoIe sur le temps de saignement et la perméabilité capillaire. Arch. int. Pharmacodyn. 87, 225 (1951).Google Scholar

Loew, O.: Über die Natur der Giftwirkung des Suprarenins. Biochem. Z. 85, 295 (1918).Google Scholar

Lund, A.: Fluorimetric Determination of Adrenaline in Blood. I. Isolation of the Fluorescent Oxidation Product of Adrenaline; The Chemical Constitution of Adrenolutine; Simultaneous Fluorimetric Determinations of Adrenaline and Noradrenaline in Blood. Acta Pharm. Tox. 5, 75, 121 (1949)CrossRefGoogle Scholar

Lund, A.: Fluorimetric Determination of Adrenaline in Blood. I. Isolation of the Fluorescent Oxidation Product of Adrenaline; The Chemical Constitution of Adrenolutine; Simultaneous Fluorimetric Determinations of Adrenaline and Noradrenaline in Blood. Acta Pharm. Tox. 6, 137 (1950).CrossRefGoogle Scholar

Macciotta, E.: I prodotti di ossidazione dell’adrenalina. Gazz. chim. ital. 81, 485 (1951).Google Scholar

Marquardt, P.: Pharmakologie und Chemie der Adrenochrome. Z. ges. exp. Medizin 114, 112 (1944).CrossRefGoogle Scholar

— Die Auf-und Abbaustufen des Adrenalins (in ihrer Bedeutung für Pharmakologie und physiologische Chemie). Enzymologia 12, 166 (1946–48).Google Scholar

Mason, H. S.: The Chemistry of Melanin. III. Mechanism of the Oxidation of Dihydroxyphenylalanine by Tyrosinase. J. Biol. Chem. 172, 83 (1948).Google Scholar

Mazza, F. P. and G. Stolfi: Ricerche sul pigmento di Halla parthenopaea Costa. Arch. Sci. biol. 16, 182 (1931).Google Scholar

Oster, K. A.: Antipressor and Depressor Effects of Oxidation Products of Pressor Amines. Nature (London) 150, 289 (1942).CrossRefGoogle Scholar

Oster, K. A. and O. Martinez: Water Metabolism in Hypertensive Rats. J. exp. Medicine 78, 477 (1943).CrossRefGoogle Scholar

Oster, K. A. and H. Sobotka: Antipressor Effects of Orthoquinoid Epinephrine Derivatives in Experimental Hypertension in the Rat. J. Pharmacol. exp. Therapeut. 78, 100 (1943).Google Scholar

Persky, H.: Chemical Determination of Adrenaline and Noradrenaline in Body Fluids and Tissues. In: D. Glick, Methods of Biochemical Analysis, Vol.11, p. 57. New York: Interscience Publ. 1955.CrossRefGoogle Scholar

Ramirez, F. and P. v. Ostwalden: The Structure of Adrenochrome Monosemicarbazone. J. Organ. Chem. (USA) 20, 1676 (1955).CrossRefGoogle Scholar

Randall, L. O.: The Inhibition of the Anaerobic Glycolysis of Rat Brain by Adrenochrome. J. Biol. Chem. 165, 733 (1946).Google Scholar

Randall, L. O. and G. H. Hitchings: Effect of Tyrosinase on Phenylethylamine Derivatives. J. Pharmacol. exp. Therapeut. 146, 77 (1943).Google Scholar

Rangier, M.: Étapes intermédiaires au cours de la transformation de l’adrénaline en adrénochrome. C. R. hebd. Séances Acad. Sci. 220, 246 (1945).Google Scholar

Raper, H. S.: The Tyrosinase-Tyrosine Reaction. V. Production of l-3: 4-Di-hydroxyphenylalanine from Tyrosine; VI. Production from Tyrosine of 5: 6-Di-hydroxyindole and 5: 6-Dihydroxyindole-2-carboxylic Acid — the Precursor of Melanin. Biochemie. J. 20, 735 (1926)Google Scholar

Raper, H. S.: The Tyrosinase-Tyrosine Reaction. V. Production of l-3: 4-Di-hydroxyphenylalanine from Tyrosine; VI. Production from Tyrosine of 5: 6-Di-hydroxyindole and 5: 6-Dihydroxyindole-2-carboxylic Acid — the Precursor of Melanin. Biochemie. J. 21, 89 (1927).Google Scholar

Richter, D. and H. Blaschko: An Oxidation Product of Adrenaline. J. Chem. Soc. (London) 1937, 601.Google Scholar

Rinkel, M., R. W. Hyde, H. C. Solomon and H. Hoagland: Experimental Psychiatry. II. Clinical and Physico-chemical Observations in Experimental Psychosis. Amer. J. Psychiatr. 111, 881 (1955).Google Scholar

Rogister, Ch.: Dérivés colorés des amines sympathicomimétiques et hémostase spontanée. Arch. int. Pharmacodyn. 89, 28 (1952).Google Scholar

Roskam, J.: Le système nerveux adrénergique et l’action hémostatique des amines sympathicomimétiques, quinones et phénols. Acta phys. pharm. Néerland., num. dédié au Prof. Ten Cate (in press, 1957).Google Scholar

Roskam, J. et G. Derouaux: Hémostase spontanée et fonction sympathique. Bull. Soc. Med. 7, 227 (1942)Google Scholar

Roskam, J. et G. Derouaux: Interprétation de l’action hémostatique générale des substances sympathicomimétiques et théorie des transmissions neurohumorales. Arch. int. Pharmacodyn. 69, 348 (1944).Google Scholar

Roskam, J., G. Derouaux, L. Meys et L. Swalue: Un nouvel hémostatique biologique: la monosemicarbazone d’adrénochrome ou adrénoxyl. Arch. int. Pharmacodyn. 74, 162 (1947).Google Scholar

Ruiz-Gijon, J.: Preparation and Biological Activity of Adrenoerythrin (? Adrenalinquinone). Nature (London) 166, 831 (1951).CrossRefGoogle Scholar

Runti, C.S.: Un conveniente metodo di preparazione del monosemicarbazone dell’adrenochroma. Gazz. chim. ital. 80, 21 (1950).Google Scholar

Schayer, R. W.: Synthesis of dl-Adrenalin-β-C¹⁴ and dl-Adrenochrome-β-C¹⁴. J. Amer. Chem. Soc. 74, 2441 (1952).CrossRefGoogle Scholar

Sherber, D. A.: The Control of Bleeding. Amer. J. Surg. 86, 331 (1953).CrossRefGoogle Scholar

Snell, F. D. and C. T. Snell: Colorimetric Methods of Analysis, Vol. III, 3rd. Ed. New York: Van Nostrand. 1953.Google Scholar

Snyder, S. H., E. Leva and F. W. Oberst: An Evaluation of Adrenochrome and Iodoadrenochrome based on Blood Sugar Levels in Rabbits. J. Amer. Pharmaceut. Assoc. Sci. Ed. 36, 253 (1947).CrossRefGoogle Scholar

Sobotka, H.: Water-Soluble Monobetaine Hydrazones of the Aminochromes and Process of Preparing Same. U. S. Patents 2655510, 13 October 1953; 2726244, 6 December 1955.Google Scholar

Sobotka, H. and N. Adelman: Shortening of Bleeding Time by a Water-soluble Adrenochrome Derivative. Proc. Soc. exp. Biol. Med. 75, 789 (1950).Google Scholar

Sobotka, H. and J. Austin: Betaine Hydrazones of Aminochromes. J. Amer. Chem. Soc. 73, 3077 (1951).CrossRefGoogle Scholar

Société Belge de l’Azote et des Produits Chimiques du Marly: Procédé de préparation de dérivés hémostatiques stables de l’adrénochrome. Belg. Pat. 453374, 31 December 1943.Google Scholar

Sumpter, W. C. and F. M. Miller: Heterocyclic Compounds with Indole and Carbazole System. In: A. Weissberger, Chemistry of Heterocyclic Compounds, Vol. VIII. New York: Interscience Publ. 1954.CrossRefGoogle Scholar

Veer, W. L. C.: Melanin and its Precursors. II. On Adrenochrome. Rec. trav. chim. Pays-Bas 61, 638 (1942).CrossRefGoogle Scholar

Velluz, L.: Adrénochrome. In: Substances naturelles de synthèse, Vol. VI, p. 20. Paris: Masson. 1953.Google Scholar

Weinstein, S. and R. J. Manning: Intermediate Oxidation Products of Epinephrine. Proc. Soc. exp. Biol. Med. 32, 1096 (1934—35).Google Scholar

Wiesner, K.: Polarographische Untersuchung des Adrenochroms. Biochem. Z. 313, 48 (1942—43).Google Scholar

Witt, P. N.: Die Wirkung von Substanzen auf den Netzbau der Spinne als biologischer Test. Berlin: Lange und Springer. 1956.Google Scholar