Abstract
The class of cyclic oxidation products of phenylethyl amines with carbonyl groups in position 5 and 6 of a dihydroindole system and including variants in the heterocyclic moiety has been designated 1951 as “Aminochromes” (92). We have coined this term as a shorthand description of these compounds.
The terms adrenaline and epinephrine are used interchangeably throughout this review.
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References
Anderson, A.B.: Inactivation of Serum Alkaline Phosphatase by Adrenaline and Related Substances. Biochemic. J. 45, xxxvi (1949).
Austin, J., J. D. Chanley and H. Sobotka: The Rearrangement of Epinochrome. J. Amer. Chem. Soc. 73, 2395 (1951).
H. Sobotka — Hydrogenation of Epinochrome. J. Amer. Chem. Soc. 73, 5299 (1951).
Bacq, Z. M.: La semicarbazone de l’adrénochrome. C. R. Séances Soc. Biol. 141, 536 (1947)
Bacq, Z. M. et P. Fischer: Sur l’existence de l’adrénaline-quinone. Arch. int. Physiol. 57, 271 (1949–50).
Ball, E. G. and T. T. Chen: Studies on Oxidation-Reduction. XX. Epinephrine and Related Compounds. J. Biol. Chem. 102, 691 (1933).
Barer, R., H. Blaschko and H. Langemann: Iodochromes of Substances Related to Adrenaline. J. Physiol. 112, 21P (1951).
Barsel, N.: Therapeutic Complexes. U. S. Patent 2691662, 12 October (1954).
— Adrenochrome Isonicotinic Acid Hydrazone. U. S. Patent 2728772, 27 December 1955.
Beaudet, C.: Activité optique des produits de réduction de l’adrénochrome. Experientia 6, 186 (1950).
— Substances nouvelles apparentées à l’adrénochrome. Experientia 7, 291 (1951).
Beaudet, C., F. Debot, H. Lambot et J. Toussaint: La monosemicarbazone de l’adrénochrome. Experientia 7, 293 (1951).
Bergel, F. and A. L. Morrison: The Oxidation of Adrenaline. J. Chem. Soc. (London) 1943, 48.
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).
Braconier, F., H. Le Bihan et C. Beaudet: L’adrénochrome et ses dérivés. Arch. int. Pharmacodyn. 69, 181 (1943).
Buchnea, D.: Adrenochrome (Reported by C. L. McCarthy). Report No. 47, Off. Pub. Board, Dept. Coram., Washington, D. C. (1945).
Bu’Lock, J. D. and J. Harley-Mason: The Chemistry of Adrenochrome. II. Some Analogues and Derivatives. J. Chem. Soc. (London) 1951, 712.
— Melanin and its Precursors. III. New Syntheses of 5: 6-Dihydroxyindole and its Derivatives. J. Chem. Soc. (London) 1951, 2248.
Bu’Lock, J. D., J. Harley-Mason and H. S. Mason: Hallachrome and Dopachrome. Biochemic. J. 47, xxxii (1950).
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.
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).
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).
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).
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).
Chanley, J. D., N. Barsel and H. Sobotka: Unpublished observations.
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).
Correia Alves, A.: Oxidation of Adrenaline by Iodate. Anais fac. farm. Porto 12, 79 (1952).
Correia Alves, A.: Oxidation of Adrenaline by Iodate. [Chem. Abstr. 48, 330 (1954)].
Dechamps, G., H. Le Bihan and C. Beaudet: Adrenochrome Mono-Semicarbazone Compound and Hemostatic Composition. U. S. Patent 2506294, 2 May 1950.
Derouaux, G.: Étude expérimentale de l’action hémostatique de l’adrénochrome. C. R. Séances Soc. Biol. 131, 830 (1939).
— Étude du mécanisme de l’action hémostatique de l’adrénaline. Arch. int. Pharmacodyn. 66, 202 (1941).
— 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).
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).
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).
Euler, U. S. v.: Noradrenaline. Springfield, Ill. Charles C. Thomas. 1956.
Euler, U. S. v. and U. Hamberg: Colorimetric Estimation of Noradrenalin in the Presence of Adrenalin. Science (Washington) 110, 561 (1949).
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).
Fischer, P.: Sur la substance responsable de la fluorescence de l’adrénaline. Bull. soc. chim. Belges 58, 205 (1949).
Fischer, P. et Z. M. Bacq: La fluorescence de l’adrénaline et de l’adrénochrome. C. R. Séances Soc. Biol. 143, 1159 (1949).
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).
Fischer, P., G. Derouaux, H. Lambot et J. Lecomte: Adrénochrome. Fluorescence et cations. Bull. soc. chim. Belges 59, 72 (1950).
Fleischhacker, D. and N. Barsel: Adrenochrome Compositions. U. S. Patent 2581850, 8 January 1952.
— Adrenochrome Derivative and Process. U. S. Patent 2712024, 28 June 1955.
Fränkel, S. und R. Allers: Über eine neue charakteristische Adrenalinreaktion. Biochem. Z. 18, 40 (1909).
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).
Friedheim, E. A. H.: Atmungskatalyse durch ein natürliches Redoxsystem. Zwischenprodukt der Melaninbildung. Schweiz. med. Wschr. 65, 256 (1935) (spez. Fußnote)
Friedheim, E. A. H.: Atmungskatalyse durch ein natürliches Redoxsystem. Zwischenprodukt der Melaninbildung. vgl. Biochem. Z. 259, 257 (1933).
Gaddum, J. H. and H. Schild: A Sensitive Physical Test for Adrenaline. J. Physiol. 80, 9P (1934).
Green, D. E. and D. Richter: Adrenaline and Adrenochrome. Biochemic. J. 31, 596 (1937)Å·
Harley-Mason, J.: The Structure of Adrenochrome and its Reduction Products. Experientia 4, 307 (1948).
— The Chemistry of Adrenochrome and its Derivatives. J. Chem. Soc. (London) 1950, 1276.
— 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.
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).
Heller, J. H., R. B. Setlow and E. Mylon: Fluorimetric Studies of Epinephrine and Arterenol. Amer. J. Physiol. 161, 268 (1950).
Hoffer, A., H. Osmond and J. Smythies: Schizophrenia: A New Approach. II. Result of a Year’s Research. J. Mental Sci. 100, 29 (1954).
Holtz, P. und G. Kroneberg: Über die Oxydation des Adrenalins und Arterenols (Adrenochrom und Nor-Adrenochrom). Biochem. Z. 320, 335 (1949/50).
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).
Kertész, D.: “Corps rouge” (Red Body) et Hallachrome. Experientia 6, 473 (1950).
— 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).
Kisch, B.: Metabolie Effects of Oxidized Suprarenin. Exp. Med. Surg. 5, 166 (1947).
Koelle, G. B. and J. S. Friedenwald: The Adrenochrome Redox System. Arch. Biochem. Biophys. 32, 370 (1951).
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).
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).
Loew, O.: Über die Natur der Giftwirkung des Suprarenins. Biochem. Z. 85, 295 (1918).
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)
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).
Macciotta, E.: I prodotti di ossidazione dell’adrenalina. Gazz. chim. ital. 81, 485 (1951).
Marquardt, P.: Pharmakologie und Chemie der Adrenochrome. Z. ges. exp. Medizin 114, 112 (1944).
— Die Auf-und Abbaustufen des Adrenalins (in ihrer Bedeutung für Pharmakologie und physiologische Chemie). Enzymologia 12, 166 (1946–48).
Mason, H. S.: The Chemistry of Melanin. III. Mechanism of the Oxidation of Dihydroxyphenylalanine by Tyrosinase. J. Biol. Chem. 172, 83 (1948).
Mazza, F. P. and G. Stolfi: Ricerche sul pigmento di Halla parthenopaea Costa. Arch. Sci. biol. 16, 182 (1931).
Oster, K. A.: Antipressor and Depressor Effects of Oxidation Products of Pressor Amines. Nature (London) 150, 289 (1942).
Oster, K. A. and O. Martinez: Water Metabolism in Hypertensive Rats. J. exp. Medicine 78, 477 (1943).
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).
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.
Ramirez, F. and P. v. Ostwalden: The Structure of Adrenochrome Monosemicarbazone. J. Organ. Chem. (USA) 20, 1676 (1955).
Randall, L. O.: The Inhibition of the Anaerobic Glycolysis of Rat Brain by Adrenochrome. J. Biol. Chem. 165, 733 (1946).
Randall, L. O. and G. H. Hitchings: Effect of Tyrosinase on Phenylethylamine Derivatives. J. Pharmacol. exp. Therapeut. 146, 77 (1943).
Rangier, M.: Étapes intermédiaires au cours de la transformation de l’adrénaline en adrénochrome. C. R. hebd. Séances Acad. Sci. 220, 246 (1945).
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)
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).
Richter, D. and H. Blaschko: An Oxidation Product of Adrenaline. J. Chem. Soc. (London) 1937, 601.
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).
Rogister, Ch.: Dérivés colorés des amines sympathicomimétiques et hémostase spontanée. Arch. int. Pharmacodyn. 89, 28 (1952).
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).
Roskam, J. et G. Derouaux: Hémostase spontanée et fonction sympathique. Bull. Soc. Med. 7, 227 (1942)
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).
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).
Ruiz-Gijon, J.: Preparation and Biological Activity of Adrenoerythrin (? Adrenalinquinone). Nature (London) 166, 831 (1951).
Runti, C.S.: Un conveniente metodo di preparazione del monosemicarbazone dell’adrenochroma. Gazz. chim. ital. 80, 21 (1950).
Schayer, R. W.: Synthesis of dl-Adrenalin-β-C14 and dl-Adrenochrome-β-C14. J. Amer. Chem. Soc. 74, 2441 (1952).
Sherber, D. A.: The Control of Bleeding. Amer. J. Surg. 86, 331 (1953).
Snell, F. D. and C. T. Snell: Colorimetric Methods of Analysis, Vol. III, 3rd. Ed. New York: Van Nostrand. 1953.
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).
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.
Sobotka, H. and N. Adelman: Shortening of Bleeding Time by a Water-soluble Adrenochrome Derivative. Proc. Soc. exp. Biol. Med. 75, 789 (1950).
Sobotka, H. and J. Austin: Betaine Hydrazones of Aminochromes. J. Amer. Chem. Soc. 73, 3077 (1951).
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.
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.
Veer, W. L. C.: Melanin and its Precursors. II. On Adrenochrome. Rec. trav. chim. Pays-Bas 61, 638 (1942).
Velluz, L.: Adrénochrome. In: Substances naturelles de synthèse, Vol. VI, p. 20. Paris: Masson. 1953.
Weinstein, S. and R. J. Manning: Intermediate Oxidation Products of Epinephrine. Proc. Soc. exp. Biol. Med. 32, 1096 (1934—35).
Wiesner, K.: Polarographische Untersuchung des Adrenochroms. Biochem. Z. 313, 48 (1942—43).
Witt, P. N.: Die Wirkung von Substanzen auf den Netzbau der Spinne als biologischer Test. Berlin: Lange und Springer. 1956.
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Sobotka, H., Barsel, N., Chanley, J.D. (1957). The Aminochromes.. In: Zechmeister, L. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles, vol 14. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7164-6_5
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