Heacock, R. A., The Aminochromes

The higher decomposition points were obtained when adrenochrome methyl and ethyl ethers were prepared by oxidation of the appropriate catecholamine in methanol with silver oxide. The BOlid aminochromes were then obtained as microcrystalline solids on addition of dry ether and cooling the resultant solution to — 80°. The slightly less pure products were obtained when the oxidation was carried out in acetonitrile. [R. A. Heacock and B. D. Scott, loc. cit. (footnote c )]. 

A It has recently been shown that the iodo-(or bromo-)aminochromes should be formulated as 7-iodo (or 7-bromo) derivatives [R. A. Heacock, O. Hutzinger, B. D. Scott, J. W. Daly, and B. Witkop, J. Am. Chem, Soc. 85, 1825 (1963)] consequently, all such compounds are described in this manner throughout this review. 

The rates obtained for noradrenochrome were not as reliable as those for the other aminochromes due to the difficulties experienced in obtaining pure solutions of noradrenochrome [cf. R. A. Heacock and G. L. Mattok, loc. cit. (footnote a )]. 

Frederick Kurzer The Aminochromes R. A. Heacock Aromatic Quinolizines B. S. Thyagarajan Advances in Pyrrolizidine Chemistry... 

Aminochromes, Family of highly colored 2,3-di-hydfoindole-5,6-quinones obtained by oxidaiive cydization of catecholamines Sobotka, Austin J Am. Chem. Soc. 73, 3077 (1951), Best represented by a zwitteriomc structure with the substituents determined by the catecholamine used e g- for epinephrine as starting material, R — CH3, R = H and R" = OH, Reviews Sobotka et ai, Fortschr. Chem. Org, Natursj. 14, 217 (1957) Heacock. Advan. Heterocyci Chem- 5, 205 (1965) Heacock, Powell. Progr, Med. Chem. 9, 275 (1972). 

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