174. Adrenolutin

Nomenclature

CAS number: 642-75-1
1-Methyl-1H-indole-3,5,6-triol; N-methyl-5,6-dihydroxyindoxyl; 3,5,6-trihydroxy-N-methylindole.
C9H9NO3; mol wt 179.17.
C 60.33%, H 5.06%, N 7.82%, O 26.79%.

Description and references

Alkaline rearrangement product of adrenochrome. Isoln and identification: Lund, Acta Pharmacol. Toxicol. 5, 75 (1949). Structure and synthesis: Balsinger et al., Helv. Chim. Acta 36, 708 (1953); Heacock, Mahon, Can. J. Chem. 36, 1550 (1958). NMR studies and its existence in the ketonic form in solution: Powell, Heacock, Chim. Ther. 7, 133 (1972).

Chemical structure

Properties

Monohydrate, bright yellow prisms from water, mp 236° (dec); mp 195° (Balsinger). Anhydrous, bright yellow prisms, mp 245°.