Photoinduced oxidation of tryptamine derivatives. Formation of pyrrolo[2,3-b]indole and N b-(4-cyanobutadienyl)tryptamine

Irradiation (253·7 nm) of NaNb-dimethyltryptamine with pyridine N-oxide produced 1,8-dimethyl-3a-hydroxy-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole (4), whilst with visible light Nb-(4-cyanobutadienyl)-NaNb-dimethyltryptamine (5) was obtained.