Syntheses and structures of two norpsilocin derivatives: N-ethyl-4-hy-droxy-tryptamine (4-HO-NET) and 4-hy-droxy-N-propyl-tryptamine (4-HO-NPT).

The solid-state structures of N-ethyl-4-hy-droxy-tryptamine (4-HO-NET) {systematic name: 3-[2-(ethyl-amino)-eth-yl]-1H-indol-4-ol}, C12H16N2O, and 4-hy-droxy-N-propyl-tryptamine (4-HO-NPT) {systematic name: 3-[2-(propyl-amino)-eth-yl]-1H-indol-4-ol}, C13H18N2O, are reported. Both compounds possess a single tryptamine mol-ecule in the asymmetric unit that exhibits an inter-nal O-H⋯N hydrogen bond. In the extended structures, the mol-ecules are linked by N-H⋯O hydrogen bonds to form infinite chains along [001] for 4-HO-NET and along [101] for 4-HO-NPT.