Syntheses and structures of two norpsilocin derivatives: <i>N</i>-ethyl-4-hy-droxy-tryptamine (4-HO-NET) and 4-hy-droxy-<i>N</i>-propyl-tryptamine (4-HO-NPT).
Abstract
The solid-state structures of <i>N</i>-ethyl-4-hy-droxy-tryptamine (4-HO-NET) {systematic name: 3-[2-(ethyl-amino)-eth-yl]-1<i>H</i>-indol-4-ol}, C<sub>12</sub>H<sub>16</sub>N<sub>2</sub>O, and 4-hy-droxy-<i>N</i>-propyl-tryptamine (4-HO-NPT) {systematic name: 3-[2-(propyl-amino)-eth-yl]-1<i>H</i>-indol-4-ol}, C<sub>13</sub>H<sub>18</sub>N<sub>2</sub>O, 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.
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