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).
Marilyn Naeem, Andrew R Chadeayne, James A. Golen, David R. Manke
Acta crystallographica. Section E, Crystallographic communications September 1, 2026 DOI: 10.1107/s2056989026008571 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Crystallographic structure determination Peer reviewed |
|---|---|
| Keywords | Crystal structure Hydrogen bonds Indoles Tryptamines |
| Key points | Both 4-HO-NET and 4-HO-NPT crystallize with a single tryptamine molecule in the asymmetric unit, each featuring an internal O-H...N hydrogen bond. Intermolecular N-H...O hydrogen bonds link the molecules into infinite chains along [001] for 4-HO-NET and along [101] for 4-HO-NPT. |
Abstract
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.