The solid state structures of two synthetic N-monoalkytryptamine analogs of the ‘magic’ mushroom natural product norpsilocin are presented. The solid-state structures of N-ethyl-4-hydroxytryptamine (4-HO-NET) systematic name: 3-[2-(ethylamino)ethyl]-1H-indol-4-ol, C12H16N2O, and 4-hydroxy-N-propyltryptamine (4-HO-NPT) systematic name: 3-[2-(propylamino)ethyl]-1H-indol-4-ol, C13H18N2O, are reported. Both compounds possess a single tryptamine molecule in the asymmetric unit that exhibits an internal O—H⋯N hydrogen bond. In the extended structures, the molecules 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.
- Syntheses and structures of two norpsilocin derivatives: N-ethyl-4-hydroxytryptamine (4-HO-NET) and 4-hydroxy-N-propyltryptamine (4-HO-NPT)
- Marilyn Naeem - University of Massachusetts DartmouthAndrew R. Chadeayne - Sunset Laboratory (United States)James A. Golen - University of Massachusetts DartmouthDavid R. Manke - University of Massachusetts Dartmouth
- Acta crystallographica. Section E, Crystallographic communications, Vol.82(Pt 9), pp.1082-1086
- International Union of Crystallography
- 5
- Department of Chemistry and Biochemistry
- English
- Journal article
- https://doi.org/10.1107/S2056989026008571
- 9914553188501301