5-Methoxy-N,N-di-n-propyltryptamine (5-MeO-DPT): freebase and fumarate
Duyen N. K. Pham, A.r. Chadeayne, James A. Golen, David R. Manke
Acta Crystallographica Section E Crystallographic Communications April 13, 2021 DOI: 10.1107/s2056989021003753 via OpenAlex
Summary
AI-generated from the abstractThe solid-state structures of the synthetic psychedelic 5-MeO-DPT and its fumarate salt are reported. The freebase forms zigzag chains linked by N—H...N hydrogen bonds along one crystal direction. The fumarate salt contains tryptammonium cations and fumarate dianions held together in one-dimensional chains by N—H...O hydrogen bonds, forming specific ring and chain patterns.
Study at a glance
| Characteristics | Structural chemistry report Peer reviewed |
|---|---|
| Keywords | Stereochemistry Medicinal chemistry |
| Citations | 3 |
| Key finding | The freebase of 5-MeO-DPT forms N—H...N hydrogen-bonded zigzag chains, while its fumarate salt forms N—H...O hydrogen-bonded one-dimensional chains with characteristic ring and chain motifs. |
Abstract
The solid-state structures of the synthetic psychedelic 5-methoxy- N , N -di- n -propyltryptamine (5-MeO-DPT) {systematic name: N -[2-(5-methoxy-1 H -indol-3-yl)ethyl]- N -propylpropan-1-amine}, C 17 H 25 N 2 O, and its fumarate salt, bis(5-methoxy- N , N -di- n -propyltryptammonium) fumarate (systematic name: bis{ N -[2-(5-methoxy-1 H -indol-3-yl)ethyl]- N -propylpropan-1-aminium} but-2-enedioate), 2C 17 H 25 N 2 O + ·C 4 H 2 O 4 2− , are reported. The freebase has a single tryptamine molecule in the asymmetric unit. The molecules are linked together by N—H...N hydrogen bonds in zigzag chains along the [010] direction. The fumarate salt has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N—H...O hydrogen bonds. These chains are combinations of R 4 4 (22) rings, and C 2 2 (14) and C 4 4 (28) parallel chains along [001].