2,5-Dimethylbufotenine and 2,5-dimethylbufotenidine: novel derivatives of natural tryptamines found in Bufo alvarius toads
Duyen N. K. Pham, A.r. Chadeayne, James A. Golen, David R. Manke
Acta Crystallographica Section E Crystallographic Communications January 29, 2021 DOI: 10.1107/s2056989021000803 via OpenAlex
Summary
AI-generated from the abstractThe solid-state structures of three tryptamine derivatives—a bufotenine derivative (5-MeO-2-Me-DMT fumarate), a bufotenidine derivative (5-MeO-2-Me-TMT iodide), and its hydrate—were determined. The fumarate salt forms two-dimensional networks through N—H...O hydrogen bonds. The iodide salt shows N—H...I hydrogen bonds and π–π interactions linking indole dimers. The hydrate exhibits N—H...I and O—H...I hydrogen bonds that couple cations into dimers. These structural details are relevant for understanding the molecular interactions of psychedelic tryptamines.
Study at a glance
| Characteristics | Crystallographic study Peer reviewed |
|---|---|
| Keywords | Hydrogen bond Hydrate Methyl iodide Medicinal chemistry Molecule |
| Citations | 7 |
| Key finding | The three tryptamine derivatives form distinct hydrogen-bond networks and π–π interactions in their crystal structures. |
Abstract
The solid-state structure of the bufotenine derivative bis(5-methoxy-2, N , N -trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1 H -indol-3-yl)ethyl]dimethylazanium} (2 E )-but-2-enedioate), 2C 14 H 21 N 2 O + ·C 4 H 2 O 4 2− , the bufotenidine derivative 5-methoxy-2, N , N , N -tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-methoxy-2-methyl-1 H -indol-3-yl)ethyl]trimethylazanium iodide}, C 15 H 23 N 2 O + ·I − , and the hydrate of the same {systematic name: [2-(5-methoxy-2-methyl-1 H -indol-3-yl)ethyl]trimethylazanium iodide monohydrate}, C 15 H 23 N 2 O + ·I − ·H 2 O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N—H...O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked via N—H...I hydrogen bonds, and indoles are coupled in dimers through π–π interactions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water molecule in the asymmetric unit. It shows N—H...I and O—H...I hydrogen bonds that couple the tryptammonium cations into dimers.