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
Summary
The solid-state structures of two bufotenine derivatives reveal intricate molecular interactions. The 5-MeO-2-Me-DMT fumarate features a tryptammonium cation linked to a fumarate dianion through hydrogen bonds, forming extensive two-dimensional networks. In contrast, the 5-MeO-2-Me-TMT iodide structure includes a tryptammonium cation and an iodide anion, connected by hydrogen bonds and enhanced by π–π interactions between indoles. Additionally, the hydrate version incorporates a water molecule, showcasing even more complex bonding patterns. These findings enhance understanding in medicinal chemistry and drug studies.
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.