2,5-Di­methyl­bufo­tenine and 2,5-di­methyl­bufo­teni­dine: novel derivatives of natural tryptamines found in Bufo alvarius toads

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-1H-indol-3-yl)eth­yl]di­methyl­aza­nium} (2E)-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-1H-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-1H-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.