2,5-Di-methyl-bufo-tenine and 2,5-di-methyl-bufo-teni-dine: novel derivatives of natural tryptamines found in Bufo alvarius toads.

The solid-state structure of the bufotenine derivative bis-(5-meth-oxy-2,N,N-tri-methyl-tryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis-{[2-(5-meth-oxy-2-methyl-1H-indol-3-yl)eth-yl]di-methyl-aza-nium} (2E)-but-2-enedioate), 2C(14)H(21)N(2)O(+)·C(4)H(2)O(4) (2-), the bufotenidine derivative 5-meth-oxy-2,N,N,N-tetra-methyl-tryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-meth-oxy-2-methyl-1H-indol-3-yl)eth-yl]tri-methyl-aza-nium iodide}, C(15)H(23)N(2)O(+)·I(-), and the hydrate of the same {systematic name: [2-(5-meth-oxy-2-methyl-1H-indol-3-yl)eth-yl]tri-methyl-aza-nium 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 inter-actions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water mol-ecule in the asymmetric unit. It shows N-H⋯I and O-H⋯I hydrogen bonds that couple the tryptammonium cations into dimers.