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The solid-state structures of the salts of two substituted tryptamines, namely N -isopropyl- N -methyl-tryptaminium (MiPT) fumarate {systematic name: [2-(1 H -indol-3-yl)eth-yl](meth-yl)propan-2-yl-aza-nium 3-carb-oxy-prop-2-enoate}, C 14 H 21 N 2  + ·C 4 H 3 O 4  - , and 4-hy-droxy- N -isopropyl- N -methyl-tryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4-hy-droxy-1 H -indol-3-yl)eth-yl](meth-yl)propan-2-yl-aza-nium 3-carb-oxy-prop-2-enoate monohydrate}, C 14 H 21 N 2 O + ·C 4 H 3 O 4  - ·H 2 O, are reported. Both salts possess a proton-ated tryptammonium cation and a 3-carb-oxy-acrylate (hydrogen fumarate) anion in the asymmetric unit; the 4-HO-MiPT structure also contains a water mol-ecule of crystallization. Both cations feature disorder of the side chain over two orientations, in a 0.630 (3):0.370 (3) ratio for MiPT and a 0.775 (5):0.225 (5) ratio for 4-HO-MiPT. In both extended structures, N-H⋯O and O-H⋯O hydrogen bonds generate infinite two-dimensional networks.

The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin