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

The solid-state structures of the salts of two substituted tryptamines, namely N-isopropyl-N-methyl­tryptaminium (MiPT) fumarate {systematic name: [2-(1H-indol-3-yl)eth­yl](meth­yl)propan-2-yl­aza­nium 3-carb­oxy­prop-2-enoate}, C(14)H(21)N(2) (+)·C(4)H(3)O(4) (−), and 4-hy­droxy-N-isopropyl-N-methyl­tryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4-hy­droxy-1H-indol-3-yl)eth­yl](meth­yl)propan-2-yl­aza­nium 3-carb­oxy­prop-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 proton­ated tryptammonium cation and a 3-carb­oxy­acrylate (hydrogen fumarate) anion in the asymmetric unit; the 4-HO-MiPT structure also contains a water mol­ecule 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.