Crystal structures of new psychoactive substances 4-HO-DET and 4-AcO-DET.

The solid-state structures of 4-hy-droxy-N,N-di-ethyl-tryptammonium (4-HO-DET) hydro-fumarate {systematic name: dieth-yl[2-(4-hy-droxy-1H-indol-3-yl)eth-yl]aza-nium 3-carb-oxy-prop-2-enoate}, C14H21N2O+·C4H3O4 -, and 4-acet-oxy-N,N-di-ethyl-tryptammonium (4-AcO-DET) fumarate/fumaric acid {systematic name: bis-{[2-(4-acet-oxy-1H-indol-3-yl)eth-yl]di-ethyl-aza-nium} but-2-ene-dio-ate-(E)-butenedioic acid (1/1)}, 2C16H23N2O2+·C4H2O4 2-·C4H4O4, were determined by single-crystal X-ray diffraction. The 4-HO-DET structure exhibits a single tryptammonium cation and a single hydro-fumarate anion in the asymmetric unit. The ions are joined together by N-H⋯O and O-H⋯O hydrogen bonds in two-dimensional sheets lying in the (001) plane. The 4-AcO-DET structure exhibits a single tryptammonium cation, half of a fumarate dianion and half of a fumaric acid mol-ecule in the asymmetric unit. The ions and mol-ecules are joined together by N-H⋯O and O-H⋯O hydrogen bonds in an infinite three-dimensional network.