'Foxtrot' fumarate: a water-soluble salt of N,N-diallyl-5-methoxytryptamine (5-MeO-DALT)

The synthesis and solid-state structure of the fumarate salt of the synthetic psychedelic 5-meth­oxy-N,N-di­allyl­tryptamine (5-MeO-DALT) is reported.
The title compound, bis­(N,N-diallyl-5-meth­oxy­tryptammonium) (5-MeO-DALT) fumarate (systematic name: bis­{N-[2-(5-meth­oxy-1H-indol-3-yl)eth­yl]- N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-but-2-enedioate), 2C17H23N2O+·C4H2O4 2−, has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N—H⋯O hydrogen bonds. These chains are combinations of R 4 4(22) rings, and C 2 2(14) and C 4 4(28) parallel chains along [111].