5-Meth­oxy-N,N-di-n-propyl­tryptamine (5-MeO-DPT): freebase and fumarate

The solid-state structures of the synthetic psychedelic 5-meth­oxy-N,N-di-n-propyl­tryptamine (5-MeO-DPT) {systematic name: N-[2-(5-meth­oxy-1H-indol-3-yl)eth­yl]-N-propyl­propan-1-amine}, C(17)H(25)N(2)O, and its fumarate salt, bis­(5-meth­oxy-N,N-di-n-propyl­tryptammonium) fumarate (systematic name: bis­{N-[2-(5-meth­oxy-1H-indol-3-yl)eth­yl]-N-propyl­propan-1-aminium} but-2-ene­dio­ate), 2C(17)H(25)N(2)O(+)·C(4)H(2)O(4) (2−), are reported. The freebase has a single tryptamine mol­ecule in the asymmetric unit. The mol­ecules are linked together by N—H⋯N hydrogen bonds in zigzag chains along the [010] direction. The fumarate salt 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 [001].