5-Meth-oxy-<i>N</i>,<i>N</i>-di-<i>n</i>-propyl-tryptamine (5-MeO-DPT): freebase and fumarate.

Abstract

The solid-state structures of the synthetic psychedelic 5-meth-oxy-<i>N</i>,<i>N</i>-di-<i>n</i>-propyl-tryptamine (5-MeO-DPT) {systematic name: <i>N</i>-[2-(5-meth-oxy-1<i>H</i>-indol-3-yl)eth-yl]-<i>N</i>-propyl-propan-1-amine}, C₁₇H₂₅N₂O, and its fumarate salt, bis-(5-meth-oxy-<i>N</i>,<i>N</i>-di-<i>n</i>-propyl-tryptammonium) fumarate (systematic name: bis-{<i>N</i>-[2-(5-meth-oxy-1<i>H</i>-indol-3-yl)eth-yl]-<i>N</i>-propyl-propan-1-aminium} but-2-ene-dio-ate), 2C₁₇H₂₅N₂O⁺·C₄H₂O₄ ^2-, are reported. The freebase has a single tryptamine mol-ecule in the asymmetric unit. The mol-ecules 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 <i>R</i> ⁴ ₄(22) rings, and <i>C</i> ² ₂(14) and <i>C</i> ⁴ ₄(28) parallel chains along [001].

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