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. 2021 Apr 13;77(Pt 5):522-526.
doi: 10.1107/S2056989021003753. eCollection 2021 May 1.

5-Meth-oxy- N, N-di- n-propyl-tryptamine (5-MeO-DPT): freebase and fumarate

Duyen N K Pham  1 , Andrew R Chadeayne  2 , James A Golen  1 , David R Manke  1
Affiliations

5-Meth-oxy- N, N-di- n-propyl-tryptamine (5-MeO-DPT): freebase and fumarate

Duyen N K Pham et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The solid-state structures of the synthetic psychedelic 5-meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT) {systematic name: N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-propyl-propan-1-amine}, C17H25N2O, and its fumarate salt, bis-(5-meth-oxy-N,N-di-n-propyl-tryptammonium) fumarate (systematic name: bis-{N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-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 R 4 4(22) rings, and C 2 2(14) and C 4 4(28) parallel chains along [001].

Keywords: crystal structure; hydrogen bonding; indoles; tryptamines.

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Figures

Figure 1
Figure 1
The mol­ecular structures of 5-MeO-DPT freebase (left) and 5-MeO-DPT fumarate (right), showing the atomic labeling. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. Symmetry code: (i) 1 − x, 2 − y, 2 − z.
Figure 2
Figure 2
The crystal packing of 5-MeO-DPT freebase (left), viewed along the a axis, and the crystal packing of 5-MeO-DPT fumarate (right), viewed along the a axis. The hydrogen bonds (Tables 1 ▸ and 2 ▸) are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity.
Figure 3
Figure 3
The hydrogen-bonding network along [001], which consists of formula image(22) rings that are joined together by two parallel formula image(14) and formula image(28) chains. The three components described in graph-set notation and the combined chain is shown. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Hydrogen bonds are shown as dashed lines.
See this image and copyright information in PMC

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