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. 2020 Jul 3;76(Pt 8):1201-1205.
doi: 10.1107/S2056989020008683. eCollection 2020 Aug 1.

DMT analogues: N-ethyl- N-propyl-tryptamine and N-allyl- N-methytryptamine as their hydro-fumarate salts

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

DMT analogues: N-ethyl- N-propyl-tryptamine and N-allyl- N-methytryptamine as their hydro-fumarate salts

Andrew R Chadeayne et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The solid-state structures of the hydro-fumarate salts of two N,N-di-alkyl-tryptamines, namely N-ethyl-N-propyl-tryptammonium (EPT) hydro-fumarate {systematic name: [2-(1H-indol-3-yl)eth-yl](meth-yl)propyl-aza-nium 3-carb-oxy-prop-2-enoate}, C15H23N2 +·C4H3O4 -, and N-allyl-N-methyl-tryptammonium (MALT) hydro-fumarate {systematic name: [2-(1H-indol-3-yl)eth-yl](meth-yl)(prop-2-en-1-yl)aza-nium 3-carb-oxy-prop-2-enoate}, C14H19N2 +·C4H3O4 -, are reported. Both compounds possess a protonated tryptammonium cation, and a hydro-fumarate anion in the asymmetric unit. The ethyl group of the EPT cation is modeled as a two-component disorder with 50% occupancy for each component. In the extended structure, N-H⋯O and O-H⋯O hydrogen bonds generate infinite two-dimensional networks parallel to the (001) plane for both compounds.

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

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Figures

Figure 1
Figure 1
The asymmetric unit of N-ethyl-N-propyl­tryptammonium hydro­fumarate showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. Dashed bonds indicate the disordered component of the structure. The hydrogen bond is shown by a dashed line.
Figure 2
Figure 2
The asymmetric unit of N-methyl-N-allyl­tryptammonium hydro­fumarate showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. The hydrogen bond is shown by a dashed line.
Figure 3
Figure 3
The hydrogen bonding of a hydro­fumarate ion in the structure of N-ethyl-N-propyl­tryptammonium hydro­fumarate, with hydrogen bonds shown as dashed lines. Only one component of the disorder is shown, and hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Symmetry codes: (i) 1 + x, y, z; (iv) −1 + x, y, z; (v) 2 − x, −formula image + y, 1 − z.
Figure 4
Figure 4
The hydrogen bonding of a hydro­fumarate ion in the structure of N-methyl-N-allyl­tryptammonium hydro­fumarate, with hydrogen bonds shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Symmetry codes: (i) x − 1, y, z; (iv) 1 + x, y, z; (v) 1 − x, formula image + y, formula image − z; (vi) −x, formula image + y, formula image − z.
See this image and copyright information in PMC

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