The fumarate salts of the N -isopropyl- N -methyl derivatives of DMT and psilocin

The solid-state structures of the salts of two substituted tryptamines, namely N -isopropyl- N -methyltryptaminium (MiPT) fumarate {systematic name: [2-(1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate}, C 14 H 21 N 2 + ·C 4 H 3 O 4 − , and 4-hydroxy- N -isopropyl- N -methyltr...

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Bibliographic Details
Published in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2019-09, Vol.75 (9), p.1316-1320
Main Authors: Chadeayne, Andrew R., Pham, Duyen N. K., Golen, James A., Manke, David R.
Format: Article
Language:English
Subjects:
crystal structure
hydrogen bonding
Research Communications
tryptamines
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Summary:The solid-state structures of the salts of two substituted tryptamines, namely N -isopropyl- N -methyltryptaminium (MiPT) fumarate {systematic name: [2-(1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate}, C 14 H 21 N 2 + ·C 4 H 3 O 4 − , and 4-hydroxy- N -isopropyl- N -methyltryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4-hydroxy-1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate monohydrate}, C 14 H 21 N 2 O + ·C 4 H 3 O 4 − ·H 2 O, are reported. Both salts possess a protonated tryptammonium cation and a 3-carboxyacrylate (hydrogen fumarate) anion in the asymmetric unit; the 4-HO-MiPT structure also contains a water molecule of crystallization. Both cations feature disorder of the side chain over two orientations, in a 0.630 (3):0.370 (3) ratio for MiPT and a 0.775 (5):0.225 (5) ratio for 4-HO-MiPT. In both extended structures, N—H...O and O—H...O hydrogen bonds generate infinite two-dimensional networks.
ISSN:2056-9890
2056-9890
DOI:10.1107/S2056989019011253