Bis(4-acet-oxy- N, N-di-methyl-tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug

Abstract

The title compound (systematic name: bis-{2-[4-(acet-yloxy)-1H-indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C₁₄H₁₉N₂O₂ ⁺·C₄H₂O₄ ^2-, has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N-H⋯O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N-H⋯O hydrogen bonds between the indole H atoms and the fumarate O atoms. The hydrogen bonds hold the ions together in infinite one-dimensional chains along [111].

Keywords: crystal structure; hydrogen bonding; tryptamines.

Figure 1

The mol­ecular structure of bis­(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate, showing the atomic labeling. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. Symmetry code: (i) 2 − x, 1 − y, 2 − z.

Figure 2

The hydrogen bonding of the fumarate ion in the structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity. Symmetry codes: (i) 2 − x, 1 − y, 2 − z, (iii) 1 − x, 1 + y, 1 + z, (iv) 1 − x, −y, 1 − z.

Figure 3

The crystal packing of the title compound, viewed along the b axis. The N—H⋯O bonds (Table 1 ▸) are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity