The methanol and ethanol solvates of 4-glutarato-N,N-diisopropyltryptamine

Abstract

The solid-state structures of two solvated forms of 4-glutarato-N,N-diisopropyltryptamine were determined by single-crystal X-ray diffraction, namely, 5-[(3-{2-[bis(propan-2-yl)azaniumyl]ethyl}-1H-indol-4-yl)oxy]-5-oxopentanoate methanol monosolvate, C21H30N2O4·CH3OH, and the analogous ethanol monosolvate, C21H30N2O4·C2H6O. In both compounds, the 4-glutarato-N,N-diisopropyltryptamine exists as a zwitterion with a protonated tertiary ammonium and a deprotonated glutarato carboxylate. The tryptamine zwitterions and alcohol solvates in both structures combine to produce near identical hydrogen-bonding networks, with N—H...O and O—H...O hydrogen bonds joining the molecules together in two-dimensional networks parallel to the (100) plane.

Keywords

• crystal structure
• tryptamines
• indoles
• zwitterions
• hydrogen bonds