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. 2020 Jul 24;76(Pt 8):1357-1360.
doi: 10.1107/S2056989020010014. eCollection 2020 Aug 1.

Quaternary tryptammonium salts: N, N-dimethyl- N- n-propyl-tryptammonium (DMPT) iodide and N-allyl- N, N-di-methyl-tryptammonium (DMALT) iodide

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

Quaternary tryptammonium salts: N, N-dimethyl- N- n-propyl-tryptammonium (DMPT) iodide and N-allyl- N, N-di-methyl-tryptammonium (DMALT) iodide

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

Abstract

The solid-state structures of two quaternary trytpammonium salts, namely, N,N-dimethyl-N-n-propyl-tryptammonium (DMPT) iodide [systematic name: 2-(1H-indol-3-yl)-N,N-dimethyl-N-propyl-aza-nium iodide], C15H23N2 +·I-, and N-allyl-N,N-di-methyl-tryptammonium (DMALT) iodide, [systematic name: 2-(1H-indol-3-yl)-N,N-dimethyl-N-(prop-2-en-1-yl)aza-nium iodide], C15H21N2 +·I-, are reported. Both salts possess a tri-alkyl-tryptammonium cation and an iodide anion in the asymmetric unit, which are joined together through N-H⋯I inter-actions. The DMALT structure was refined as an inversion twin, and the allyl group is disordered over two orientations with a 0.70 (4):0.30 (4) ratio.

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

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Figures

Figure 1
Figure 1
The mol­ecular structure of DMPT iodide (left) and DMALT iodide (right), showing the atomic labelling. Displacement ellipsoids are drawn at the 50% probability level. Dashed bonds indicate a disordered component in the structure. Hydrogen bonds are shown as dashed lines.
Figure 2
Figure 2
The crystal packing of DMPT iodide (left), viewed along the a axis, and the crystal packing of DMALT iodide (right), viewed along the a axis. The hydrogen bonds (Tables 1 ▸ and 2 ▸) are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity. Only one component of the allyl disorder is shown in the DMALT structure.
See this image and copyright information in PMC

References

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    1. Chadeayne, A. R., Pham, D. N. K., Reid, B. G., Golen, J. A. & Manke, D. R. (2020). ACS Omega, https://doi. org/10.1021/acsomega.0c02208

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