Bis(4-hydroxy-N,N-di-n-propyltryptammonium) fumarate tetrahydrate

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

doi:10.1107/s241431461901469x

Andrew R Chadeayne, David R Manke + Show 2 more

Open Access

https://doi.org/10.1107/s241431461901469x

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Journal: IUCrData	Publication Date: Nov 12, 2019
License type: CC BY 4.0

Affiliation: University of Massachusetts Dartmouth

Abstract

The title compound (systematic name: bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl]bis(propan-2-yl)azanium} but-2-enedioate tetrahydrate), 2C16H25N2O+·C4H2O4 2−·4H2O, has a singly protonated DPT cation, one half of a fumarate dianion (completed by a crystallographic centre of symmetry) and two water molecules of crystallization in the asymmetric unit. A series of N—H...O and O—H...O hydrogen bonds form a three-dimensional network in the solid state.

Highlights

The title compound (systematic name: bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl]bis(propan-2-yl)azanium} but-2-enedioate tetrahydrate), 2C16H25N2O+ÁC4H2O42ÀÁ4H2O, has a singly protonated DPT cation, one half of a fumarate dianion and two water molecules of crystallization in the asymmetric unit
A series of N—HÁ Á ÁO and O—HÁ Á ÁO hydrogen bonds form a three-dimensional network in the solid state
Psilocin is the metabolite of psilocybin and its synthetic analogue psilacetin, and is a serotonin-2a agonist which results in its mood-altering effects

Summary

Structure description

4-Hydroxy-N,N-di-n-propyltryptamine, or 4-HO-DPT, is a derivative of psilocin, which is the primary active psychedelic in ‘magic’ mushrooms. Psilocin is the metabolite of psilocybin and its synthetic analogue psilacetin, and is a serotonin-2a agonist which results in its mood-altering effects Tryptamines, both naturally occurring [Psilocybin (Weber & Petcher, 1974), Psilocin (Petcher & Weber, 1974), and DMT (Falkenberg, 1972)] and their synthetic derivatives [Psilacetin (Chadeayne et al 2019a,b), MPT (Chadeayne et al 2019c), MiPT, and 4-HO-MiPT (Chadeayne, Pham et al 2019)] have garnered a great deal of interest because of their potential to treat depression and posttraumatic stress disorder (PTSD) (Carhart-Harris & Goodwin, 2017). The solid-state structures of bioactive tryptamine molecules are significant because they define each molecule’s physical identity, thereby providing the foundation for all downstream research. Such fundamental structural characterization is essential for understanding each molecule’s biological and clinical properties via structure-activity relationships.

DÁ Á ÁA

Synthesis and crystallization

Data collection Diffractometer Absorption correction

Crystal data

Data collection

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