Bis(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug

The title compound (systematic name: bis­{2-[4-(acet­yloxy)-1H-indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C(14)H(19)N(2)O(2) (+)·C(4)H(2)O(4) (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 ammo...

Descripción completa

Detalles Bibliográficos
Autores principales: Chadeayne, Andrew R., Golen, James A., Manke, David R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658936/
https://www.ncbi.nlm.nih.gov/pubmed/31391991
http://dx.doi.org/10.1107/S2056989019007370
_version_ 1783439038667030528
author Chadeayne, Andrew R.
Golen, James A.
Manke, David R.
author_facet Chadeayne, Andrew R.
Golen, James A.
Manke, David R.
author_sort Chadeayne, Andrew R.
collection PubMed
description The title compound (systematic name: bis­{2-[4-(acet­yloxy)-1H-indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C(14)H(19)N(2)O(2) (+)·C(4)H(2)O(4) (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].
format Online
Article
Text
id pubmed-6658936
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-66589362019-08-07 Bis(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug Chadeayne, Andrew R. Golen, James A. Manke, David R. Acta Crystallogr E Crystallogr Commun Research Communications The title compound (systematic name: bis­{2-[4-(acet­yloxy)-1H-indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C(14)H(19)N(2)O(2) (+)·C(4)H(2)O(4) (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]. International Union of Crystallography 2019-05-31 /pmc/articles/PMC6658936/ /pubmed/31391991 http://dx.doi.org/10.1107/S2056989019007370 Text en © Chadeayne et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Chadeayne, Andrew R.
Golen, James A.
Manke, David R.
Bis(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
title Bis(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
title_full Bis(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
title_fullStr Bis(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
title_full_unstemmed Bis(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
title_short Bis(4-acet­oxy-N,N-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
title_sort bis(4-acet­oxy-n,n-di­methyl­tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658936/
https://www.ncbi.nlm.nih.gov/pubmed/31391991
http://dx.doi.org/10.1107/S2056989019007370
work_keys_str_mv AT chadeayneandrewr bis4acetoxynndimethyltryptammoniumfumarateanewcrystallineformofpsilacetinanalternativetopsilocybinasapsilocinprodrug
AT golenjamesa bis4acetoxynndimethyltryptammoniumfumarateanewcrystallineformofpsilacetinanalternativetopsilocybinasapsilocinprodrug
AT mankedavidr bis4acetoxynndimethyltryptammoniumfumarateanewcrystallineformofpsilacetinanalternativetopsilocybinasapsilocinprodrug

Ejemplares similares