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Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug

The solid-state structures of the salts of three psilacetin derivatives, namely, 4-acet-oxy- -eth-yl- -methyl-tryptammonium (4-AcO-MET) hydro-fumarate {sys-tematic name: [2-(4-acet-yloxy-1 -indol-3-yl)eth-yl](meth-yl)ethyl-aza-nium 3-carb-oxy-prop-2-enoate}, C H N O ·C H O , 4-acet-oxy- -allyl- -met...

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Published in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2021-02, Vol.77 (Pt 2), p.101-106
Main Authors: Pham, Duyen N K, Chadeayne, Andrew R, Golen, James A, Manke, David R
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Chadeayne, Andrew R
Golen, James A
Manke, David R
description The solid-state structures of the salts of three psilacetin derivatives, namely, 4-acet-oxy- -eth-yl- -methyl-tryptammonium (4-AcO-MET) hydro-fumarate {sys-tematic name: [2-(4-acet-yloxy-1 -indol-3-yl)eth-yl](meth-yl)ethyl-aza-nium 3-carb-oxy-prop-2-enoate}, C H N O ·C H O , 4-acet-oxy- -allyl- -methyl-tryptammonium (4-AcO-MALT) hydro-fumarate {systematic name: [2-(4-acet-yl-oxy-1 -indol-3-yl)eth-yl](meth-yl)prop-2-enyl-aza-nium 3-carb-oxy-prop-2-eno-ate}, C H N O ·C H O , and 4-acet-oxy- , -di-allyl-tryptammonium (4-AcO-DALT) fumarate-fumaric acid (1/1) (systematic name: bis-{[2-(4-acet-yloxy-1 -indol-3-yl)eth-yl]diprop-2-enyl-aza-nium} but-2-enedioate-( )-butenedioic acid (1/1)), 2C H N O ·C H O ·C H O , are reported. All three salts possess a protonated tryptammonium cation. The 4-AcO-MET and 4-AcO-MALT compounds are charge-balanced by 3-carb-oxy-acrylate (hydro-fumarate) anions. The 4-AcO-DALT complex crystallizes as a two-to-one tryptammonium-to-fumarate salt, which co-crystallizes with a fumaric acid mol-ecule. Each structure is consolidated by N-H⋯O and O-H⋯O hydrogen bonds.
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All three salts possess a protonated tryptammonium cation. The 4-AcO-MET and 4-AcO-MALT compounds are charge-balanced by 3-carb-oxy-acrylate (hydro-fumarate) anions. The 4-AcO-DALT complex crystallizes as a two-to-one tryptammonium-to-fumarate salt, which co-crystallizes with a fumaric acid mol-ecule. Each structure is consolidated by N-H⋯O and O-H⋯O hydrogen bonds.</description><identifier>ISSN: 2056-9890</identifier><identifier>EISSN: 2056-9890</identifier><identifier>DOI: 10.1107/S2056989021000116</identifier><identifier>PMID: 33614134</identifier><language>eng</language><publisher>England: International Union of Crystallography</publisher><subject>Research Communications</subject><ispartof>Acta crystallographica. 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Section E, Crystallographic communications</title><addtitle>Acta Crystallogr E Crystallogr Commun</addtitle><description>The solid-state structures of the salts of three psilacetin derivatives, namely, 4-acet-oxy- -eth-yl- -methyl-tryptammonium (4-AcO-MET) hydro-fumarate {sys-tematic name: [2-(4-acet-yloxy-1 -indol-3-yl)eth-yl](meth-yl)ethyl-aza-nium 3-carb-oxy-prop-2-enoate}, C H N O ·C H O , 4-acet-oxy- -allyl- -methyl-tryptammonium (4-AcO-MALT) hydro-fumarate {systematic name: [2-(4-acet-yl-oxy-1 -indol-3-yl)eth-yl](meth-yl)prop-2-enyl-aza-nium 3-carb-oxy-prop-2-eno-ate}, C H N O ·C H O , and 4-acet-oxy- , -di-allyl-tryptammonium (4-AcO-DALT) fumarate-fumaric acid (1/1) (systematic name: bis-{[2-(4-acet-yloxy-1 -indol-3-yl)eth-yl]diprop-2-enyl-aza-nium} but-2-enedioate-( )-butenedioic acid (1/1)), 2C H N O ·C H O ·C H O , are reported. All three salts possess a protonated tryptammonium cation. The 4-AcO-MET and 4-AcO-MALT compounds are charge-balanced by 3-carb-oxy-acrylate (hydro-fumarate) anions. The 4-AcO-DALT complex crystallizes as a two-to-one tryptammonium-to-fumarate salt, which co-crystallizes with a fumaric acid mol-ecule. 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Section E, Crystallographic communications</jtitle><addtitle>Acta Crystallogr E Crystallogr Commun</addtitle><date>2021-02-01</date><risdate>2021</risdate><volume>77</volume><issue>Pt 2</issue><spage>101</spage><epage>106</epage><pages>101-106</pages><issn>2056-9890</issn><eissn>2056-9890</eissn><abstract>The solid-state structures of the salts of three psilacetin derivatives, namely, 4-acet-oxy- -eth-yl- -methyl-tryptammonium (4-AcO-MET) hydro-fumarate {sys-tematic name: [2-(4-acet-yloxy-1 -indol-3-yl)eth-yl](meth-yl)ethyl-aza-nium 3-carb-oxy-prop-2-enoate}, C H N O ·C H O , 4-acet-oxy- -allyl- -methyl-tryptammonium (4-AcO-MALT) hydro-fumarate {systematic name: [2-(4-acet-yl-oxy-1 -indol-3-yl)eth-yl](meth-yl)prop-2-enyl-aza-nium 3-carb-oxy-prop-2-eno-ate}, C H N O ·C H O , and 4-acet-oxy- , -di-allyl-tryptammonium (4-AcO-DALT) fumarate-fumaric acid (1/1) (systematic name: bis-{[2-(4-acet-yloxy-1 -indol-3-yl)eth-yl]diprop-2-enyl-aza-nium} but-2-enedioate-( )-butenedioic acid (1/1)), 2C H N O ·C H O ·C H O , are reported. All three salts possess a protonated tryptammonium cation. The 4-AcO-MET and 4-AcO-MALT compounds are charge-balanced by 3-carb-oxy-acrylate (hydro-fumarate) anions. The 4-AcO-DALT complex crystallizes as a two-to-one tryptammonium-to-fumarate salt, which co-crystallizes with a fumaric acid mol-ecule. Each structure is consolidated by N-H⋯O and O-H⋯O hydrogen bonds.</abstract><cop>England</cop><pub>International Union of Crystallography</pub><pmid>33614134</pmid><doi>10.1107/S2056989021000116</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-8599-1565</orcidid><oa>free_for_read</oa></addata></record>
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title Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug
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