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

• 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
• Format: Article
• Language: English
• Subjects: Research Communications
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989021000116

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.