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-N-eth-yl-N-methyl-tryptammonium (4-AcO-MET) hydro-fumarate {sys-tematic name: [2-(4-acet-yloxy-1H-indol-3-yl)eth-yl](meth-yl)ethyl-aza-nium 3-carb-oxy-prop-2-enoate}, C15H21N2O2 +·C4H3O4 -, 4-acet-oxy-N-allyl-N-methyl-tryptammonium (4-AcO-MALT) hydro-fumarate {systematic name: [2-(4-acet-yl-oxy-1H-indol-3-yl)eth-yl](meth-yl)prop-2-enyl-aza-nium 3-carb-oxy-prop-2-eno-ate}, C16H21N2O2 +·C4H3O4 -, and 4-acet-oxy-N,N-di-allyl-tryptammonium (4-AcO-DALT) fumarate-fumaric acid (1/1) (systematic name: bis-{[2-(4-acet-yloxy-1H-indol-3-yl)eth-yl]diprop-2-enyl-aza-nium} but-2-enedioate-(E)-butenedioic acid (1/1)), 2C18H23N2O2 +·C4H2O4 2-·C4H4O4, 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. © Pham et al. 2021.