Synthesis and structure of 4-hy­droxy-N-iso­propyl­tryptamine (4-HO-NiPT) and its precursors

ABSTRACT: The synthesis of the norpsilocin derivative, 4-hy­droxy-N-iso­propyl­tryptamine, is presented, as well as its crystal structure and the structures of its three synthetic precursors. The title compound, 4-hy­droxy-N-iso­propyl­tryptamine (4) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]­eth­yl}-1H-indol-4-ol), C13H18N2O, was synthesized in three steps from 4-benzyl­oxyindole (1) (systematic name: 4-phen­oxy-1H-indole), C15H13NO. (1) was treated with oxalyl chloride and iso­propyl­amine to produce N-isopropyl-4-benz­yloxy-3-indole­glyoxyl­amide (2) {systematic name: 2-[4-(benz­yloxy)-1H-indol-3-yl]-2-oxo-N-(propan-2-yl)acet­amide}, C20H20N2O3. (2) was reduced to generate 4-benz­yloxy-N-iso­propyl­tryptamine (3) or 4-HO-NiPT, which was characterized as its chloride salt 4-benz­ylox

SUBMITTER: Laban U 

PROVIDER: S-EPMC10088304 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature