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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Syntheses and structures of two norpsilocin derivatives: N-ethyl-4-hy-droxy-tryptamine (4-HO-NET) and

Marilyn Naeem1, Andrew R Chadeayne2, James A Golen1

  • 1University of Massachusetts Dartmouth 285 Old Westport Road North Dartmouth MA 02747 USA.

Acta Crystallographica. Section E, Crystallographic Communications
|September 8, 2026
PubMed

Keywords:
crystal structurehydrogen bondsindolestryptamines

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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
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Basicity of Heterocyclic Aromatic Amines

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