Norpsilocin: freebase and fumarate salt

Area of Science:

• Crystallography
• Solid-state chemistry
• Psychoactive compounds

Background:

• Norpsilocin (4-hydroxy-N-methyl-tryptamine) is a naturally occurring psychoactive tryptamine.
• Understanding the solid-state structures of psychoactive compounds is crucial for their chemical and pharmacological characterization.

Purpose of the Study:

• To determine and report the solid-state crystal structures of norpsilocin freebase and its fumarate salt.
• To elucidate the intermolecular interactions and structural features in the crystalline forms.

Main Methods:

• Single-crystal X-ray diffraction was used to analyze the crystal structures.
• Structural analysis included identifying hydrogen bonding networks and molecular disorder.

Main Results:

• The crystal structure of norpsilocin freebase features a 2D network formed by N-H⋯O and O-H⋯O hydrogen bonds.
• The ethyl-amine arm of norpsilocin freebase exhibits two-component disorder.
• The fumarate salt forms a 3D framework via hydrogen bonding and displays π-π stacking between indole rings.

Conclusions:

• The study provides detailed structural insights into norpsilocin and its salt.
• The observed structural features, including hydrogen bonding and disorder, are important for understanding the compound's properties.