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Norpsilocin: freebase and fumarate salt

Summary

Researchers determined the crystal structures of norpsilocin, a naturally occurring compound found in magic mushrooms that is chemically similar to psilocin. This work is important because norpsilocin appears to be as potent as psilocin at serotonin receptors and may contribute to the therapeutic effects of magic mushroom extracts. By obtaining pure crystalline forms and understanding the compound’s structure, scientists can better study its properties and potential medical applications for treating conditions like depression and anxiety.

Background

Norpsilocin (4-hydroxy-N-methyltryptamine) is a naturally occurring psychoactive tryptamine found in magic mushrooms that serves as the active metabolite of baeocystin. Despite growing evidence supporting psilocin/psilocybin’s potential for treating mood disorders, very little work has been done to investigate structurally similar compounds like norpsilocin due to their limited availability in pure form.

Objective

To report the first crystal structure of norpsilocin freebase and the synthesis and structure of its fumarate salt, providing important structural characterization needed for examining the structure-activity relationship of this psychedelic tryptamine.

Results

The freebase norpsilocin forms a two-dimensional hydrogen-bonded network parallel to the (100) plane with disorder in the ethylamine arm. The fumarate salt crystallizes as a 2:1 tryptammonium-to-fumarate salt forming a three-dimensional framework with π-π stacking interactions between indole rings. Both structures show extensive N-H···O and O-H···O hydrogen bonding patterns.

Conclusion

The crystal structures of norpsilocin freebase and fumarate salt are now characterized, providing fundamental structural information for understanding this psychedelic compound’s properties. These solid-state structures offer convenient and reliable chemical forms for studying, handling, and administering pure norpsilocin for further pharmacological investigation.
  • Published in:Acta Crystallographica Section E: Crystallographic Communications,
  • Study Type:Structural Characterization Study,
  • Source: 10.1107/S2056989020004077; PMID: 32280510
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