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Bis(4-acetoxy-N-ethyl-N-n-propyltryptammonium) fumarate–fumaric acid (1/1)

Summary

Researchers determined the precise chemical structure of a synthetic compound related to psilocybin (the active ingredient in psychedelic mushrooms) using X-ray crystallography. The compound, 4-AcO-EPT, is designed to be converted in the body to a psychoactive substance with potential therapeutic benefits for depression and anxiety. The study resolved conflicting reports about the compound’s exact composition and molecular arrangement, showing it exists as a specific combination of three molecular components. This work demonstrates why chemists need to study actual crystal structures rather than relying solely on chemical calculations.

Background

Psilocybin and its analogues have shown therapeutic promise in treating various psychiatric disorders. Psilacetin (4-acetoxy-N,N-dimethyltryptamine) is a prodrug that hydrolyzes more efficiently than psilocybin to produce psilocin. 4-Acetoxy-N-ethyl-N-n-propyltryptamine (4-AcO-EPT) is a synthetic psychedelic prodrug analog with potentially improved pharmacological properties.

Objective

To determine the exact solid-state crystal structure of 4-AcO-EPT and clarify previous conflicting reports about its composition as either a fumarate, hydrofumarate, or fumarate-fumaric acid adduct. Single-crystal X-ray diffraction was employed to establish the definitive molecular composition and crystal packing arrangement.

Results

The asymmetric unit contains one 4-acetoxy-N-ethyl-N-n-propyltryptammonium cation, one half of a fumarate dianion, and one half of a fumaric acid molecule. The compound crystallizes in the triclinic space group P1 with Z=2. The structure reveals infinite one-dimensional chains propagating along [001] linked through N-H···O and O-H···O hydrogen bonds.

Conclusion

The compound is neither the simple fumarate nor hydrofumarate but rather a fumarate-fumaric acid adduct with a 1:1:1 molar ratio of tryptamine to fumaric acid equivalents. This work highlights the importance of crystallographic studies for determining the exact composition of crystalline tryptamine solids, correcting prior NMR-based assignments.
  • Published in:IUCrdata,
  • Study Type:Structural Chemistry Study,
  • Source: 10.1107/S2414314623007794; PMID: 37818476
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