The crystal structure of baeocystin
Marilyn Naeem, Alexander M. Sherwood, Andrew R Chadeayne, James A. Golen, David R. Manke
Acta Crystallographica. Section E, Crystallographic Communications May 6, 2022 DOI: 10.1107/s2056989022004467 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Crystallographic study Peer reviewed |
|---|---|
| Keywords | Crystal structure Crystallography Alkaloids |
| Citations | 5 |
| Key points | Baeocystin crystallizes as a zwitterion with an intramolecular N—H...O hydrogen bond and forms a three-dimensional hydrogen-bonded network in the crystal. |
Abstract
The title compound, baeocystin or 4-phosphoryloxy- N -methyltryptamine {systematic name: 3-[2-(methylazaniumyl)ethyl]-1 H -indol-4-yl hydrogen phosphate}, C 11 H 15 N 2 O 4 P, has a single zwitterionic molecule in the asymmetric unit. The molecule has an intramolecular N—H...O hydrogen bond between the ammonium cation and the hydrophosphate anion. In the crystal, the molecules are linked by N—H...O and O—H...O hydrogen bonds into a three-dimensional network.
Citations in the library
Cited by 4
- Structure–Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice ACS Pharmacology & Translational Science November 2, 2022
- Synthesis and structure of 4-hydroxy-N-isopropyltryptamine (4-HO-NiPT) and its precursors Acta Crystallographica. Section E, Crystallographic Communications March 10, 2023
- Syntheses and structures of two norpsilocin derivatives: N-ethyl-4-hy-droxy-tryptamine (4-HO-NET) and 4-hy-droxy-N-propyl-tryptamine (4-HO-NPT). Acta Crystallographica. Section E, Crystallographic Communications September 1, 2026
- The methanol and ethanol solvates of 4-glutarato-N,N-diisopropyltryptamine Acta Crystallographica. Section E, Crystallographic Communications September 22, 2022
Cites 11
- Potential Therapeutic Effects of Psilocybin. Neurotherapeutics July 1, 2017
- Enzymatic Synthesis of Psilocybin Angewandte Chemie International Edition August 1, 2017
- The promises and perils of psychedelic pharmacology for psychiatry. Nature Reviews Drug Discovery June 1, 2022
- DARK Classics in Chemical Neuroscience: Psilocybin ACS Chemical Neuroscience June 29, 2018
- Psychedelic drugs—a new era in psychiatry? Dialogues in Clinical Neuroscience June 30, 2019
and 6 more in the library