The crystal structure of baeocystin
Marilyn Naeem, Alexander M. Sherwood, A.r. Chadeayne, James A. Golen, David R. Manke
Acta Crystallographica Section E Crystallographic Communications May 6, 2022 DOI: 10.1107/s2056989022004467 via OpenAlex
Summary
The crystal structure of baeocystin, a naturally occurring alkaloid related to psilocybin, was determined. The molecule exists as a zwitterion with an intramolecular hydrogen bond between its ammonium and phosphate groups. In the crystal, these molecules form a three-dimensional network through N—H...O and O—H...O hydrogen bonds.
Study at a glance
| Characteristics | Peer reviewed |
|---|---|
| Keywords | Chemistry Crystal structure Crystallography Alkaloids |
| Citations | 5 |
| Key finding | 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.