Conformational Landscape and Properties of Psilocybin: A Computational Approach
Poonam Bhadoria, V. Ramanathan
ChemistrySelect October 4, 2022 DOI: 10.1002/slct.202203026 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Computational chemistry study Peer reviewed |
|---|---|
| Topics | Psilocybin |
| Keywords | Ethylamine Conformational isomerism Molecule Population Computational chemistry Stereochemistry Crystallography Hallucinogen |
| Citations | 5 |
| Key points | Psilocybin has two stable conformers with similar structural and spectroscopic properties, both matching the known crystal structure. |
Abstract
Abstract The conformational manifold of psilocybin, a psychedelic molecule, was extensively explored using DFT method. Two most stable conformers were identified and the second most stable conformer was found to be 2.08 kcal/mol higher than the global minimum. The barrier of rotation between the two conformers was found to be 14.63 kcal/mol. The structural and spectroscopic parameters of both these conformers were similar. AIM (Atoms in molecule) calculation revealed very strong intramolecular H‐bond interactions in both the conformers. The structural parameters of these two conformers significantly matched with the earlier reported crystal structure of psilocybin. Further properties of these conformers were investigated using FMO (Frontier molecular orbital), AIM (Atoms in molecule), ESP (Electrostatic potential) calculations. UV (Ultraviolet)‐visible, IR (Infrared) and 1 H‐NMR (Proton nuclear magnetic resonance) spectra were also computed. All the predicted results matched exceedingly well with the earlier reported literature.
Citations in the library
Cites 10
- Psilocybin produces substantial and sustained decreases in depression and anxiety in patients with life-threatening cancer: A randomized double-blind trial Journal of Psychopharmacology November 30, 2016
- Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance Psychopharmacology July 7, 2006
- Neural correlates of the psychedelic state as determined by fMRI studies with psilocybin Proceedings of the National Academy of Sciences January 23, 2012
- Psilocybin-assisted treatment for alcohol dependence: A proof-of-concept study Journal of Psychopharmacology January 13, 2015
- Psychedelics in Psychiatry: Neuroplastic, Immunomodulatory, and Neurotransmitter Mechanisms Pharmacological Reviews December 16, 2020
and 5 more in the library