Simultaneous Production of Psilocybin and a Cocktail of β‐Carboline Monoamine Oxidase Inhibitors in “Magic” Mushrooms
Felix Blei, Sebastian Dörner, Janis Fricke, Florian Baldeweg, Felix Trottmann, Anna J. Komor, Florian Meyer, Christian Hertweck, Dirk Hoffmeister
Chemistry - A European Journal November 14, 2019 DOI: 10.1002/chem.201904363 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Qualitative study Peer reviewed |
|---|---|
| Population | Four Psilocybe species |
| Topics | Psilocybin |
| Keywords | Harmine Monoamine oxidase Alkaloid Natural product Monoamine neurotransmitter Biochemistry Tryptophan Stereochemistry |
| Citations | 80 |
| Key findings | Psilocybe mushrooms produce β-carbolines, including harmane and harmine, which are potent monoamine oxidase inhibitors that interfere with psilocybin degradation. |
Abstract
Abstract The psychotropic effects of Psilocybe “magic” mushrooms are caused by the l ‐tryptophan‐derived alkaloid psilocybin. Despite their significance, the secondary metabolome of these fungi is poorly understood in general. Our analysis of four Psilocybe species identified harmane, harmine, and a range of other l ‐tryptophan‐derived β‐carbolines as their natural products, which was confirmed by 1D and 2D NMR spectroscopy. Stable‐isotope labeling with 13 C 11 ‐ l ‐tryptophan verified the β‐carbolines as biosynthetic products of these fungi. In addition, MALDI‐MS imaging showed that β‐carbolines accumulate toward the hyphal apices. As potent inhibitors of monoamine oxidases, β‐carbolines are neuroactive compounds and interfere with psilocybin degradation. Therefore, our findings represent an unprecedented scenario of natural product pathways that diverge from the same building block and produce dissimilar compounds, yet contribute directly or indirectly to the same pharmacological effects.
Comparable studies
Other qualitative studies on psilocybin, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Patients’ Accounts of Increased “Connectedness” and “Acceptance” After Psilocybin for Treatment-Resistant Depression Patients with treatment-resistant depression enrolled in an open-label trial of psilocybin | 2017 | Qualitative study | n = 20 |
| Patient Experiences of Psilocybin-Assisted Psychotherapy: An Interpretative Phenomenological Analysis Adults aged 22 to 69 with clinically elevated anxiety associated with a cancer diagnosis | 2017 | Qualitative study | n = 13 |
| Psychedelic therapy for smoking cessation: Qualitative analysis of participant accounts Participants who completed a psilocybin-facilitated smoking cessation pilot study | 2018 | Qualitative follow-up study using semi-structured interviews and thematic analysis | n = 12 |
| Response of cluster headache to psilocybin and LSD Cluster headache patients who used psilocybin or LSD | 2006 | Qualitative study | n = 53 |
| Cancer at the Dinner Table: Experiences of Psilocybin-Assisted Psychotherapy for the Treatment of Cancer-Related Distress Adult participants with clinically elevated anxiety associated with a cancer diagnosis | 2017 | Qualitative study using interpretative phenomenological analysis | n = 13 |
Citations in the library
Cited by 60
- The Therapeutic Potential of Psilocybin Molecules May 15, 2021
- Diversity, biology, and history of psilocybin-containing fungi: Suggestions for research and technological development. Fungal biology April 1, 2022
- 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 Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin Journal of Natural Products February 20, 2020
- Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis Drug Testing and Analysis October 29, 2020
and 55 more in the library
Cites 14
- The pharmacology of psilocybin Addiction Biology October 1, 2002
- Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose?effect study Psychopharmacology March 1, 2004
- Monoamine oxidase inhibitors in South American hallucinogenic plants: Tryptamine and β-carboline constituents of Ayahuasca Journal of Ethnopharmacology April 1, 1984
- Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen Helvetica Chimica Acta 1959
- Enzymatic Synthesis of Psilocybin Angewandte Chemie International Edition August 1, 2017
and 9 more in the library