Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin
Alexander M. Sherwood, Adam L. Halberstadt, Adam K. Klein, John D. Mccorvy, Kristi W. Kaylo, Robert B. Kargbo, Poncho Meisenheimer
Journal of Natural Products February 20, 2020 DOI: 10.1021/acs.jnatprod.9b01061 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Mice |
| Interventions | baeocystin norpsilocin |
| Topics | Psilocybin |
| Keywords | Tryptamines Hallucinogen Metabolite Pharmacology Agonist Harmine In vivo Biological activity In vitro Stereochemistry Biochemistry Receptor Biotechnology Alkaloids |
| Citations | 79 |
| Key findings | Baeocystin alone did not show psychedelic activity in the mouse head twitch response assay, whereas its metabolite norpsilocin is a potent 5-HT2A receptor agonist. |
Abstract
A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or lack thereof, of the natural products. In animal models, psychedelic activity by baeocystin alone was not evident using the mouse head twitch response assay, despite its putative dephosphorylated metabolite, norpsilocin, possessing potent agonist activity at the 5-HT2A receptor.
Comparable studies
Other preclinical and animal studies on psilocybin, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Psilocybin induces rapid and persistent growth of dendritic spines in frontal cortex in vivo Mice | 2021 | Observational cohort | |
| Harnessing psilocybin: antidepressant-like behavioral and synaptic actions of psilocybin are independent of 5-HT2R activation in mice Mice | 2021 | Experimental study | |
| Psychedelics reopen the social reward learning critical period Mice | 2023 | Experimental study in mice | |
| Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species. C57BL/6J mice | 2020 | Experimental study with dose-response experiments | |
| Effects of psilocybin on hippocampal neurogenesis and extinction of trace fear conditioning Mice | 2013 | Experimental study |
Citations in the library
Cited by 64
- Psilocybin induces rapid and persistent growth of dendritic spines in frontal cortex in vivo Neuron July 5, 2021
- The Therapeutic Potential of Psilocybin Molecules May 15, 2021
- Microdosing with psilocybin mushrooms: a double-blind placebo-controlled study Translational Psychiatry August 2, 2022
- 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
and 59 more in the library
Cites 17
- Enzymatic Synthesis of Psilocybin Angewandte Chemie International Edition August 1, 2017
- Pharmahuasca: Human Pharmacology of Oral DMT Plus Harmine Journal of Psychoactive Drugs April 1, 1999
- Acute Biphasic Effects of Ayahuasca PLoS One September 30, 2015
- Concise Large-Scale Synthesis of Psilocin and Psilocybin, Principal Hallucinogenic Constituents of “Magic Mushroom” Journal of Natural Products May 30, 2003
- Simultaneous Production of Psilocybin and a Cocktail of β‐Carboline Monoamine Oxidase Inhibitors in “Magic” Mushrooms Chemistry - A European Journal November 14, 2019
and 12 more in the library