Diversity, biology, and history of psilocybin-containing fungi: Suggestions for research and technological development

Structure–Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice

“…4-Phosphoryloxy- N , N -dimethyltryptamine (psilocybin) is a naturally occurring tertiary amine found in diverse mushroom species throughout the world. − Psilocybin-containing mushrooms, sometimes colloquially called “magic mushrooms”, have been used for centuries as religious sacraments to facilitate spiritual or mystical-type subjective experiences. − Additionally, psilocybin-containing mushrooms are used in various recreational contexts, which can pose risks to public health. , Psychedelics like psilocybin, − its active metabolite 4-hydroxy- N , N -dimethyltryptamine (psilocin), − and some other related compounds are designated as controlled substances internationally. Legal restrictions on psychedelic compounds have significantly hindered research efforts aimed at understanding their complex pharmacology. ,, However, in recent times, there is renewed interest in the therapeutic potential of psychedelics, and psilocybin has been investigated as an adjunct to psychotherapy in the treatment of psychological distress in end stage cancer, depression, substance use disorders, chronic pain, and obsessive-compulsive disorders. ,− …”

“…Preclinical evaluation of baeocystin in the mouse head twitch response (HTR) assay, which predicts psychedelic subjective effects in humans, shows that the substance does not produce effects in vivo . Pharmacological evaluations of tryptamines other than psilocybin and psilocin are lacking, despite initiatives in the USA to legalize or decriminalize psilocybin-containing mushrooms, many of which contain the aforementioned psilocybin analogues. ,,− …”

“…Some psychoactive mushroom species contain other potentially bioactive compounds in addition to psilocybin, including various tryptamines, β-carbolines, and terpenes. ,, Underexplored tryptamines present in psilocybin-containing mushrooms include 4-phosphoryloxy- N -methyltryptamine (baeocystin), 4-phosphoryloxy- N , N , N -trimethyltryptamine (aeruginascin), 4-hydroxy- N -methyltryptamine (norpsilocin), and 4-phosphoryloxytryptamine (norbaeocystin) − (see Figure ). The precise amounts of these tryptamines relative to that of psilocybin vary across mushroom species, but the compounds are found in mushroom species commonly ingested by humans, such as Psilocybe cubensis .…”

Distribution of the gyromitrin mycotoxin in the lorchel family assessed by a pre-column-derivatization and ultra high-performance liquid chromatography method

“…BGCs can experience strong selective pressure due to their importance in ecological interactions that often results in a narrow taxonomic distribution as well as intraspecific variation in the ability to produce a given secondary metabolite (Rokas et al 2020;Yancey et al 2022). Horizontal gene transfer is also a powerful evolutionary force that has led to the broad and phylogenetically disjunct expression of mycotoxins such as amanitin, psilocybin, and epipolythiodioxopiperazines (Patron et al 2007;Rokas et al 2020;Luo et al 2022;Van Court et al 2022). Therefore, a disjointed distribution of gyromitrin is not unprecedented.…”

Therapeutic use of psilocybin: Practical considerations for dosing and administration

“…The interest in psilocybin as a therapeutic approach has grown exponentially in recent years. Primarily originating from fungal species within the genus Psilocybe , psilocybin is an indole alkaloid that is the main psychedelic ingredient in psychedelic mushrooms ( 1 ). Psilocybe mushroom species are pan-tropical, growing around the globe, including in the regions of the southeastern United States, Central and South America, South East Asia, and parts of Africa ( 2 , 3 ).…”