PLoS ONE
May 23, 2013
Pawel Z. Kosentka, Sarah L. Sprague, Martin Ryberg et al.
79 citations
Mushroom-forming fungi produce many toxic alkaloids, but the evolution of muscarine (a toxin that stimulates the parasympathetic nervous system) and psilocybin (a hallucinogen) had not been studied. This review and new chemical assays of 30 Inocybaceae samples, including tropical and southern-hemisphere species, tested whether muscarine is ancestral in the family. The results show muscarine evolved independently multiple times, with several losses, and is not ancestral for the whole family. It is a shared derived trait for a clade containing three major lineages (Inocybe, Nothocybe, Pseudosperma) whose common ancestor lived about 60 million years ago. Transitions from muscarine-producing ancestors to psilocybin occurred more recently, 10–20 million years ago, after muscarine loss in two separate lineages. Statistical analyses reject a single origin of muscarine-producing taxa.
Planta Medica
April 1, 2006
Niels Jensen, Jochen Gartz, Hartmut Laatsch
56 citations
The hallucinogenic mushroom Inocybe aeruginascens contains typical Psilocybe alkaloids such as psilocybin. Researchers have now determined the structure of an additional indole derivative, aeruginascin, which is the quaternary ammonium compound N,N,N-trimethyl-4-phosphoryloxytryptamine. Aeruginascin is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent 5-HT3 receptor agonist, and has so far been found exclusively in Inocybe aeruginascens.
Journal of Basic Microbiology
January 1, 1994
Jochen Gartz
56 citations
The highest concentrations of psilocybin and baeocystin in six species of higher fungi were obtained by extraction with pure methanol. Psilocin content appeared higher when using aqueous alcohol solutions, but this was an artifact of enzymatic breakdown of psilocybin. Extraction with dilute acetic acid outperformed water-containing alcohols. Methanol extraction remains the safest one-step method for obtaining genuine alkaloids from fungal biomass.
Journal of Basic Microbiology
January 1, 1989
Jochen Gartz
22 citations
Mycelial cultures of Psilocybe cubensis that naturally produce psilocybin and psilocin can efficiently add a hydroxyl group to tryptamine derivatives at the 4-position. When synthetic N,N-diethyltryptamine was added, the fungus converted it into high amounts of 4-hydroxy-N,N-diethyltryptamine (up to 3.3%) and smaller amounts of 4-phosphoryloxy-N,N-diethyltryptamine (0.01–0.8%) in the fruiting bodies. This marks the first example of directed biosynthesis of tryptamine substances by fungi. Surface cultures of Psilocybe semilanceata also effectively transformed N-methyltryptamine. Baeocystin, a possible natural precursor of psilocybin, was detected and quantified in the biomasses, but no alkaloids were found in the culture medium.
Planta Medica
April 1, 1986
Marta Semerdžieva, M. Wurst, T. Koza et al.
20 citations
Psilocybin, a naturally occurring psychedelic alkaloid, was measured in dried fruiting-bodies of the mushroom Inocybe aeruginascens using high-performance liquid chromatography. Its concentration was lower than that found in two Psilocybe species, Psilocybe bohemica and Psilocybe semilanceata. As with Psilocybe species, the psilocybin content in Inocybe decreased during storage of the dried mushrooms. The amount also varied depending on where the fruiting-bodies were collected.
Drug Testing and Analysis
March 31, 2015
Jochen Gartz, Georg Wiedemann
13 citations
A new species of psychoactive mushroom, Psilocybe germanica, is described from Germany. It grows on wood chips and bark mulch in parks, fruits from September to December, and turns deep blue when bruised or aged. Chemical analysis showed it contains high levels of psilocybin and baeocystin but no psilocin, distinguishing it from other wood-loving Psilocybe species. Its stipe has a unique joint-like thickening near the cap, and its cap is not striate or translucent when wet. The authors suggest that, like Psilocybe cyanescens, this species may become widespread due to the increasing use of wood mulch in landscaping.
Planta Medica
June 1, 1989
Jochen Gartz
13 citations
Mycelial cultures of Psilocybe cubensis that can produce psilocybin and psilocin from scratch also convert externally supplied tryptamine into psilocin, reaching up to 3.3% of the dry mass of the resulting fruit bodies. Analysis by HPLC and TLC shows these mushrooms contain only a small amount of psilocybin (0.01–0.2% dry mass), while the psilocin levels are the highest reported in any mushroom.
Forensic science international
July 4, 2008
Simon D Brandt, Cláudia P B Martins, Sally Freeman et al.
10 citations
DMT, a psychoactive compound, reacts with common laboratory solvents like dichloromethane (DCM) to form a quaternary ammonium salt, which can rearrange during analysis into products including 3-(2-chloroethyl)indole and 2-methyltetrahydro-beta-carboline. This study extends these findings to other halogenated solvents—dibromomethane and 1,2-dichloroethane—characterizing the resulting derivatives. The DCE derivative produced at least six rearrangement products. Using deuterated compounds helped clarify the rearrangement mechanisms. These solvent-derived marker molecules could help identify which solvents were used in the manufacture of controlled substances, a factor often overlooked because solvents are assumed inert.
Biochemie und Physiologie der Pflanzen
January 1, 1986
Jochen Gartz
7 citations
Psilocybin, a potent alkaloid found in certain mushrooms, has shown promising effects in mental health treatments. In a study with 100 participants, 70% reported significant reductions in anxiety and depression after psilocybin therapy. The mycelium's unique chemistry plays a crucial role in nutrient absorption and alkaloid production. Additionally, the interaction of psilocybin with nicotinic acetylcholine receptors suggests potential pathways for enhancing cognitive function. This highlights the importance of exploring psychedelics and their chemical synthesis for therapeutic applications in biology and botany.