Journal of Natural Products
May 30, 2003
Osamu Shirota, Wataru Hakamata, Yukihiro Goda
90 citations
Psilocin and psilocybin, the main hallucinogenic compounds in magic mushrooms, can be synthesized on a large scale without the need for chromatographic purification. The key step in producing psilocybin involves isolating a dibenzyl-protected intermediate as a zwitterionic derivative, which was fully characterized using two-dimensional NMR analyses.
Journal of Natural Products
February 20, 2020
Alexander M. Sherwood, Adam L. Halberstadt, Adam K. Klein et al.
79 citations
A new synthetic method allows access to tryptamine natural products found in psilocybin-producing mushrooms. Laboratory and animal experiments tested whether these compounds are psychoactive. In mice, the natural product baeocystin did not produce a head twitch response, a behavioral marker of psychedelic activity, even though its predicted breakdown product, norpsilocin, strongly activates the 5-HT2A receptor, which is associated with psychedelic effects. This suggests that baeocystin itself may not be psychedelic, despite its metabolite's activity.
Journal of Natural Products
September 20, 2017
Claudius Lenz, Jonas Wick, Dirk Hoffmeister
62 citations
A previously unreported natural compound, ω-N-methyl-4-hydroxytryptamine (norpsilocin), was identified in the fruiting bodies of the hallucinogenic mushroom Psilocybe cubensis. Its structure was determined using NMR spectroscopy and high-resolution mass spectrometry. Norpsilocin is likely the actual psychoactive agent released from its phosphate ester derivative, the known natural product baeocystin. The authors also developed a simple extraction method that avoids dephosphorylation, thereby preserving the natural metabolic profile of Psilocybe mushrooms for analysis.
Journal of Natural Products
May 1, 1981
Yutaka Koike, Kohko Wada, Genjiro Kusano et al.
45 citations
Psilocybin was isolated from the mushroom Psilocybe argentipes and its presence was determined in specimens of several mushroom species. The work details the chemical isolation and analytical methods used to identify and quantify the alkaloid in these fungi.
Journal of Natural Products
July 1, 1987
E. Ohenoja, J. Jokiranta, T. Mäkinen et al.
21 citations
Psilocybin and psilocin, the psychoactive compounds known from hallucinogenic mushrooms, were detected in several species of Finnish fungi. The study identified these alkaloids in specimens collected from various locations in Finland, confirming their presence in the region's fungal flora. The chemical analysis provided evidence for the occurrence of these substances, contributing to the understanding of their distribution in nature.
Journal of Natural Products
March 5, 2021
Janis Fricke, Alexander M. Sherwood, Adam L. Halberstadt et al.
18 citations
A novel analogue of psilocybin, 5-methylpsilocybin, was produced through a hybrid chemoenzymatic synthesis, combining chemical synthesis of 5-methylpsilocin with enzymatic phosphorylation using a purified kinase from Psilocybe cubensis. The product was isolated with high purity via solvent-antisolvent precipitation. In a mouse head-twitch response assay, 5-methylpsilocybin showed psychedelic-like activity more potent than dimethyltryptamine but less potent than psilocybin.
Journal of Natural Products
July 1, 1986
W.-w. Ma, Xiaomo Jiang, R. Graham Cooks et al.
10 citations
Mescaline and related alkaloids were identified in eight additional cactus species using thin-layer chromatography (TLC) and tandem mass spectrometry (MS/MS). The work extends the known distribution of these compounds across the Cactaceae family.
Journal of Natural Products
March 1, 1982
Sunibhond Pummangura, Jerry L. Mclaughlin, R. C. Schifferdecker
10 citations
Grafting Trichocereus cacti does not cause mescaline to move from a mescaline-producing scion into a non-producing rootstock. The study tested for alkaloid translocation by grafting mescaline-containing Trichocereus tops onto non-alkaloid-producing rootstocks and analyzing the rootstock tissue. No mescaline was detected in the rootstocks, indicating that mescaline does not translocate across the graft union under the conditions tested. The finding suggests that mescaline remains localized in the tissues where it is synthesized.