Simultaneous Production of Psilocybin and a Cocktail of β‐Carboline Monoamine Oxidase Inhibitors in “Magic” Mushrooms

Blei, Felix; Dörner, Sebastian; Fricke, Janis; Baldeweg, Florian; Trottmann, Felix; Komor, Anna J.; Meyer, Florian; Hertweck, Christian; Hoffmeister, Dirk

doi:10.1002/chem.201904363

Cited by 47 publications

(47 citation statements)

References 36 publications

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“…Despite decades of analytical work on the genus Psilocybe and although known from other sources, [43] several β-carbolines, including harmane, norharmane, and harmine (Scheme 1), were discovered as natural products of various Psilocybe species only very recently. [44] The 1,2,3,4-tetrahydrocarboline core represents the primary cyclization product formed via a Schiff base intermediate, when tryptamine is condensed by Pictet-Spengler-type chemistry with aldehydes or an α-keto acid. Therefore, the β-carbolines contrast psilocybin biosynthesis (as well as that of N,N-dimethyl-l-tryptophan, presented in the following section).…”

Section: Another L-tryptophan-fed Pathway In Psilocybementioning

confidence: 99%

Taking Different Roads: l‐Tryptophan as the Origin of Psilocybe Natural Products

et al. 2020

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Psychotropic fungi of the genus Psilocybe, colloquially referred to as „magic mushrooms”, are best known for their l‐tryptophan‐derived major natural product, psilocybin. Yet, recent research has revealed a more diverse secondary metabolism that originates from this amino acid. In this minireview, the focus is laid on l‐tryptophan and the various Psilocybe natural products and their metabolic routes are highlighted. Psilocybin and its congeners, the heterogeneous blue‐colored psilocyl oligomers, alongside β‐carbolines and N,N‐dimethyl‐l‐tryptophan, are presented as well as current knowledge on their biosynthesis is provided. The multidisciplinary character of natural product research is demonstrated, and pharmacological, medicinal, ecological, biochemical, and evolutionary aspects are included.

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Section: Another L-tryptophan-fed Pathway In Psilocybementioning

confidence: 99%

Taking Different Roads: l‐Tryptophan as the Origin of Psilocybe Natural Products

et al. 2020

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“…Psychoactive mushrooms have been used as entheogens during transcendental ceremonies by Mexican inhabitants, mainly by shamans, for thousands of years. Mushrooms used for religious and spiritual rituals are called “magic mushrooms.” 1–3 There are many mushroom species that contain high levels of psychotropic tryptamines, including the genera Pluteus , Panaeolus , Inocybe , Gymnopilus , Galerina , Pholiotina , and especially Psilocybe 4–7 . In the 1950s, these magic mushrooms were introduced to Europe thanks to Gordon Wasson, who brought them from Mexico from the shaman Maria Sabina of the Mazatec tribe 8,9 .…”

Section: Introductionmentioning

confidence: 99%

Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis

Gotvaldová

Hájková

Borovička

et al. 2020

Drug Testing and Analysis

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Psilocybin, psilocin, baeocystin, norbaeocystin, and aeruginascin are tryptamines structurally similar to the neurotransmitter serotonin. Psilocybin and its pharmacologically active metabolite psilocin in particular are known for their psychoactive effects. These substances typically occur in most species of the genus Psilocybe (Fungi, Strophariaceae). Even the sclerotia of some of these fungi known as “magic truffles” are of growing interest in microdosing due to them improving cognitive function studies. In addition to microdosing studies, psilocybin has also been applied in clinical studies, but only its pure form has been administrated so far. Moreover, the determination of tryptamine alkaloids is used in forensic analysis. In this study, freshly cultivated fruit bodies of Psilocybe cubensis were used for monitoring stability (including storage and processing conditions of fruiting bodies). Furthermore, mycelium and the individual parts of the fruiting bodies (caps, stipes, and basidiospores) were also examined. The concentration of tryptamines in final extracts was analyzed using ultra‐high‐performance liquid chromatography coupled with mass spectrometry. No tryptamines were detected in the basidiospores, and only psilocin was present at 0.47 wt.% in the mycelium. The stipes contained approximately half the amount of tryptamine alkaloids (0.52 wt.%) than the caps (1.03 wt.%); however, these results were not statistically significant, as the concentration of tryptamines in individual fruiting bodies is highly variable. The storage conditions showed that the highest degradation of tryptamines was seen in fresh mushrooms stored at −80°C, and the lowest decay was seen in dried biomass stored in the dark at room temperature.

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“…In a report earlier this year, -carboline MAO inhibitors were identified in species of 'magic mushrooms', where the primary psychedelic, psilocin, can be similarly degraded by MAO. This is the first instance of a synchronous biosynthesis of an active ingredient and the inhibitor of its degradation in a natural psychedelic species (Blei et al, 2020). Psilocin (4-hydroxy-N,N-dimethyltryptamine) is orally active in the absence of MAO inhibitors, indicating that the 4-hydroxy substitution makes the compound more resistant to deamination by MAO (Sherwood et al, 2020).…”

Section: Chemical Contextmentioning

confidence: 90%

DMT analogues: N-ethyl-N-propyltryptamine and N-allyl-N-methytryptamine as their hydrofumarate salts

Chadeayne¹,

Pham²,

Golen³

et al. 2020

Acta Cryst E

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The solid-state structures of the hydrofumarate salts of two N,N-dialkyltryptamines, namely N-ethyl-N-propyltryptammonium (EPT) hydrofumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)propylazanium 3-carboxyprop-2-enoate}, C15H23N2 +·C4H3O4 −, and N-allyl-N-methyltryptammonium (MALT) hydrofumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)(prop-2-en-1-yl)azanium 3-carboxyprop-2-enoate}, C14H19N2 +·C4H3O4 −, are reported. Both compounds possess a protonated tryptammonium cation, and a hydrofumarate anion in the asymmetric unit. The ethyl group of the EPT cation is modeled as a two-component disorder with 50% occupancy for each component. In the extended structure, N—H...O and O—H...O hydrogen bonds generate infinite two-dimensional networks parallel to the (001) plane for both compounds.

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Simultaneous Production of Psilocybin and a Cocktail of β‐Carboline Monoamine Oxidase Inhibitors in “Magic” Mushrooms

Cited by 47 publications

References 36 publications

Taking Different Roads: l‐Tryptophan as the Origin of Psilocybe Natural Products

Taking Different Roads: l‐Tryptophan as the Origin of Psilocybe Natural Products

Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis

DMT analogues: N-ethyl-N-propyltryptamine and N-allyl-N-methytryptamine as their hydrofumarate salts

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