Summary

Top 10 papers analyzed

Based on the information provided in the summaries, psilocybin is not a phosphorylation of psilocin. Rather, psilocybin is synthesized through a chemical reaction that involves the condensation of 4-phosphoryloxy-N,N-dimethyltryptamine with L-serine or L-threonine. Psilocin, on the other hand, is a metabolite of psilocybin that is produced by the removal of the phosphoryl group from psilocybin by the enzyme alkaline phosphatase. The metabolic engineering of Saccharomyces cerevisiae for the de novo production of psilocybin and related tryptamine derivatives suggests that in vivo PcPsiK is catalyzing the conversion of psilocin back to psilocybin. Psilocybin has been synthesized through total chemical synthesis and modified synthesis from psilocin reported by Kargbo et al. In clinical studies with psilocybin, tablets containing 2 mg of psilocybin were distributed under the trade name Indocybin™ by Sandoz Pharmaceuticals in 1960. Overall, while psilocybin and psilocin are related compounds, psilocybin is not a phosphorylation of psilocin but rather a precursor that is metabolized into psilocin.

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Psilocybin: from ancient magic to modern medicine Scheme 1 Total chemical synthesis of psilocybin Scheme 2 Modified synthesis of psilocybin from psilocin reported by Kargbo et al. Clinical studies with psilocybin Following the identification and synthesis of psilocybin, in 1960 Sandoz Pharmaceuticals began distributing tablets containing 2 mg of psilocybin under the trade name Indocybin™.

Published By:

DE Nichols - The Journal of antibiotics, 2020 - nature.com

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70

The parameters of the ion source In summary, the yields of the analytes from the dried mushroom were as follows: drying gas temperature 340 C, drying gas powder in comparison with the unprocessed dried mushrooms were flow 10 Lmin−1, nebulizer 25 psig, sheath gas temperature as follows: 16% increase in psilocybin, 13% increase in psilocin, 74% 400 C, sheath gas flow 12 Lmin−1, and capillary voltage increase in baeocystin, and 40% increase in aeruginascin. According to the previous results from the homogenization effects, the dried mushrooms were analyzed as mushroom powder and fresh mushrooms in whole pieces for the highest possible yield.

Published By:

K Gotvaldová, K Hájková, J Borovička… - Drug testing and …, 2021 - Wiley Online Library

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25

Metabolic engineering of Saccharomyces cerevisiae for the de novo production of psilocybin and related tryptamine derivatives Under a Creative Commons license open access Highlights De novo production of psilocybin in S. cerevisiae. During fed-batch fermentation of the top psilocybin producing strain ST9482 a decrease in psilocin and corresponding increase in psilocybin titer was observed after 139h suggesting that in vivo PcPsiK is catalyzing the conversion of psilocin back to psilocybin.

Published By:

N Milne, P Thomsen, N Knudsen, P Rubaszka… - Metabolic …, 2020 - Elsevier

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58

LD50 values methanol extract I Pholiotina cyanopus 316.87 1.63 methanol extract II Psilocybe semilanceata 324.37 2.04 Psilocin 293.07 1.02 Toxins 2015, 7 1021 The comparison of the obtained LD50 values for synthetic psilocin and fungal extracts in a Student's t-test showed insignificant differences,. The biological activity of tested fungal extracts displayed a similar behavioral effect compared to the experiments in which only pure psilocin has been used, despite the fact that the amount of psilocin present in extracts was at much lower concentration level.

Published By:

O Zhuk, I Jasicka-Misiak, A Poliwoda, A Kazakova… - Toxins, 2015 - mdpi.com

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42

After the mixture was stirred for 2 h at room temperature, H2O was added, and the mixture was evaporated in vacuo. To a suspension of lithium aluminum hydride in anhydrous tetrahydofuran under an argon atmosphere was dropwise added a solution of 6 in anhydrous tetrahydofuran over 2 h, and then the reaction mixture was refluxed for 2 h. After cooling, anhydrous Na2SO4 powder was added, and then a solution of saturated Na2SO4 was dropwise added Notes over 1 h with stirring at room temperature.

Published By:

O Shirota, W Hakamata, Y Goda - Journal of natural products, 2003 - ACS Publications

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82

With good in process control by HPLC for reaction monitoring in place, it was determined that after LiAlH4 addition at 0 °C and subsequent warming to ambient temperature, only the major intermediate and approximately 5% of 7 was present in the reaction mixture. The solid CO2 /acetone cooing bath was removed and the temperature was allowed to slowly rise to -25 °C over 2 h, at which time LCMS showed completion of the reaction to compound 15 with no trace of compound 10 in the reaction mixture.

Published By:

AM Sherwood, P Meisenheimer, G Tarpley… - Synthesis, 2020 - thieme-connect.com

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15

The reported pH of a solution of psilocybin in 50% aqueous ethanol is 5.2.9 Anion exchange resin was added in portions, with vigorous and extended stirring, to the filtered reaction solution until the pH of the solution was 5.2. 4-Benzyloxyindol-3-yl-N,N-dimethylglyoxylamide A solution of 4-benzyloxyindole in anhyd Et2O was mechanically stirred in a 1 L, 3 necked flask and cooled in an ice-salt bath to an internal temperature of 0 °C. Oxalyl chloride was added dropwise at a rate that maintained an internal temperature between 0-5 °C. Stirring was continued for 3 h at a temperature between 5-10 °C with a gentle argon sparge to remove evolved HCl. The argon sparge was replaced by a gas inlet tube and a dry ice/acetone condenser.

Published By:

DE Nichols, S Frescas - Synthesis, 1999 - thieme-connect.com

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62

Fractions 85-149 were combined as were Fractions 150-305. The procedures followed were identical with those described except that i t was nccessary to chromatograph Fraction 2 on a cellulose column prior t o combining this fraction with the mother liquid of Fraction 1, in order to free i t of glycine.

Published By:

AY Leung, AG Paul - Journal of Pharmaceutical Sciences, 1968 - Elsevier

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98

The article discusses the pharmacology of psilocybin, the active principle of Psilocybe mexicana Heim. The study found that psilocybin did not have marked effects on isolated organs such as the seminal vesicle, intestine, and auricle of guinea pigs or the uterus of rats. However, it did produce slight sympathetic stimulation in vivo, with effects such as mydriasis, tachycardia, and hyperthermia in unanaesthetized rabbits. The study also found that psilocybin affected blood pressure and heart rate in anaesthetized cats and dogs, with the effect depending on dosage and species. The motor activity of mice, rabbits, and monkeys was largely unaffected or slightly depressed, but psilocybin did enhance spinal reflexes in cats. The article concludes that although psilocybin has effects on certain physiological functions, it is not a potent drug in terms of its effects on motor activity. Overall, the study offers insight into the pharmacological properties of psilocybin, which could be useful for further research and development of the drug.

Published By:

H Weidmann, M Taeschler, H Konzett - Experientia, 1958 - Springer

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36

Researchers have successfully used DNA-based techniques to identify the biological material contained in the culture media of hallucinogenic mushrooms. This has been found to be an effective approach for the forensic identification of illegal samples, particularly those mixed in with spores where spore-bearing fruiting bodies are not present. This method enables potentially illicit material to be identified before cultivation and stopped at customs, preventing the need for a criminal case to be built. Despite psilocin and psilocybin being illegal in many countries, the law remains unclear regarding the legality of "grow-kits" containing spores. To confirm their findings, scientists also developed a reliable method for the forensic identification of psilocin and psilocybin in hallucinogenic mushrooms using liquid chromatography-ultraviolet (LC-UV) techniques.

Published By:

A Horita, LJ Weber - Toxicology and Applied Pharmacology, 1962 - Elsevier

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50