Literature DB >> 33667102

Chemoenzymatic Synthesis of 5-Methylpsilocybin: A Tryptamine with Potential Psychedelic Activity.

Janis Fricke1, Alexander M Sherwood2, Adam L Halberstadt3,4, Robert B Kargbo2, Dirk Hoffmeister1.   

Abstract

A novel analogue of psilocybin was produced by hybrid chemoenzymatic synthesis in sufficient quantity to enable bioassay. Utilizing purified 4-hydroxytryptamine kinase from Psilocybe cubensis, chemically synthesized 5-methylpsilocin (2) was enzymatically phosphorylated to provide 5-methylpsilocybin (1). The zwitterionic product was isolated from the enzymatic step with high purity utilizing a solvent-antisolvent precipitation approach. Subsequently, 1 was tested for psychedelic-like activity using the mouse head-twitch response assay, which indicated activity that was more potent than the psychedelic dimethyltryptamine, but less potent than that of psilocybin.

Entities:  

Mesh：

Substances：

Year:  2021        PMID： 33667102      PMCID： PMC9191645          DOI： 10.1021/acs.jnatprod.1c00087

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.803


  27 in total

1.  A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.

Authors:  M M Bradford
Journal:  Anal Biochem       Date:  1976-05-07       Impact factor: 3.365

2.  Enzymatic Route toward 6-Methylated Baeocystin and Psilocybin.

Authors:  Janis Fricke; Alexander Sherwood; Robert Kargbo; Andrew Orry; Felix Blei; Andreas Naschberger; Bernhard Rupp; Dirk Hoffmeister
Journal:  Chembiochem       Date:  2019-10-17       Impact factor: 3.164

3.  Psychedelic Psychiatry's Brave New World.

Authors:  David Nutt; David Erritzoe; Robin Carhart-Harris
Journal:  Cell       Date:  2020-04-02       Impact factor: 41.582

4.  Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs.

Authors:  Landon M Klein; Nicholas V Cozzi; Paul F Daley; Simon D Brandt; Adam L Halberstadt
Journal:  Neuropharmacology       Date:  2018-02-27       Impact factor: 5.250

Review 5.  Taking Different Roads: l-Tryptophan as the Origin of Psilocybe Natural Products.

Authors:  Claudius Lenz; Alexander Sherwood; Robert Kargbo; Dirk Hoffmeister
Journal:  Chempluschem       Date:  2020-11-25       Impact factor: 2.863

6.  Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents.

Authors:  D B Repke; D B Grotjahn; A T Shulgin
Journal:  J Med Chem       Date:  1985-07       Impact factor: 7.446

7.  Serotonin 2A Receptor Signaling Underlies LSD-induced Alteration of the Neural Response to Dynamic Changes in Music.

Authors:  Frederick S Barrett; Katrin H Preller; Marcus Herdener; Petr Janata; Franz X Vollenweider
Journal:  Cereb Cortex       Date:  2018-11-01       Impact factor: 5.357

Review 8.  Efficacy, tolerability, and safety of serotonergic psychedelics for the management of mood, anxiety, and substance-use disorders: a systematic review of systematic reviews.

Authors:  Rafael G Dos Santos; José Carlos Bouso; Miguel Ángel Alcázar-Córcoles; Jaime E C Hallak
Journal:  Expert Rev Clin Pharmacol       Date:  2018-08-23       Impact factor: 5.045

9.  Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species.

Authors:  Adam L Halberstadt; Muhammad Chatha; Adam K Klein; Jason Wallach; Simon D Brandt
Journal:  Neuropharmacology       Date:  2020-01-07       Impact factor: 5.273
View more
  1 in total

1.  Enlightening the "Spirit Molecule": Photomodulation of the 5-HT2A Receptor by a Light-Controllable N,N-Dimethyltryptamine Derivative.

Authors:  Hubert Gerwe; Feng He; Eline Pottie; Christophe Stove; Michael Decker
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-29       Impact factor: 16.823
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.