Psilocybin and psilocin research index

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Structure-Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice.

4-Phosphoryloxy-N,N-dimethyltryptamine (psilocybin) is a naturally occurring tertiary amine found in many mushroom species. Psilocybin is a prodrug for 4-hydroxy-N,N-dimethyltryptamine (psilocin), which induces psychedelic effects via agonist activity at the serotonin (5-HT) 2A receptor (5-HT2A). Several other 4-position ring-substituted tryptamines are pres...

Details DOI 10.1021/acsptsci.2c00177 PubMed 36407948 Copy citation Copy BibTeX

ACS Pharmacology & Translational Science 2022-11-01 Glatfelter GC, Pottie E, Partilla JS, Sherwood AM, Kaylo K, Pham DNK

Europe PMC Published psilocybinpsilocin Receptor PharmacologyAnimal StudyIn Vitro Study Animal Study More

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3,4-Methylenedioxy methamphetamine, synthetic cathinones and psychedelics: From recreational to novel psychotherapeutic drugs.

The utility of classical drugs used to treat psychiatric disorders (e.g., antidepressants, anxiolytics) is often limited by issues of lack of efficacy, delayed onset of action or side effects. Psychoactive substances have a long history of being used as tools to alter consciousness and as a gateway to approach the unknown and the divinities. These substances...

Details DOI 10.3389/fpsyt.2022.990405 PubMed 36262632 Copy citation Copy BibTeX

Unknown journal 2022-10-02 López-Arnau R, Camarasa J, Carbó ML, Nadal-Gratacós N, Puigseslloses P, Espinosa-Velasco M

Europe PMC Published psilocybin DepressionPTSDMechanism of Action Review Article More

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A Review of Aeruginascin and Potential Entourage Effect in Hallucinogenic Mushrooms

Introduction The 5-HT2A agonist classic psychedelic, psilocybin (O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine) is a tryptophan, indole-based alkaloid present in up to 2% of certain hallucinogenic “magic” mushroom species; typically Psilocybe azurescens, semilanceata, and cyanescens,. In addition, mushrooms may contain psilocin (4-hydroxy-N,N-dimethyltryptam...

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Unknown journal 2022-08-31 Chue P, Andreiev A, Bucuci E, Els C, Chue J.

Europe PMC Published psilocybinpsilocin PharmacologyReceptor PharmacologyEpigenetics Review Article More

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Synthesis, Structural Characterization, and Pharmacological Activity of Novel Quaternary Salts of 4-Substituted Tryptamines.

Aeruginascin (4-phosphoryloxy-N,N,N-trimethyltryptammonium) is an analogue of psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) that has been identified in several species of psilocybin-containing mushrooms. Our team previously reported the synthesis, structural characterization, and biological activity of the putative metabolite of aeruginascin (4-hydroxy...

Details DOI 10.1021/acsomega.2c03476 PubMed 35874244 Copy citation Copy BibTeX

ACS Omega 2022-07-04 Glatfelter GC, Pham DNK, Walther D, Golen JA, Chadeayne AR, Baumann MH

Europe PMC Published psilocybin Receptor PharmacologyAnimal StudyIn Vitro Study Animal Study More

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Genetic Survey of Psilocybe Natural Products.

Psilocybe magic mushrooms are best known for their main natural product, psilocybin, and its dephosphorylated congener, the psychedelic metabolite psilocin. Beyond tryptamines, the secondary metabolome of these fungi is poorly understood. The genomes of five species (P. azurescens, P. cubensis, P. cyanescens, P. mexicana, and P. serbica) were browsed to unde...

Details DOI 10.1002/cbic.202200249 PubMed 35583969 Copy citation Copy BibTeX

ChemBioChem 2022-06-08 Dörner S, Rogge K, Fricke J, Schäfer T, Wurlitzer JM, Gressler M

Europe PMC Published psilocybinpsilocin Observational StudyGenomicsMetabolomics Observational Study Hallucinogens More

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Assessment of Bioactivity-Modulating Pseudo-Ring Formation in Psilocin and Related Tryptamines.

Psilocybin (1) is the major alkaloid found in psychedelic mushrooms and acts as a prodrug to psilocin (2, 4-hydroxy-N,N-dimethyltryptamine), a potent psychedelic that exerts remarkable alteration of human consciousness. In contrast, the positional isomer bufotenin (7, 5-hydroxy-N,N-dimethyltryptamine) differs significantly in its reported pharmacology. A ser...

Details DOI 10.1002/cbic.202200183 PubMed 35483009 Copy citation Copy BibTeX

ChemBioChem 2022-05-17 Lenz C, Dörner S, Trottmann F, Hertweck C, Sherwood A, Hoffmeister D.

Europe PMC Published psilocybinpsilocin DepressionPharmacologyConsciousness Other Humans More

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Tentative identification of in vitro metabolites of O-acetylpsilocin (psilacetin, 4-AcO-DMT) by UHPLC-Q-Orbitrap MS.

4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT, psilacetin, O-acetylpsilocin) is a synthetic tryptamine with psychedelic properties. Psilacetin may also act as precursor drug of psilocin, similar to psilocybin, but little is known about its metabolism. In this study, the phase I and phase II in vitro metabolism of 4-AcO-DMT was investigated with pooled human li...

Details DOI 10.1002/dta.3255 PubMed 35312166 Copy citation Copy BibTeX

Drug Testing and Analysis 2022-03-28 Zhai W, Li L, Zhao J, Xiang P, Liu M, Shi Y

Europe PMC Published psilocybinpsilocin PharmacologyBiomarkersEpigenetics Clinical Trial Microsomes More

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Effects of the 5-HT2A receptor antagonist volinanserin on head-twitch response and intracranial self-stimulation depression induced by different structural classes of psychedelics in rodents.

BackgroundClinical studies suggest that psychedelics exert robust therapeutic benefits in a number of psychiatric conditions including substance use disorder. Preclinical studies focused on safety and efficacy of these compounds are necessary to determine the full range of psychedelics' effects.ObjectivesThe present study explores the behavioral pharmacology...

Details DOI 10.1007/s00213-022-06092-x PubMed 35233648 Copy citation Copy BibTeX

Unknown journal 2022-03-01 Jaster AM, Elder H, Marsh SA, de la Fuente Revenga M, Negus SS, González-Maeso J.

Europe PMC Published psilocybin DepressionAddictionPharmacology Animal Study Animals More

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From psychiatry to neurology: Psychedelics as prospective therapeutics for neurodegenerative disorders.

The studies of psychedelics, especially psychedelic tryptamines like psilocybin, are rapidly gaining interest in neuroscience research. Much of this interest stems from recent clinical studies demonstrating that they have a unique ability to improve the debilitating symptoms of major depressive disorder (MDD) long-term after only a single treatment. Indeed, ...

Details DOI 10.1111/jnc.15509 PubMed 34519052 Copy citation Copy BibTeX

Unknown journal 2021-10-21 Kozlowska U, Nichols C, Wiatr K, Figiel M.

Europe PMC Published psilocybin DepressionAddictionNeuroplasticity Clinical Trial Humans More

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Psychedelics: A new era of treatment?

Introduction Psychedelics - including LSD (lysergic acid diethylamide), psilocybin, DMT (N, N-dimethyltryptamine), ayahuasca and mescaline - have an ancient history across various civilizations. In 1950, after LSD’s discovery by Hofmann, psychedelics enjoyed a short-lived relationship with psychiatry, before prohibitive legislature emerging in response to th...

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Unknown journal 2021-08-12 Torres S.

Europe PMC Published psilocybin DepressionAnxietyAddiction Randomized Controlled Trial More

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Pharmacologic Similarities and Differences Among Hallucinogens.

Hallucinogens constitute a unique class of substances that cause changes in the user's thoughts, perceptions, and mood through various mechanisms of action. Although the serotonergic hallucinogens such as lysergic acid diethylamide, psilocybin, and N,N-dimethyltryptamine have been termed the classical hallucinogens, many hallucinogens elicit their actions th...

Details DOI 10.1002/jcph.1917 PubMed 34396556 Copy citation Copy BibTeX

The Journal of Clinical Pharmacology 2021-07-31 Waters K.

Europe PMC Published psilocybin AddictionEnd-of-Life DistressMechanism of Action Review Article Humans More

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

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 enzymati...

Details DOI 10.1021/acs.jnatprod.1c00087 PubMed 33667102 Copy citation Copy BibTeX

Journal of Natural Products 2021-03-04 Fricke J, Sherwood AM, Halberstadt AL, Kargbo RB, Hoffmeister D.

Europe PMC Published psilocybin Animal Study Animal Study Animals More

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Chemistry and Toxicology of Major Bioactive Substances in Inocybe Mushrooms.

Mushroom poisoning has always been a threat to human health. There are a large number of reports about ingestion of poisonous mushrooms every year around the world. It attracts the attention of researchers, especially in the aspects of toxin composition, toxic mechanism and toxin application in poisonous mushroom. Inocybe is a large genus of mushrooms and co...

Details DOI 10.3390/ijms22042218 PubMed 33672330 Copy citation Copy BibTeX

Unknown journal 2021-02-22 Patocka J, Wu R, Nepovimova E, Valis M, Wu W, Kuca K.

Europe PMC Published psilocybinpsilocin Mechanism of ActionReview ArticleToxicity Review Article Animals More

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Investigation of the Structure-Activity Relationships of Psilocybin Analogues

The 5-HT2A receptor is thought to be the primary target for psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) and other serotonergic hallucinogens (psychedelic drugs). Although a large amount of experimental work has been conducted to characterize the pharmacology of psilocybin and its dephosphorylated metabolite psilocin (4-hydroxy-N,N-dimethyltryptamine)...

Details DOI 10.1021/acsptsci.0c00176 PubMed 33860183 Copy citation Copy BibTeX

ACS Pharmacology & Translational Science 2020-12-13 Adam K. Klein, Muhammad Chatha, Lauren J. Laskowski, Emilie I. Anderson, Simon D. Brandt, Stephen J. Chapman

OpenAlex Published psilocybinpsilocin PharmacologyReceptor PharmacologyAnimal Study Animal Study Psilocybin More

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

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 ...

Details DOI 10.1002/dta.2950 PubMed 33119971 Copy citation Copy BibTeX

Drug Testing and Analysis 2020-10-28 Klára Gotvaldová, Kateřina Hájková, Jan Borovička, Radek Jurok, Petra Cihlářová, Martin Kuchař

OpenAlex Published psilocybinpsilocin PharmacologyReceptor PharmacologyMicrodosing Other Tryptamine More

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UHPLC-MS/MS method for simultaneously detecting 16 tryptamines and their metabolites in human hair and applications to real forensics cases.

Tryptamines are hallucinogenic substances many of which have appeared recently as novel psychoactive substances (NPS). Herein, we describe the establishment of a rapid UHPLC-MS/MS quantitative method for the targeted screening of 16 tryptamines of abuse in hair. Twenty milligram pieces of hair were pulverized below 4 °C in 0.5 mL of deionized water containin...

Details DOI 10.1016/j.jchromb.2020.122392 PubMed 33126071 Copy citation Copy BibTeX

Unknown journal 2020-10-15 Shi Y, Wang R, Yuan S, Qiang H, Shen M, Shen B

Europe PMC Published psilocybinpsilocin General Other Hair More

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The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin

The solid-state structures of the salts of two substituted tryptamines, namely N -isopropyl- N -methyltryptaminium (MiPT) fumarate {systematic name: [2-(1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate}, C14 H21 N2 + ·C4 H3 O4 −, and 4-hydroxy- N -isopropyl- N -methyltryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4...

Details DOI 10.1107/s2056989019011253 PubMed 31523457 Copy citation Copy BibTeX

Acta Crystallographica Section E Crystallographic Communications 2019-08-14 A.R. Chadeayne, Duyen N. K. Pham, James A. Golen, David R. Manke

OpenAlex Published psilocin General Other Chemistry More

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Iterative l-Tryptophan Methylation in Psilocybe Evolved by Subdomain Duplication.

Psilocybe mushrooms are best known for their l-tryptophan-derived psychotropic alkaloid psilocybin. Dimethylation of norbaeocystin, the precursor of psilocybin, by the enzyme PsiM is a critical step during the biosynthesis of psilocybin. However, the "magic" mushroom Psilocybe serbica also mono- and dimethylates l-tryptophan, which is incompatible with the s...

Details DOI 10.1002/cbic.201800336 PubMed 30098085 Copy citation Copy BibTeX

ChemBioChem 2018-10-01 Blei F, Fricke J, Wick J, Slot JC, Hoffmeister D.

Europe PMC Published psilocybin PharmacologyMechanism of ActionEpigenetics In Vitro Study Tryptamines More

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Psychoactive substances as a last resort-a qualitative study of self-treatment of migraine and cluster headaches.

BackgroundTreatment resistant cluster headache and migraine patients are exploring alternative treatments online. The aim of this study was to improve comprehension regarding the use of non-established or alternative pharmacological treatments used by sufferers of cluster headaches and migraines.MethodsA qualitative thematic analysis of the users' own accoun...

Details DOI 10.1186/s12954-017-0186-6 PubMed 28870224 Copy citation Copy BibTeX

Harm Reduction Journal 2017-09-04 Andersson M, Persson M, Kjellgren A.

Europe PMC Published psilocybin Headache / MigraineSafetyAdverse Events Qualitative Study Humans More

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Proposal of 5-methoxy-N-methyl-N-isopropyltryptamine consumption biomarkers through identification of in vivo metabolites from mice.

New psychoactive substances (NPS) are a new breed of synthetically produced substances designed to mimic the effects of traditional illegal drugs. Synthetic cannabinoids and synthetic cathinones are the two most common groups, which try to mimic the effects of the natural compounds 9Δ-tetrahydrocannabinol and cathinone, respectively. Similarly, synthetic try...

Details DOI 10.1016/j.chroma.2017.06.010 PubMed 28602505 Copy citation Copy BibTeX

Unknown journal 2017-06-04 Fabregat-Safont D, Barneo-Muñoz M, Martinez-Garcia F, Sancho JV, Hernández F, Ibáñez M.

Europe PMC Published psilocin PharmacologyBiomarkersAnimal Study Animal Study Animals More