Cited by 225Forensic Toxicology and Drug AnalysisPsychedelics and Drug StudiesPharmacogenetics and Drug Metabolism

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Metabolism of psilocybin and psilocin: clinical and forensic toxicological relevance

Dinis-Oliveira, Ricardo Jorge·2017·Drug Metabolism Reviews

DOI 10.1080/03602532.2016.1278228

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Abstract

Psilocybin and psilocin are controlled substances in many countries. These are the two main hallucinogenic compounds of the “magic mushrooms” and both act as agonists or partial agonists at 5-hydroxytryptamine (5-HT)2A subtype receptors. During the last few years, psilocybin and psilocin have gained therapeutic relevance but considerable physiological variability between individuals that can influence dose-response and toxicological profile has been reported. This review aims to discuss metabolism of psilocybin and psilocin, by presenting all major and minor psychoactive metabolites. Psilocybin is primarily a pro-drug that is dephosphorylated by alkaline phosphatase to active metabolite psilocin. This last is then further metabolized, psilocin-O-glucuronide being the main urinary metabolite with clinical and forensic relevance in diagnosis.

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“001), and significant main effects of time (F(1,20) = 4.”
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“When metabolized in the bloodstream by alkaline phosphatases, it is converted to its active form, psilocin (Dinis-Oliveira, 2017).”
Do the therapeutic effects of psilocybin involve actions in the gut?
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“A. muscaria contains many biologically active compounds including the psychoactive alkaloids: muscarine, ibotenic acid and muscimol [109] where ibotenic and muscimol are structurally similar to gamma-aminobutyric acid (GABA) having effect on glutamate receptors in the CNS [110] and can cross the BBB. Ibotenic acid is…”
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“As a substituted indolealkylamine it is based upon the structure of tryptamine, illustrated in Figure 2, which acts as a predominant agonist in the serotonergic system at 5-hydroxytryptamine (5-HT) 1a and 2a/c subtype receptors [7].”
Abuse of Licit and Illicit Psychoactive Substances in the Workplace: Medical, Toxicological, and Forensic Aspects
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“Hallucinogens, such as the diethylamide of lysergic acid (LSD), mescaline, psilocybin, and psilocin, also have a pronounced effect on workplace performance [52,53].”
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Novel Psilocin Prodrugs with Altered Pharmacological Properties as Candidate Therapies for Treatment-Resistant Anxiety Disorders
Raithatha, S. A., Hagel, J. M., Matinkhoo, K., Yu, L. X., Press, D., Cook, S. G., Sharma, G., Dhananjaya, D., Jensen, G., Lee, J. B., et al. (2023) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.3c01225 · Cited by 23
Abuse of Magic Mushroom, Peyote Cactus, LSD, Khat, and Volatiles
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“In summary, metabolism occurs by dephosphorylation in the stomach by alkaline phosphatases or other non-specific esterases in the intestine and kidneys [11–14].”
Psychedelics and Psychedelic-Assisted Psychotherapy
Reiff, C. M., Richman, E. E., Nemeroff, C. B., Carpenter, L. L., Widge, A. S., Rodríguez, C. I., Kalin, N. H., & McDonald, W. M. (2021) · FOCUS The Journal of Lifelong Learning in Psychiatry · doi:10.1176/appi.focus.19104 · Cited by 28
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Haniff, Z. R., Bocharova, M., Mantingh, T., Rucker, J., Velayudhan, L., Taylor, D. M., Young, A. H., Aarsland, D., Vernon, A. C., & Thuret, S. (2024) · Pharmacology & Therapeutics · doi:10.1016/j.pharmthera.2024.108641 · Cited by 21
“There is, however, evidence that it may bind other 5-HT receptor subtypes, receptor classes and monoamine transporters to a lesser extent (Blough et al., 2014; Dinis-Oliveira, 2017; Erkizia-Santamaría, Alles-Pascual, Horrillo, Meana, & Ortega, 2022a; Halberstadt & Geyer, 2011).”
Bis(4-acetoxy-N,N-dimethyltryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
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“When consumed orally, psilocybin hydrolyzes to generate psilocin, a serotonin-2a agonist, producing mood-altering or ‘psychedelic’ effects (Dinis-Oliveira, 2017).”
Background
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“Future studies should also consider other important factors that may alter the metabolic pathway of psilocin, including the enzymes aldehyde dehydrogenase and uridine diphosphate (UDP)- glucuronosyltransferases (Dinis-Oliveira, 2017) which may be affected by chronic alcohol intake.”
Chronic Treatment With Psilocybin Decreases Changes in Body Weight in a Rodent Model of Obesity
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“Its active form, psilocin (4-hydroxy-N,N-dimethyltryptamine) is a serotoninergic agonist [15] that binds to (5-HT)2A receptors causing the above-mentioned effects [16].”
Background
Cardiovascular effects and safety of classic psychedelics
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“56); and the distinct metabolic profile of each compound 57,58 .”
Molecular and Medical Aspects of Psychedelics
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Efficacy and safety of psilocybin for the treatment of substance use disorders: A systematic review
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Interpol review of controlled substances 2016–2019
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“[786]; review [787]; characterization of four psilocybin biosynthesis enzymes [788]; 1D and 2D NMR spectroscopy and high-”
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Deciphering psilocybin: Cytotoxicity, anti-inflammatory effects, and mechanistic insights
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Immunochemical monitoring of psilocybin and psilocin to identify hallucinogenic mushrooms
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“The elimination half-life of psilocin is approximately 50 min, with psychoactive effects typically lasting 4 – 6 h, depending on the dose and metabolism (Dinis-Oliveira, 2017).”
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“These metabolites are excreted by the liver and kidney, however, enzymes involved in these reactions are unknown (Brown et al., 2017; Dinis-Oliveira, 2017).”
Background
A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines
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“These effects encompass changes in neurotransmitter release, notably dopamine and glutamate, and can modulate perception, emotions, thoughts, and symptoms of anxiety or elation (Dinis-Oliveira, 2017; López-Giménez and González-Maeso, 2018).”
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“7 The half-life of psilocin is 108 minutes.”
Background
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“However, both psilocybin and psilocin have been found to be soluble in methanol and ethanol (Dinis-Oliveira 2017).”
Background
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“After consumption, psilocybin is rapidly metabolized to psilocin (4-OH-DMT) by intestinal alkaline phosphates and undetermined esterases [134], as illustrated in Fig.”
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“43 In fact, MAO inhibitors (MAOIs) are also consumed with psilocybin to intensify its effects 42 and hy-pothetically, CYP2D6 activity could influence the effects of this combination.”
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“Psilocin crosses the blood–brain barrier and directly binds with 5-HT receptors (5-HTRs) (Dinis-Oliveira 2017).”
Background
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“The psychoactive effects of psilocin usually subside within about four to six hours after it is excreted from the body [51].”
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“On oral administration in humans, psilocybin is rapidly converted to psilocin via intestinal alkaline phosphatase, where nearly 100% of the bioactive molecule is found in circulation 30 min to 6 h after ingestion (Dinis-Oliveira, 2017).”
Background
Content analysis of Reddit posts about coadministration of selective serotonin reuptake inhibitors and psilocybin mushrooms
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“Sixth, it is possible that there are meaningful differences between the synthetic psilo-cybin used in research settings and the psilocybin mush-rooms accessible in the community–few data are available regarding other psychoactive compounds found in mush-rooms (Dinis-Oliveira 2017).”
The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin
Chadeayne, A. R., Pham, D. N. K., Golen, J. A., & Manke, D. R. (2019) · Acta Crystallographica Section E Crystallographic Communications · doi:10.1107/s2056989019011253 · Cited by 12
“Upon digestion, psilocybin hydrolyses to generate psilocin, the 4-hydroxy derivative of DMT. Psilocin is a potent seratonin 2a-agonist, which is responsible for its psychoactive properties (Dinis-Oliveira, 2017; Nichols, 2012).”
Background
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“Psilocybin is dephosphorylated to the active metabolite psilocin by systemic alkaline phosphatase after peripheral administration [11, 38].”
Background
Medicinal Mushroom of Potential Pharmaceutical Toxic Importance: Contribution in Phytotherapy
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“Many NPs present structural similarities with certain endogenous compounds [2].”
Background
Effects of psilocybin, the 5-HT2A receptor agonist TCB-2, and the 5-HT2A receptor antagonist M100907 on visual attention in male mice in the continuous performance test
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“Pharmacologically, psilocybin activates serotonin (5-HT) 2A receptors via its active metabolite psilocin (Dinis-Oliveira 2017).”
In vivo validation of psilacetin as a prodrug yielding modestly lower peripheral psilocin exposure than psilocybin
Jones, N., Wagner, L., Pellitteri-Hahn, M. C., Scarlett, C. O., & Wenthur, C. J. (2024) · Frontiers in Psychiatry · doi:10.3389/fpsyt.2023.1303365 · Cited by 12

Authors: Dinis-Oliveira, R. J.
Affiliations: Department of Sciences, IINFACTS – Institute of Research and Advanced Training in Health Sciences and Technologies, University Institute of Health Sciences (IUCS), CESPU, CRL, Gandra, Portugal;
Venue: Drug Metabolism Reviews
Publisher: Informa UK Limited
Published: 2017-01-02
Volume: 49
Issue: 1
Pages: 84-91
ISSN: 0360-2532 (ISSN-L)
1097-9883
DOI: 10.1080/03602532.2016.1278228
OpenAlex: W2572835720
Cited by: 224
References: 65
Citations by year: 2026: 21 · 2025: 48 · 2024: 41 · 2023: 38 · 2022: 36 · 2021: 10 · 2020: 17 · 2019: 7 · 2018: 6
FWCI: 1.17
Type: journal article
Language: en
Open access: closed
Locations: Drug Metabolism Reviews (publishedVersion)
PubMed (publishedVersion)
Funders: Fundação para a Ciência e a Tecnologia
FCT (IF/01147/2013)
FEDER (UID/QUI/50006/2013)
Topics: Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
Social Sciences › Psychology › Clinical Psychology › Psychedelics and Drug Studies
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
Keywords: psilocybin, psilocin, drug metabolism, alkaline phosphatase, prodrugs, urinary metabolites, forensic toxicology, clinical toxicology, 5-HT2A receptor agonists, magic mushrooms, hallucinogens
MeSH terms: Hallucinogens, Humans, Prodrugs, Psilocybin, Metabolomics

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Metabolism of psilocybin and psilocin: clinical and forensic toxicological relevance

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