Back سيلوسين Arabic سیلوسین AZB Psilocin Czech Psilocin German Psilocino Esperanto Psilocina Spanish Psilozina Basque سیلوسین Persian Psilosiini Finnish Psilocine French
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| Other names | Psilocine; Psilocyn; Psilotsin; 4-Hydroxy-N,N-dimethyltryptamine; 4-Hydroxy-DMT; 4-Hydroxy-N,N-DMT; 4-HO-DMT; 4-OH-DMT; PSOH; PAL-153; PAL153; CX-59; CX59 |
| Routes of administration | By mouth, intravenous[1] |
| Drug class | Serotonergic psychedelic; Hallucinogen; Serotonin receptor agonist[2] |
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| Pharmacokinetic data | |
| Bioavailability | Oral psilocybin: 52.7 ± 20.4% (as psilocin)[2][1] |
| Metabolism | Liver, other tissues:[5][2][1][6] • Demethylation and deamination (MAO) • Oxidation (ALDH) • Glucuronidation (UGTs) |
| Metabolites | • Psilocin-O-glucuronide[2][1] • 4-Hydroxy-indole-3-acetaldehyde[2][1] • 4-Hydroxyindole-3-acetic acid (4-HIAA)[2][1] • 4-Hydroxytryptophol[2][1] |
| Elimination half-life | Oral psilocybin: 2.3–3 hours (as psilocin)[2][1][4] IV psilocybin: 1.2 hours (as psilocin)[1][4] |
| Excretion | Urine (mainly as psilocin-O-glucuronide, 2–4% unchanged)[2][1][4] |
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| ECHA InfoCard | 100.007.543 |
| Chemical and physical data | |
| Formula | C12H16N2O |
| Molar mass | 204.273 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 173 to 176 °C (343 to 349 °F) |
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Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms[7] together with its phosphorylated counterpart psilocybin. Psilocybin, as well as synthetic esters such as 4-AcO-DMT (psilacetin; O-acetylpsilocin) and 4-PrO-DMT (O-propionylpsilocin), are prodrugs of psilocin.
Acting on the serotonin 5-HT2A receptors, psilocin's psychedelic effects are directly correlated with the drug's occupancy at these receptor sites.[8] It also interacts with other serotonin receptors and targets. The subjective mind-altering effects of psilocin are highly variable in their qualitative nature but resemble those of lysergic acid diethylamide (LSD) and N,N-dimethyltryptamine (DMT).
Psilocin is a Schedule I drug under the Convention on Psychotropic Substances.[9]
- ^ a b c d e f g h i j Cite error: The named reference
LoweToyangSteele2021was invoked but never defined (see the help page). - ^ a b c d e f g h i Dodd S, Norman TR, Eyre HA, Stahl SM, Phillips A, Carvalho AF, Berk M (July 2022). "Psilocybin in neuropsychiatry: a review of its pharmacology, safety, and efficacy". CNS Spectr. 28 (4): 416–426. doi:10.1017/S1092852922000888. PMID 35811423.
- ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
- ^ a b c Cite error: The named reference
TylšPáleníčekHoráček2014was invoked but never defined (see the help page). - ^ MacCallum CA, Lo LA, Pistawka CA, Deol JK (2022). "Therapeutic use of psilocybin: Practical considerations for dosing and administration". Frontiers in Psychiatry. 13: 1040217. doi:10.3389/fpsyt.2022.1040217. PMC 9751063. PMID 36532184.
- ^ Coppola M, Bevione F, Mondola R (February 2022). "Psilocybin for Treating Psychiatric Disorders: A Psychonaut Legend or a Promising Therapeutic Perspective?". Journal of Xenobiotics. 12 (1): 41–52. doi:10.3390/jox12010004. PMC 8883979. PMID 35225956.
- ^ Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences. 23 (22): 14068. doi:10.3390/ijms232214068. PMC 9693126. PMID 36430546.
- ^ Madsen MK, Fisher PM, Burmester D, Dyssegaard A, Stenbæk DS, Kristiansen S, et al. (June 2019). "Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels". Neuropsychopharmacology. 44 (7): 1328–1334. doi:10.1038/s41386-019-0324-9. PMC 6785028. PMID 30685771.
- ^ "List of psychotropic substances under international control" (PDF) (23rd ed.). Vienna Austria: International Narcotics Control Board. August 2003. Archived from the original (PDF) on 4 February 2012. Retrieved 2012-10-11.