Chemical compound
Psilocin Other names Psilocine; Psilocyn; Psilotsin; 4-Hydroxy-N ,N -dimethyltryptamine; 4-Hydroxy-DMT; 4-Hydroxy-N ,N -DMT; 4-OH-DMT; 4-HO-DMT Routes of administration Oral , intravenous [ 1] Drug class Serotonin receptor agonist ; Serotonin 5-HT2A receptor agonist ; Serotonergic psychedelic ; Hallucinogen ; Entheogen [ 2] ATC code Legal status
Bioavailability Oral psilocybin : 52.7 ± 20.4% (as psilocin) (n=3)[ 2] [ 1] Metabolism Liver , other tissues :[ 5] [ 2] [ 1] [ 6] • Demethylation (MAO Tooltip monoamine oxidase ) • Oxidation (ALDH Tooltip aldehyde dehydrogenase ) • Glucuronidation (UGTs )Metabolites • 4-Hydroxyindole-3-acetic acid (4-HIAA)[ 2] [ 1] • 4-Hydroxy-indole-3-acetaldehyde[ 2] [ 1] • 4-Hydroxytryptophol[ 2] [ 1] • Psilocin-O -glucuronide[ 2] [ 1] Elimination half-life Oral psilocybin: 2.3–3 hours (as psilocin)[ 2] [ 1] [ 4] IV Tooltip Intravenous injection psilocybin: 1.2 hours (as psilocin)[ 1] [ 4] Excretion Urine (mainly as psilocin-O -glucuronide, 2–4% unchanged)[ 2] [ 1] [ 4]
3-[2-(Dimethylamino)ethyl]-1H -indol-4-ol
CAS Number PubChem CID IUPHAR/BPS ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.007.543 Formula C 12 H 16 N 2 O Molar mass 204.273 g·mol−1 3D model (JSmol ) Melting point 173 to 176 °C (343 to 349 °F)
CN(C)CCc1c[nH]c2cccc(O)c12
InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3
Y Key:SPCIYGNTAMCTRO-UHFFFAOYSA-N
Y
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Psilocin , also known as 4-hydroxy-N ,N -dimethyltryptamine (4-OH-DMT ), is a substituted tryptamine alkaloid and a serotonergic psychedelic . It is present in most psychedelic mushrooms [ 7] together with its phosphorylated counterpart psilocybin . Psilocin is a Schedule I drug under the Convention on Psychotropic Substances .[ 8] Acting on the serotonin 5-HT2A receptors , psilocin's psychedelic effects are directly correlated with the drug's occupancy at these receptor sites.[ 9] The subjective mind-altering effects of psilocin are highly variable and are said to resemble those of lysergic acid diethylamide (LSD) and N ,N -dimethyltryptamine (DMT).
^ a b c d e f g h i j Lowe H, Toyang N, Steele B, Valentine H, Grant J, Ali A, Ngwa W, Gordon L (May 2021). "The Therapeutic Potential of Psilocybin" . Molecules . 26 (10): 2948. doi :10.3390/molecules26102948 . PMC 8156539 . PMID 34063505 .
^ 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 : 1–11. 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 Tylš F, Páleníček T, Horáček J (March 2014). "Psilocybin--summary of knowledge and new perspectives". European Neuropsychopharmacology . 24 (3): 342–356. doi :10.1016/j.euroneuro.2013.12.006 . PMID 24444771 . S2CID 10758314 .
^ 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 .
^ "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 .
^ 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 .