Psilocin

Psilocin
Skeletal formula
Ball-and-stick model
Clinical data
Other namesPsilocine; 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 classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Entheogen[2]
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral psilocybin: 52.7 ± 20.4% (as psilocin) (n=3)[2][1]
MetabolismLiver, other tissues:[5][2][1][6]
• Demethylation (MAOTooltip monoamine oxidase)
• Oxidation (ALDHTooltip 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-lifeOral psilocybin: 2.3–3 hours (as psilocin)[2][1][4]
IVTooltip Intravenous injection psilocybin: 1.2 hours (as psilocin)[1][4]
ExcretionUrine (mainly as psilocin-O-glucuronide, 2–4% unchanged)[2][1][4]
Identifiers
  • 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.543 Edit this at Wikidata
Chemical and physical data
FormulaC12H16N2O
Molar mass204.273 g·mol−1
3D model (JSmol)
Melting point173 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 checkY
  • Key:SPCIYGNTAMCTRO-UHFFFAOYSA-N checkY
  (verify)

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).

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ "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.
  9. ^ 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.