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Psilocybin

Psilocybin
INN: Psilocybine
Kekulé, skeletal formula of canonical psilocybin
Ball-and-stick model of canonical psilocybin
Clinical data
Pronunciation/ˌsaɪləˈsaɪbɪn/ sy-lə-SY-bin, /ˌsɪl-/
Other namesPsilocybine; Psilocibin; Psylocybin; Psilocybinum; Psilotsibin; Psilocin phosphate; Psilocin phosphate ester; Indocybin; O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine; 4-Phosphoryloxy-N,N-dimethyltryptamine; 4-Phosphoryl-N,N-dimethyltryptamine; 4-PO-DMT; 4-PO-N,N-DMT; COMP-360; COMP360, Psilocybin (USAN US)
Dependence
liability		Low[1][2][3][4][5]
Addiction
liability		Low[1][6]
Routes of
administration
Drug classSerotonergic psychedelic (hallucinogen)[8]
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 52.7 ± 20.4% (as psilocin) (n=3)[10][11][12]
Protein binding66%[13]
MetabolismLiver, other tissues:[11][10][7][16]
• Dephosphorylation (ALPTooltip alkaline phosphatase)
• Demethylation and deamination (MAOTooltip monoamine oxidase)
• Oxidation (ALDHTooltip aldehyde dehydrogenase)
• Glucuronidation (UGTs)
Metabolites• Psilocin[11][10][7]
• Psilocin-O-glucuronide[10][7]
• 4-Hydroxyindole-3-acetaldehyde[10][7]
• 4-Hydroxyindole-3-acetic acid (4-HIAA)[10][7]
• 4-Hydroxytryptophol[10][7]
Onset of actionOral: 20–40 min[11]
Elimination half-lifeOral (as psilocin): 2.1–3.7 hours (range 1.5–18.6 hours)[10]
IVTooltip Intravenous administration (as psilocin): 1.2 hours (range 1.8–4.5 hours)[10][2]
Duration of actionOral: 4–6 hours (range 3–12 hours)[11][14]
IVTooltip Intravenous injection: 15–30 minutes (1 mg, n=6)[2][12]
ExcretionUrine (mainly as psilocin-O-glucuronide, 2–4% as unchanged psilocin)[10][7][15]
Identifiers
  • [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.542 Edit this at Wikidata
Chemical and physical data
FormulaC12H17N2O4P
Molar mass284.252 g·mol−1
3D model (JSmol)
Melting point220–228 °C (428–442 °F) [17]
  • CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
  • InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17) checkY
  • Key:QVDSEJDULKLHCG-UHFFFAOYSA-N checkY
  (verify)

Psilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT), and formerly sold under the brand name Indocybin,[a] is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. Psilocybin is itself biologically inactive but is quickly converted by the body to psilocin, which has mind-altering effects similar, in some aspects, to those of other classical psychedelics. Effects include euphoria, visual and mental hallucinations, changes in perception, a distorted sense of time,[19] and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

Imagery in cave paintings and rock art of modern-day Algeria and Spain suggests that human use of psilocybin mushrooms predates recorded history.[20] In Mesoamerica, the mushrooms had long been consumed in spiritual and divinatory ceremonies before Spanish chroniclers first documented their use in the 16th century. In 1958, the Swiss chemist Albert Hofmann isolated psilocybin and psilocin from the mushroom Psilocybe mexicana. His employer, Sandoz, marketed and sold pure psilocybin to physicians and clinicians worldwide for use in psychedelic therapy. Increasingly restrictive drug laws of the 1960s and the 1970s curbed scientific research into the effects of psilocybin and other hallucinogens, but its popularity as an entheogen (spirituality-enhancing agent) grew in the next decade, owing largely to the increased availability of information on how to cultivate psilocybin mushrooms.

The intensity and duration of psilocybin's effects vary, depending on species or cultivar of mushrooms, dosage, individual physiology, and set and setting, as shown in experiments led by Timothy Leary at Harvard University in the early 1960s. Once ingested, psilocybin is rapidly metabolized to psilocin, which then acts on serotonin receptors in the brain. Psilocybin's mind-altering effects typically last two to six hours, although to people under the influence of psilocybin, they may seem to last much longer, since the drug can distort the perception of time. Possession of psilocybin-containing mushrooms has been outlawed in most countries, and psilocybin has been classified as a Schedule I controlled substance under the 1971 United Nations Convention on Psychotropic Substances.

  1. ^ a b Johnson MW, Griffiths RR, Hendricks PS, Henningfield JE (November 2018). "The abuse potential of medical psilocybin according to the 8 factors of the Controlled Substances Act". Neuropharmacology. 142: 143–166. doi:10.1016/j.neuropharm.2018.05.012. PMC 6791528. PMID 29753748.
  2. ^ a b c Cite error: The named reference Passie2002 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Chen2008 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Amsterdam2010 was invoked but never defined (see the help page).
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  6. ^ Cite error: The named reference Nicholas2006 was invoked but never defined (see the help page).
  7. ^ a b c d e f g h Lowe H, Toyang N, Steele B, Valentine H, Grant J, Ali A, et al. (May 2021). "The Therapeutic Potential of Psilocybin". Molecules. 26 (10): 2948. doi:10.3390/molecules26102948. PMC 8156539. PMID 34063505.
  8. ^ Szafoni S, Gręblowski P, Grabowska K, Więckiewicz G (June 11, 2024). "Unlocking the healing power of psilocybin: an overview of the role of psilocybin therapy in major depressive disorder, obsessive-compulsive disorder and substance use disorder". Frontiers in Psychiatry. 15: 1406888. doi:10.3389/fpsyt.2024.1406888. PMC 11196758. PMID 38919636.
  9. ^ Anvisa (July 24, 2023). "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 July 25, 2023). Archived from the original on August 27, 2023. Retrieved August 27, 2023.
  10. ^ a b c d e f g h i j Dodd S, Norman TR, Eyre HA, Stahl SM, Phillips A, Carvalho AF, et al. (July 2022). "Psilocybin in neuropsychiatry: a review of its pharmacology, safety, and efficacy". CNS Spectrums. 28 (4): 416–426. doi:10.1017/S1092852922000888. PMID 35811423.
  11. ^ a b c d e 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.
  12. ^ a b Hasler F, Bourquin D, Brenneisen R, Bär T, Vollenweider FX (June 1997). "Determination of psilocin and 4-hydroxyindole-3-acetic acid in plasma by HPLC-ECD and pharmacokinetic profiles of oral and intravenous psilocybin in man". Pharm Acta Helv. 72 (3): 175–184. doi:10.1016/s0031-6865(97)00014-9. PMID 9204776.
  13. ^ Čampara A, Kovačić D (2024). "Exploring Psilocybin as a Tool for Studying Parkinsonism-Related Psychosis: A Narrative Review Supplemented with a Computational Approach". MEDICON'23 and CMBEBIH'23. IFMBE Proceedings. Vol. 94. Cham: Springer Nature Switzerland. pp. 530–547. doi:10.1007/978-3-031-49068-2_54. ISBN 978-3-031-49067-5. With a logS value of −3.009 and a plasma protein binding of 0.66, respectively, psilocybin has poor water solubility and is moderately bound to plasma proteins.
  14. ^ Yerubandi A, Thomas JE, Bhuiya NM, Harrington C, Villa Zapata L, Caballero J (April 2024). "Acute Adverse Effects of Therapeutic Doses of Psilocybin: A Systematic Review and Meta-Analysis". JAMA Network Open. 7 (4): e245960. doi:10.1001/jamanetworkopen.2024.5960. PMC 11007582. PMID 38598236. When selecting adverse event profile rates, the shortest time period available was selected and analyzed (eg, day 1 instead of day 30) since the half-life of psilocin is 3 ± 1.1 hours when taken orally and the duration of action can range between 3 to 12 hours.12,13
  15. ^ 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.
  16. ^ 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.
  17. ^ Merck Index, 11th Edition, 7942
  18. ^ Cite error: The named reference Pubchem was invoked but never defined (see the help page).
  19. ^ Siegel JS, Subramanian S, Perry D, Kay BP, Gordon EM, Laumann TO, et al. (August 2024). "Psilocybin desynchronizes the human brain". Nature. 632 (8023): 131–138. Bibcode:2024Natur.632..131S. doi:10.1038/s41586-024-07624-5. PMC 11291293. PMID 39020167.
  20. ^ "Plants of Mind and Spirit - Fungi". July 19, 2022. Archived from the original on July 19, 2022. Retrieved April 24, 2024.{{cite web}}: CS1 maint: bot: original URL status unknown (link)


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