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Psilocybin information


Psilocybin
Kekulé, skeletal formula of canonical psilocybin
Spacefill model of canonical psilocybin
Names
Preferred IUPAC name
3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate
Identifiers
CAS Number
  • 520-52-5 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
273158
ChEBI
  • CHEBI:8614 checkY
ChEMBL
  • ChEMBL194378 checkY
ChemSpider
  • 10178 checkY
ECHA InfoCard 100.007.542 Edit this at Wikidata
EC Number
  • 208-294-4
KEGG
  • C07576 checkY
MeSH Psilocybine
PubChem CID
  • 10624
RTECS number
  • NM3150000
UNII
  • 2RV7212BP0 checkY
CompTox Dashboard (EPA)
  • DTXSID0048898 Edit this at Wikidata
InChI
  • 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
  • InChI=1/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)
SMILES
  • CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
Pharmacology
Dependence liability
Low
Routes of
administration
Oral, intravenous
Pharmacokinetics:
Metabolism
Hepatic
Biological half-life
Oral: 163±64 min
Intravenous: 74.1±19.6 min[1]
Excretion
Renal
Legal status
  • AU: S9/S8 (Controlled Drug)
  • BR: Class F2 (Prohibited psychotropics)[2]
  • CA: Schedule III
  • UK: Class A
  • US: Schedule I
Properties
Chemical formula
C12H17N2O4P
Molar mass 284.252 g·mol−1
Melting point 220–228 °C (428–442 °F)[3]
Solubility in water
Soluble
Solubility Soluble in boiling methanol and water
slightly soluble in ethanol
insoluble in chloroform, benzene[4]
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)
285 mg/kg (mouse, i.v.)
280 mg/kg (rat, i.v.)
12.5 mg/kg (rabbit, i.v.)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Psilocybin[a] (/ˌsləˈsbɪn/ sy-lə-SY-bin, /ˌsɪl-/) is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. The most potent are members of genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from about a dozen other genera. 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 lysergic acid diethylamide (LSD), mescaline, and dimethyltryptamine (DMT). In general, the effects include euphoria, visual and mental hallucinations, changes in perception, distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

Imagery found on cave paintings and rock art of modern-day Spain and Algeria suggests that human use of psilocybin mushrooms predates recorded history.[6] In Mesoamerica, the mushrooms had long been consumed in spiritual and divinatory ceremonies before Spanish chroniclers first documented their use in the sixteenth century. In 1958, the Swiss chemist Albert Hofmann isolated psilocybin and psilocin from the mushroom Psilocybe mexicana. Hofmann's employer Sandoz marketed and sold pure psilocybin to physicians and clinicians worldwide for use in psychedelic therapy. Although the increasingly restrictive drug laws of the 1960s and the 1970s curbed scientific research into the effects of psilocybin and other hallucinogens, 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 the effects of psilocybin are variable, depending on species or cultivar of mushrooms, dosage, individual physiology, and set and setting, as was 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. The mind-altering effects of psilocybin typically last from two to six hours, although to individuals under the influence of psilocybin, the effects 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. ^ Cite error: The named reference Passie2002 was invoked but never defined (see the help page).
  2. ^ 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.
  3. ^ a b Merck Index, 11th Edition, 7942
  4. ^ "Psilocybine". PubChem, US National Library of Medicine. August 27, 2022. Retrieved August 29, 2022.
  5. ^ Cite error: The named reference Pubchem was invoked but never defined (see the help page).
  6. ^ "Plants of Mind and Spirit - Fungi". web.archive.org. 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)


Cite error: There are <ref group=lower-alpha> tags or {{efn}} templates on this page, but the references will not show without a {{reflist|group=lower-alpha}} template or {{notelist}} template (see the help page).

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or gold cap, is a species of psilocybin mushroom of moderate potency whose principal active compounds are psilocybin and psilocin. It belongs to the...

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along with his brother Dennis, developed a technique for cultivating psilocybin mushrooms using spores they brought to America from the Amazon. In 1976...

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Magic truffle

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Magic truffles are the sclerotia of psilocybin mushrooms that are not technically the same as "mushrooms". They are masses of mycelium that contain the...

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Psilocybe semilanceata

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the psychoactive compounds psilocybin, psilocin and baeocystin. It is both one of the most widely distributed psilocybin mushrooms in nature, and one...

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Psilocybe

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family Hymenogastraceae. Many species contain the psychedelic compounds psilocybin and psilocin. A 2002 study of the molecular phylogeny of the agarics indicated...

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The Harvard Psilocybin Project was a series of experiments aimed at exploring the effects of psilocybin intake on the human mind conducted by Timothy...

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most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances...

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sub-threshold doses (microdoses) of serotonergic psychedelic drugs like LSD and psilocybin to potentially enhance creativity, energy, emotional balance, problem-solving...

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Baeocystin

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zwitterionic alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, aeruginascin...

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Psychedelic therapy

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Psilocybe azurescens

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compounds are psilocybin and psilocin. It is among the most potent of the tryptamine-bearing mushrooms, containing up to 1.8% psilocybin, 0.5% psilocin...

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Norbaeocystin

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recovery that utilizes classic psychedelics, such as LSD, mescaline, Psilocybin mushrooms, and cannabis to aid in recovery from harmful and addictive...

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distributed psilocybin mushroom. According to American naturalist and mycologist David Arora, Panaeolus cinctulus is the most common psilocybin mushroom...

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Psilocybe cyanescens

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mushroom. The main compounds responsible for its psychedelic effects are psilocybin and psilocin. It belongs to the family Hymenogastraceae. A formal description...

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