<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2498</id>
  <title>T3D2457</title>
  <common-name>Psilocybin</common-name>
  <description>Psilocybin (pronounced /ˌsaɪlɵˈsaɪbɪn/ SYE-lə-SYE-bin) (also known as psilocybine) is a hallucinogenic (entheogenic, psychedelic) indole of the tryptamine family, found in psilocybin mushrooms. It is present in hundreds of species of fungi, including those of the genus Psilocybe, such as Psilocybe cubensis and Psilocybe semilanceata, but also reportedly isolated from a dozen or so other genera. Psilocybin mushrooms are commonly called "sacred mushrooms," "magic mushrooms," or more simply "shrooms". Possession, and in some cases usage, of psilocybin or psilocin has been outlawed in most countries across the globe. Proponents of its usage consider it to be an entheogen and a tool to supplement various types of practices for transcendence, including in meditation, psychonautics, and psychedelic psychotherapy. The intensity and duration of entheogenic effects of psilocybin mushrooms are highly variable, depending on species/cultivar of mushrooms, dosage, individual physiology, and set and setting. Though psilocybin rarely attracts much attention from mainstream media, when it does the focus tends to be on the recreational use, generally excluding any other uses of the drug. (L1143)</description>
  <cas>520-52-5</cas>
  <pubchem-id>10624</pubchem-id>
  <chemical-formula>C12H17N2O4P</chemical-formula>
  <weight>284.092590</weight>
  <appearance>White powder.</appearance>
  <melting-point>224°C</melting-point>
  <boiling-point>523.4°C</boiling-point>
  <density></density>
  <solubility></solubility>
  <specific-gravity></specific-gravity>
  <flash-point></flash-point>
  <vapour-pressure></vapour-pressure>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Psilocybin is rapidly dephosphorylated in the body to psilocin which then acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). Psilocin is an 5-HT1A and 5-HT2A/2C agonist. (L1143)</mechanism-of-toxicity>
  <metabolism>Psilocybin is rapidly dephosphorylated in the body to psilocin. Psilocybin is metabolized mostly in the liver where it becomes psilocin. It is broken down by the enzyme monoamine oxidase. (L1143)</metabolism>
  <toxicity>LD50: 280 mg/kg (Oral, Rat) (L1143)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Psilocybin has no recognized medical uses. However, it has been investigated as an experimental treatment for several disorders. (L1143)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Psilocybin is neurotoxic and produces hallucinations.  (L1143)</health-effects>
  <symptoms>Initially the subject may begin to feel somewhat disoriented, lethargic, and euphoric or sometimes depressed. At low doses, hallucinatory effects may occur, including enhancement of colors and the animation of geometric shapes. Closed-eye hallucination may occur, where the affected individual may see multi-coloured geometric shapes and vivid imaginative sequences. At higher doses, hallucinatory effects increase and experiences tend to be less social and more introspective or entheogenic. Open-eye visuals are more common, and may be very detailed although rarely confused with reality. (L1143)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-03T21:02:07Z</created-at>
  <updated-at type="dateTime">2026-05-14T19:11:23Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Psilocybin</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07576</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>8614</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>D011562</ctd-id>
  <stitch-id>Psilocybin</stitch-id>
  <drugbank-id>DB11664</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12</moldb-smiles>
  <moldb-formula>C12H17N2O4P</moldb-formula>
  <moldb-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)</moldb-inchi>
  <moldb-inchikey>QVDSEJDULKLHCG-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">284.2481</moldb-average-mass>
  <moldb-mono-mass type="decimal">284.092593554</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-0.14</logp>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL194378</chembl-id>
  <chemspider-id>10178</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002046</chemdb-id>
  <dsstox-id>DTXSID0048898</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00008179</susdat-id>
  <iupac>({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid</iupac>
  <moldb-polar-surface-area>85.78999999999999</moldb-polar-surface-area>
  <moldb-refractivity>73.29599999999999</moldb-refractivity>
  <moldb-polarizability>27.820584823426547</moldb-polarizability>
  <moldb-rotatable-bond-count>5</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>1.7443777657361865</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>9.536625544579383</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>1.25</moldb-alogps-logp>
  <moldb-alogps-logs>-2.02</moldb-alogps-logs>
  <moldb-alogps-solubility>2.70e+00 g/l</moldb-alogps-solubility>
</compound>
