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Record Information
Version2.0
Creation Date2009-07-03 21:02:07 UTC
Update Date2014-12-24 20:25:31 UTC
Accession NumberT3D2457
Identification
Common NamePsilocybin
ClassSmall Molecule
DescriptionPsilocybin (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. (2)
Compound Type
  • Amine
  • Ester
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate ester
3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphate
3-2'-Dimethylaminoethylindol-4-phosphate
3-[2-(Dimethylamino)ethyl]indol-4-yl dihydrogen phosphate
4-Phosphoryloxy-N,N-dimethyltryptamine
4-Phosphoryloxy-omega-N,N-dimethyltryptamine
Constituent of "magic mushrooms"
Indocybin
Magic mushrooms
O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine
Psilocibin
Psilocibina
Psilocin phosphate ester
Psilocybine
Psilocybinum
Psilotsibin
Psylocybin
Teonanacatl
Chemical FormulaC12H17N2O4P
Average Molecular Mass284.248 g/mol
Monoisotopic Mass284.093 g/mol
CAS Registry Number520-52-5
IUPAC Name({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid
Traditional Namepsilocybin
SMILESCN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12
InChI IdentifierInChI=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)
InChI KeyInChIKey=QVDSEJDULKLHCG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • Aryl phosphate
  • Aryl phosphomonoester
  • 3-alkylindole
  • Indole
  • Alkaloid or derivatives
  • Aralkylamine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point224°C
Boiling Point523.4°C
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.7 mg/mLALOGPS
logP1.25ALOGPS
logP-0.14ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area85.79 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.3 m3·mol-1ChemAxon
Polarizability27.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-Bsplash10-0a4i-9010000000-fa35ae02266e8c5497f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2190000000-729379fc947ef47d59f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-1890000000-bb080562a0c4138738a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-3900000000-42b7586f3dc218478c89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-9030000000-4a785cb0926939dec3e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-90156cf6c239ddfc633cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-efd72851cd232625ef88View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0pb9-9730000000-39c515eadd7ade5cb21aView in MoNA
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (1)
Mechanism of ToxicityPsilocybin 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. (2)
MetabolismPsilocybin 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. (2)
Toxicity ValuesLD50: 280 mg/kg (Oral, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPsilocybin has no recognized medical uses. However, it has been investigated as an experimental treatment for several disorders. (2)
Minimum Risk LevelNot Available
Health EffectsPsilocybin is neurotoxic and produces hallucinations. (2)
SymptomsInitially 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. (2)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID10624
ChEMBL IDCHEMBL194378
ChemSpider ID10178
KEGG IDC07576
UniProt IDNot Available
OMIM ID
ChEBI ID8614
BioCyc IDNot Available
CTD IDD011562
Stitch IDPsilocybin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkPsilocybin
References
Synthesis ReferenceNot Available
MSDST3D2457.pdf
General References
  1. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  2. Wikipedia. Psilocybin. Last Updated 5 July 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli.
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular Weight:
46106.335 Da
References
  1. Wikipedia. Psilocybin. Last Updated 5 July 2009. [Link]
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
References
  1. Wikipedia. Psilocybin. Last Updated 5 July 2009. [Link]
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular Weight:
51820.705 Da
References
  1. Wikipedia. Psilocybin. Last Updated 5 July 2009. [Link]