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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:52:26 UTC
Update Date2019-07-23 06:35:21 UTC
HMDB IDHMDB0042000
Secondary Accession Numbers
  • HMDB42000
Metabolite Identification
Common NamePsilocin
DescriptionPsilocin (4-OH-DMT), an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective, but resemble those caused by LSD and mescaline. The effects typically last anywhere from three to eight hours depending on certain variables (such as metabolism, food interaction); however the effects can seem to last much longer due to psilocin's ability to distort the perception of time. Sulfur analogs are known with a benzothienyl replacement as well as 4-SH-DMT. N1-methylpsilocin is a functionally 5-HT2C receptor preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylized analog of psilocin, also known as 4-AcO-DMT. Additionally, substitution of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT (4-Hydroxy-N-Methyl-N-Isopropyltryptamine) and 4-HO-MET (4-Hydroxy-N-Methyl-N-Ethyltryptamine), respectively.
Structure
Data?1563863721
Synonyms
ValueSource
3-(2-(dimethylamino)Ethyl)indol-4-olChEBI
4-Hydroxy-N,N-dimethyltryptamineChEBI
4-OH-DMTChEBI
N,N-Dimethyl-4-hydroxytryptamineChEBI
PsilocineChEBI
PsilotsinChEBI
3-[2-(dimethylamino)Ethyl]-1H-indol-4-olHMDB
3-[2-(dimethylamino)Ethyl]-indol-4-olHMDB
Psilocin tartrate (1:1)MeSH
Psilocin hydrochlorideMeSH
(3-(2-dimethylamino)Ethyl)indol-4-olMeSH
Chemical FormulaC12H16N2O
Average Molecular Weight204.2682
Monoisotopic Molecular Weight204.126263144
IUPAC Name3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
Traditional Namepsilocin
CAS Registry Number520-53-6
SMILES
CN(C)CCC1=CNC2=C1C(O)=CC=C2
InChI Identifier
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
InChI KeySPCIYGNTAMCTRO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Alkaloid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point174.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.08 g/LALOGPS
logP1.98ALOGPS
logP1.15ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)8.97ChemAxon
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area39.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.42 m³·mol⁻¹ChemAxon
Polarizability23.11 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-62ea72268c3ac8349f99JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-62ea72268c3ac8349f99JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-4cca4e47c3bcf0ef37fcJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9030000000-8686b03317e1e073c475JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-30b1cea064c20727c677JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-0940000000-3d03cc820b34ad7de95cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qa-2900000000-6a888d817b451f311e43JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-b5141a6d394f0df7c3eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1290000000-19a265b5ec7903ebc866JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5900000000-47f31324e343d436c5c1JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9110000000-58fd69735c607f0dbac4JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001427
Chemspider ID4807
KEGG Compound IDC08312
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPsilocin
METLIN IDNot Available
PubChem Compound4980
PDB IDNot Available
ChEBI ID8613
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available