Tmic
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Record Information
Version2.0
Creation Date2009-07-03 21:03:18 UTC
Update Date2014-12-24 20:25:31 UTC
Accession NumberT3D2458
Identification
Common NamePsilocin
ClassSmall Molecule
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.
Compound Type
  • Amine
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
3-(2-(Dimethylamino)ethyl)indol-4-ol
3-[2-(Dimethylamino)ethyl]-1H-Indol-4-ol
3-[2-(Dimethylamino)ethyl]-Indol-4-ol
4-Hydroxy-N,N-dimethyltryptamine
N,N-Dimethyl-4-Hydroxytryptamine
Psilocine
Psilotsin
Chemical FormulaC12H16N2O
Average Molecular Mass204.268 g/mol
Monoisotopic Mass204.126 g/mol
CAS Registry Number520-53-6
IUPAC Name3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
Traditional Namepsilocin
SMILESCN(C)CCC1=CNC2=C1C(O)=CC=C2
InChI IdentifierInChI=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 KeyInChIKey=SPCIYGNTAMCTRO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives 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
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 Point174.5°C
Boiling PointNot Available
SolubilityNot Available
LogPNot 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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-62ea72268c3ac8349f99View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-62ea72268c3ac8349f99View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-4cca4e47c3bcf0ef37fcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9030000000-8686b03317e1e073c475View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-30b1cea064c20727c677View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-0940000000-3d03cc820b34ad7de95cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qa-2900000000-6a888d817b451f311e43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-b5141a6d394f0df7c3eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1290000000-19a265b5ec7903ebc866View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5900000000-47f31324e343d436c5c1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9110000000-58fd69735c607f0dbac4View in MoNA
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (1)
Mechanism of ToxicityPsilocin acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is an 5-HT1A and 5-HT2A/2C agonist. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPsilocin is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or psychedelic mushrooms. (2)
Minimum Risk LevelNot Available
Health EffectsPsilocin is neurotoxic and can cause hallucinations. (2)
SymptomsPsilocin may cause tachycardia, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals, synesthesia, increased body temperature, headache, sweating and chills, and nausea. (2)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB42000
PubChem Compound ID4980
ChEMBL IDCHEMBL65547
ChemSpider ID4807
KEGG IDC08312
UniProt IDNot Available
OMIM ID
ChEBI ID8613
BioCyc IDNot Available
CTD IDC009105
Stitch IDPsilocin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkPsilocin
References
Synthesis ReferenceNot Available
MSDST3D2458.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. Psilocin. Last Updated 22 July 2009. [Link]
  3. Wikipedia. Mushroom poisoning. Last Updated 10 August 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. Psilocin. Last Updated 22 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. Psilocin. Last Updated 22 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. Psilocin. Last Updated 22 July 2009. [Link]