ContaminantDB: Psilocybin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-03 21:02:07 UTC

Update Date

2026-05-14 19:11:23 UTC

Accession Number

CHEM002046

Identification

Common Name

Psilocybin

Class

Small Molecule

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. (2)

Contaminant Sources

STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Ester
Fungal Toxin
Human Neurotoxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate ester	ChEBI
3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphate	ChEBI
4-Phosphoryloxy-N,N-dimethyltryptamine	ChEBI
Indocybin	ChEBI
O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine	ChEBI
Psilocibina	ChEBI
Psilocin phosphate ester	ChEBI
Psilocybine	ChEBI
Psilocybinum	ChEBI
3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphoric acid ester	Generator
3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphoric acid	Generator
Psilocin phosphoric acid ester	Generator
Psilocibin	MeSH

Chemical Formula

C₁₂H₁₇N₂O₄P

Average Molecular Mass

284.248 g/mol

Monoisotopic Mass

284.093 g/mol

CAS Registry Number

520-52-5

IUPAC Name

({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid

Traditional Name

psilocybin

SMILES

CN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12

InChI Identifier

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)

InChI Key

QVDSEJDULKLHCG-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:8614 )
organic phosphate (CHEBI:8614 )
tryptamine alkaloid (CHEBI:8614 )
Alkaloids (C07576 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	224°C
Boiling Point	523.4°C
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.7 g/L	ALOGPS
logP	1.25	ALOGPS
logP	-0.14	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.3 m³·mol⁻¹	ChemAxon
Polarizability	27.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9010000000-fa35ae02266e8c5497f9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9020000000-f7ffaae6f70e80e058d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2190000000-729379fc947ef47d59f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-1890000000-bb080562a0c4138738a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-3900000000-42b7586f3dc218478c89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-9030000000-4a785cb0926939dec3e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-90156cf6c239ddfc633c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-efd72851cd232625ef88	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0pb9-9730000000-39c515eadd7ade5cb21a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (1)

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. (2)

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. (2)

Toxicity Values

LD50: 280 mg/kg (Oral, Rat) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Psilocybin has no recognized medical uses. However, it has been investigated as an experimental treatment for several disorders. (2)

Minimum Risk Level

Not Available

Health Effects

Psilocybin is neurotoxic and produces hallucinations. (2)

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. (2)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB11664

HMDB ID

HMDB0256899

FooDB ID

Not Available

Phenol Explorer ID