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Chemical substance record

Psilocybin

520-52-5C12H17N2O4P284.252 g/mol
Organic/Inorganic Small MoleculeChEBI source record

A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional phosphoryloxy substituent at position 4. The major hallucinogenic alkaloid isolated from Psilocybe mushrooms (also known as Teonanácatl or "magic mushrooms"). — ChEBI

Safety references

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Identity & molecular properties

Source-linked values
CAS number520-52-5ChEBI ↗
Molecular formulaC12H17N2O4PChEBI ↗
Molar mass284.252 g/molChEBI ↗
Monoisotopic mass284.09259 DaChEBI ↗
Formal charge0ChEBI ↗
ChEBI identifierCHEBI:8614ChEBI ↗

Cross-source molecular data

PubChem
Molar mass284.25 g/molPubChem ↗
Exact mass284.09259403 DaPubChem ↗
Computed XLogP-1.6PubChem ↗
Topological polar surface area (Ų)85.8PubChem ↗
H-bond donors3PubChem ↗
H-bond acceptors5PubChem ↗
Rotatable bonds5PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

Copy any identifier
psilocybin
3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate
QVDSEJDULKLHCG-UHFFFAOYSA-N
CN(C)CCc1cnc2cccc(OP(=O)(O)O)c12
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)

Names & synonyms

3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphatepsilocibinapsilocybinepsilocybinum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology
organic phosphateChEBI parent class · 25703 ↗tryptamine alkaloidChEBI parent class · 48274 ↗tertiary amino compoundChEBI parent class · 50996 ↗
organophosphorus compoundorganic heterocyclic compoundorganic molecular entity

Roles recorded in ChEBI

geroprotectorantidepressantanxiolytic drugantipsychotic agentanalgesichallucinogenantineoplastic agentserotonergic agonistantibacterial drugprodrug

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass
Equivalent amount
0.00351801 mol

Uses 284.252 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions
C
Carbon · 12 atoms
50.71%
O
Oxygen · 4 atoms
22.51%
P
Phosphorus · 1 atom
10.90%
N
Nitrogen · 2 atoms
9.86%
H
Hydrogen · 17 atoms
6.03%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations
Experimental psychiatry. V. Psilocybine, a new psychotogenic drug. ↗The New England journal of medicine · 1960 Feb 11 · PMID 14437505
The pharmacology of psilocybin. ↗Addiction biology · 2002 Oct · PMID 14578010
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Sources & record history

Checked 27 Sep 2026
EMBL-EBI ChEBI · CHEBI:8614

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

NCBI PubChem · CID 10624 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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