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Psilocybin

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Also known as COMP-360COMP360CY 39CY-39CY39IndocybinPsilocibinaPsilocybineTeonanacatlSID144206451

Summary

Psilocybin (CHEMBL194378) is a phase-3 clinical-stage small-molecule prodrug targeting HTR2C; indicated across 29 conditions including major depressive disorder and depressive disorder.

At a glance

  • Status: Max clinical phase 3 (not approved)
  • Modality: Small molecule
  • Targets: 1 (HTR2C)
  • Indications: 29 conditions
  • Clinical trials: 228
  • Chemistry: 284.25 Da · C12H17N2O4P

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL194378
NamePsilocybin
TypeSmall molecule
Max phase3
FDA approvedno
PubChem CID10624
ChEBICHEBI:8614
Molecular formulaC12H17N2O4P
Molecular weight284.25
InChIKeyQVDSEJDULKLHCG-UHFFFAOYSA-N

SMILES: CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O

IUPAC name: [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate

ChEBI definition: 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”).

Pharmacological roles (ChEBI): hallucinogen, prodrug, serotonergic agonist.

Other ChEBI roles (chemical / environmental): fungal metabolite.

Also known as: COMP-360, COMP360, CY 39, CY-39, CY39, Indocybin, Psilocibina, Psilocybin, Psilocybine, Teonanacatl, PSILOCYBIN, SID144206451

Parent form; salt/anhydrous children: CHEMBL6068522

Patent coverage: 2,010 distinct patent families (7,671 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 7,541 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
HTR2C5-HT2C receptorAgonist7.130%P28335

Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: 5-hydroxytryptamine receptor 2B, 5-hydroxytryptamine receptor 1A, 5-hydroxytryptamine receptor 2A, 5-hydroxytryptamine receptor 2C.

Bioactivity

ChEMBL activities: 5 potent at pChembl ≥ 5 of 5 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
HTR2B7.13EC5074nMCHEMBL_ACT_1617907
HTR2B7.01Ki98.7nMCHEMBL_ACT_25554503
HTR2C6.3EC50506nMCHEMBL_ACT_1617908
HTR2A5.46EC503475nMCHEMBL_ACT_1617906
HTR1A5.32IC504785nMCHEMBL_ACT_29288982

Target pathways

Aggregated over 1 target gene(s): HTR2C.

Top Reactome pathways

8 total, by targets touching each:

PathwayTargetsGenes
Signal Transduction1HTR2C
Signaling by GPCR1HTR2C
Class A/1 (Rhodopsin-like receptors)1HTR2C
Amine ligand-binding receptors1HTR2C
GPCR downstream signalling1HTR2C
Serotonin receptors1HTR2C
G alpha (q) signalling events1HTR2C
GPCR ligand binding1HTR2C

Dominant GO biological processes

GO termTargets
behavioral fear response1
intracellular calcium ion homeostasis1
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger1
phospholipase C-activating G protein-coupled receptor signaling pathway1
phospholipase C-activating serotonin receptor signaling pathway1
serotonin receptor signaling pathway1
chemical synaptic transmission1
locomotory behavior1
feeding behavior1
positive regulation of phosphatidylinositol biosynthetic process1
obsolete cGMP-mediated signaling1
regulation of nervous system process1
regulation of appetite1
regulation of corticotropin-releasing hormone secretion1
positive regulation of fat cell differentiation1

Indications & clinical

Indications

29 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
major depressive disorder3MONDO:0002009MONDO:0002009
depressive disorder3MONDO:0002050MONDO:0002050
cocaine dependence2MONDO:0005186EFO:0002610
opiate dependence2MONDO:0005530EFO:0010702
post-traumatic stress disorder2MONDO:0005146EFO:0001358
nicotine dependence2MONDO:0008575EFO:0003768
fibromyalgia2MONDO:0005546EFO:0005687
alcohol abuse2MONDO:0002046MONDO:0007079
bipolar disorder2MONDO:0004985MONDO:0004985
neoplasm2MONDO:0005070MONDO:0004992
anorexia nervosa2MONDO:0005351MONDO:0005351
cannabis dependence2MONDO:0005689EFO:0007191
psychiatric disorder2MONDO:0002025MONDO:0002025
obsessive-compulsive disorder1MONDO:0008114EFO:0004242
anxiety1MONDO:0011918EFO:0005230
methamphetamine dependence1MONDO:0005419EFO:0004701
Lyme disease1MONDO:0019632EFO:0008510
migraine disorder1MONDO:0005277MONDO:0005277
injury1MONDO:0021178EFO:0000546
hematopoietic and lymphoid system neoplasm1MONDO:0002334MONDO:0044881

9 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 228.

Phase distribution

PhaseTrials
PHASE2106
PHASE166
EARLY_PHASE117
PHASE1/PHASE215
Not specified14
PHASE38
PHASE2/PHASE32

Top trials by phase / activity

NCTPhaseStatusTitle
NCT05398484PHASE2/PHASE3RECRUITINGPsilocybin Therapy in Advanced Cancer
NCT05624268PHASE3ACTIVE_NOT_RECRUITINGEfficacy, Safety, and Tolerability of COMP360 in Participants With TRD
NCT05711940PHASE3ACTIVE_NOT_RECRUITINGEfficacy, Safety, and Tolerability of Two Administrations of COMP360 in Participants With TRD
NCT06247839PHASE3RECRUITINGThe Effects of Psilocybin on Self-Focus and Self-Related Processing in Major Depressive Disorder
NCT06303739PHASE3ACTIVE_NOT_RECRUITINGPsilocybin-Assisted Therapy in Treatment-Resistant Depression
NCT06308653PHASE3ACTIVE_NOT_RECRUITINGPsilocybin for Major Depressive Disorder (MDD)
NCT06943573PHASE3NOT_YET_RECRUITINGPsilocybin-Assisted Therapy for Treatment-Resistant Depression in Bipolar II Disorder
NCT07063862PHASE3RECRUITINGPsilocybin Microdose for Psychological and Existential Distress in Palliative Care (PSYCHED-PAL-RCT)
NCT07226232PHASE3NOT_YET_RECRUITINGPsilocybin Intervention for Veterans Overcoming Treatment-Resistant Depression
NCT07570654PHASE2/PHASE3NOT_YET_RECRUITINGRedefine Study: A Study Evaluating the Efficacy, Safety, and Tolerability of COMP360 in Participants With Post-traumatic Stress Disorder
NCT04433858PHASE2ACTIVE_NOT_RECRUITINGAn Open Label Study of the Safety and Efficacy of Psilocybin in Participants With Treatment-Resistant Depression (P-TRD)
NCT04620759PHASE2ACTIVE_NOT_RECRUITINGPsilocybin Treatment of Major Depressive Disorder With Co-occurring Alcohol Use Disorder
NCT04718792PHASE2ACTIVE_NOT_RECRUITINGPsilocybin for Treatment of Alcohol Use Disorder: a Feasibility Study
NCT04754061PHASE1/PHASE2RECRUITINGPSilocybin for psYCHological and Existential Distress in PALliative Care (PSYCHED-PAL)
NCT04982796PHASE1/PHASE2ACTIVE_NOT_RECRUITINGPsilocybin-Enhanced Psychotherapy for Methamphetamine Use Disorder
NCT05065294PHASE2ACTIVE_NOT_RECRUITINGPsilocybin Therapy for Depression in Bipolar II Disorder
NCT05301608PHASE1/PHASE2RECRUITINGEffects of Psilocybin on Electrophysiology and the Dynamic Content of Thought
NCT05403086PHASE2RECRUITINGPragmatic Trial of Psilocybin Therapy in Palliative Care
NCT05421065PHASE2ACTIVE_NOT_RECRUITINGPsilocybin-Assisted vs Ketamine-Assisted Psychotherapy for Alcohol Use Disorder
NCT05452772PHASE2RECRUITING5-HT2A Agonist Psilocybin in the Treatment of Tobacco Use Disorder
NCT05554094PHASE2ACTIVE_NOT_RECRUITINGPsilocybin for the Treatment of Veterans With Post-Traumatic Stress Disorder
NCT05733546PHASE2ACTIVE_NOT_RECRUITINGA Phase II, Multicentre, Randomised, Double-blind, Controlled Study to Investigate the Safety, Tolerability, Pharmacokinetics, and Efficacy of COMP360 in Participants With Recurrent Major Depressive Disorder
NCT05947383PHASE2ACTIVE_NOT_RECRUITINGTwo Doses of Psilocybin for the Treatment of MDD in Adults With Cancer
NCT05995769PHASE2RECRUITINGPsilocybin-Assisted Psychotherapy for Alcohol Use Disorder
NCT06001749PHASE2RECRUITINGPsilocybin in Cancer Pain Study
NCT06041152PHASE2ACTIVE_NOT_RECRUITINGDoes Psilocybin Change Synaptic Density in Amnestic Mild Cognitive Impairment
NCT06067737PHASE2RECRUITINGOutpatient Buprenorphine Induction With Psilocybin for Opioid Use Disorder
NCT06072898PHASE2RECRUITINGA Randomized Neuroimaging Trial of Psilocybin in Depression
NCT06132178PHASE2RECRUITINGPsilocybin rTMS for Treatment Resistant Depression
NCT06200155PHASE2RECRUITINGPsilocybin-Assisted Psychotherapy in Patients With Advanced Cancer on Maintenance Therapy
NCT06233344PHASE2RECRUITINGMindfulness-assisted Psychedelic Therapy
NCT06349083PHASE2RECRUITINGNeurobehavioral Mechanisms of Psilocybin-assisted Treatment for AUD
NCT06378229PHASE2RECRUITINGPsilocybin for Hospitalized Patients with Treatment-resistant Depression
NCT06386003PHASE2NOT_YET_RECRUITINGPsilocybin-Assisted Cognitive Processing Therapy for Chronic PTSD
NCT06399263PHASE2RECRUITINGStudy of Psilocybin for Anorexia in Young Adults
NCT06405607PHASE2RECRUITINGPsilocybin or Ketamine for Alcohol Use Disorder: An Active Comparator Trial
NCT06416085PHASE2ACTIVE_NOT_RECRUITINGPsilocybin-assisted Existential, Attachment and RelationaL (PEARL) Therapy for Patients With Advanced Cancer
NCT06444243PHASE2NOT_YET_RECRUITINGPsilocybin-assisted Therapy for Alcohol Use Disorder
NCT06455293PHASE2RECRUITINGPsilocybin Therapy for Depression in Parkinson’s Disease
NCT06471959PHASE1/PHASE2RECRUITINGPsychedelic-assisted Group Program for First Responders

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

276 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DIHYDROERGOTAMINEChEMBL + PubChemPhase 4 (approved)HTR2C
PIMAVANSERINChEMBL + PubChemPhase 4 (approved)HTR2C
AGOMELATINEChEMBLPhase 4 (approved)HTR2C
ALOSETRONChEMBLPhase 4 (approved)HTR2C
AMINEPTINEChEMBLPhase 4 (approved)HTR2C
AMIODARONEChEMBLPhase 4 (approved)HTR2C
AMITRIPTYLINEChEMBLPhase 4 (approved)HTR2C
AMLODIPINEChEMBLPhase 4 (approved)HTR2C
AMOXAPINEChEMBLPhase 4 (approved)HTR2C
APOMORPHINEChEMBLPhase 4 (approved)HTR2C
ARIPIPRAZOLEChEMBLPhase 4 (approved)HTR2C
ASENAPINEChEMBLPhase 4 (approved)HTR2C
ASTEMIZOLEChEMBLPhase 4 (approved)HTR2C
ATOMOXETINEChEMBLPhase 4 (approved)HTR2C
ATRACURIUMChEMBLPhase 4 (approved)HTR2C
ATROPINEChEMBLPhase 4 (approved)HTR2C
AZATADINEChEMBLPhase 4 (approved)HTR2C
AZELASTINEChEMBLPhase 4 (approved)HTR2C
BENFLUOREXChEMBLPhase 4 (approved)HTR2C
BENPERIDOLChEMBLPhase 4 (approved)HTR2C
BENZQUINAMIDEChEMBLPhase 4 (approved)HTR2C
BENZTROPINEChEMBLPhase 4 (approved)HTR2C
BITHIONOLChEMBLPhase 4 (approved)HTR2C
BOSUTINIBChEMBLPhase 4 (approved)HTR2C
BREXPIPRAZOLEChEMBLPhase 4 (approved)HTR2C
BROMOCRIPTINEChEMBLPhase 4 (approved)HTR2C
BROMPHENIRAMINEChEMBLPhase 4 (approved)HTR2C
BUSPIRONEChEMBLPhase 4 (approved)HTR2C
BUTRIPTYLINEChEMBLPhase 4 (approved)HTR2C
CALCITRIOLChEMBLPhase 4 (approved)HTR2C
CANNABIDIOLChEMBLPhase 4 (approved)HTR2C
CAPSAICINChEMBLPhase 4 (approved)HTR2C
CARIPRAZINEChEMBLPhase 4 (approved)HTR2C
CARVEDILOLChEMBLPhase 4 (approved)HTR2C
CEFPODOXIMEChEMBLPhase 4 (approved)HTR2C
CHLOPHEDIANOLChEMBLPhase 4 (approved)HTR2C
CHLORHEXIDINEChEMBLPhase 4 (approved)HTR2C
CHLOROPROCAINEChEMBLPhase 4 (approved)HTR2C
CHLORPROMAZINEChEMBLPhase 4 (approved)HTR2C
CINACALCETChEMBLPhase 4 (approved)HTR2C
CISAPRIDEChEMBLPhase 4 (approved)HTR2C
CITALOPRAMChEMBLPhase 4 (approved)HTR2C
CLEMASTINEChEMBLPhase 4 (approved)HTR2C
CLOMIPRAMINEChEMBLPhase 4 (approved)HTR2C
CLONIDINEChEMBLPhase 4 (approved)HTR2C
CLOTRIMAZOLEChEMBLPhase 4 (approved)HTR2C
CLOZAPINEChEMBLPhase 4 (approved)HTR2C
CYCLIZINEChEMBLPhase 4 (approved)HTR2C
CYCLOBENZAPRINEChEMBLPhase 4 (approved)HTR2C
CYPROHEPTADINEChEMBLPhase 4 (approved)HTR2C
DAPIPRAZOLEChEMBLPhase 4 (approved)HTR2C
DASATINIBChEMBLPhase 4 (approved)HTR2C
DAUNORUBICINChEMBLPhase 4 (approved)HTR2C
DESIPRAMINEChEMBLPhase 4 (approved)HTR2C
DESLORATADINEChEMBLPhase 4 (approved)HTR2C
DEXCHLORPHENIRAMINEChEMBLPhase 4 (approved)HTR2C
DICYCLOMINEChEMBLPhase 4 (approved)HTR2C
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)HTR2C
DIMENHYDRINATEChEMBLPhase 4 (approved)HTR2C
DIPHENHYDRAMINEChEMBLPhase 4 (approved)HTR2C

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot