This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Psilocybin
DrugBank Accession Number
DB11664
Background

Psilocybin has been investigated for the treatment of Anxiety and Stage IV Melanoma. In November, 2019, it was granted Breakthrough Therapy status by the FDA.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 284.2481
Monoisotopic: 284.092593554
Chemical Formula
C12H17N2O4P
Synonyms
  • Psilocibina
  • Psilocybin
  • Psilocybine
  • Psilocybinum
External IDs
  • CY 39
  • CY-39
  • DEA No. 7437

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Psilocybin is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Psilocybin.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Psilocybin.
AclidiniumPsilocybin may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Psilocybin.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Psilocybin.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Psilocybin.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Psilocybin.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Psilocybin.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Psilocybin.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Tryptamines and derivatives
Alternative Parents
Aryl phosphomonoesters / 3-alkylindoles / Alkaloids and derivatives / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
3-alkylindole / Alkaloid or derivatives / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl phosphate / Aryl phosphomonoester / Azacycle / Benzenoid / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, organic phosphate, tryptamine alkaloid (CHEBI:8614) / Alkaloids (C07576)
Affected organisms
Not Available

Chemical Identifiers

UNII
2RV7212BP0
CAS number
520-52-5
InChI Key
QVDSEJDULKLHCG-UHFFFAOYSA-N
InChI
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)
IUPAC Name
({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid
SMILES
CN(C)CCC1=CNC2=C1C(OP(O)(O)=O)=CC=C2

References

General References
Not Available
KEGG Compound
C07576
PubChem Compound
10624
PubChem Substance
347828033
ChemSpider
10178
BindingDB
50171269
ChEBI
8614
ChEMBL
CHEMBL194378
ZINC
ZINC000001530830
Wikipedia
Psilocybin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Active Not RecruitingTreatmentAlcohol Dependency1
2Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)2
2Active Not RecruitingTreatmentMajor depressive disorder, recurrent episode2
2CompletedSupportive CareAnxiety / Depressive Symptomatology / Malignancies1
2CompletedTreatmentMajor Depressive Disorder (MDD)1
2Not Yet RecruitingBasic ScienceSevere Depression1
2Not Yet RecruitingOtherBipolar Disorder, Type II1
2Not Yet RecruitingTreatmentAlcohol Use Disorders (AUD)1
2Not Yet RecruitingTreatmentCancer-related Problem/Condition / Demoralization / Hospices / Psilocybin / Psychotherapy / Terminal Cancer / Terminal Illness1
2Not Yet RecruitingTreatmentFibromyalgia, Primary1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.7 mg/mLALOGPS
logP1.25ALOGPS
logP-0.14ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area85.79 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.3 m3·mol-1ChemAxon
Polarizability27.73 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9010000000-fa35ae02266e8c5497f9
Mass Spectrum (Electron Ionization)MSsplash10-0pb9-9730000000-39c515eadd7ade5cb21a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at October 20, 2016 20:38 / Updated at June 12, 2020 16:53