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
Structure for Psilocybin (DB11664)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Psilocybin is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Psilocybin. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Psilocybin. Agomelatine The risk or severity of adverse effects can be increased when Agomelatine is combined with Psilocybin. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Psilocybin. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Psilocybin. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Psilocybin. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Psilocybin. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Psilocybin. Alverine The risk or severity of adverse effects can be increased when Alverine is combined with Psilocybin. 
Identify potential medication risksEasily 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
- External Links
- 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
Phase Status Purpose Conditions Count 3 Recruiting Treatment Major depressive disorder, recurrent episode 2 2 Active Not Recruiting Health Services Research Post Traumatic Stress Disorder (PTSD) / Treatment Resistant Disorders 1 2 Active Not Recruiting Treatment Alcohol Use Disorders (AUD) 1 2 Active Not Recruiting Treatment Binge Eating Disorder (BED) 1 2 Active Not Recruiting Treatment Depression / Major Depressive Disorder (MDD) 1 2 Active Not Recruiting Treatment Major Depressive Disorder (MDD) 2 2 Active Not Recruiting Treatment Major depressive disorder, recurrent episode 3 2 Completed Supportive Care Anxiety / Cancer / Depressive Symptomatology 1 2 Completed Treatment Alcohol Dependency 1 2 Completed Treatment Anorexia Nervosa (AN) 1
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
Property Value Source Water Solubility 2.7 mg/mL 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 27.73 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 - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - EI-B GC-MS splash10-0a4i-9010000000-fa35ae02266e8c5497f9 Mass Spectrum (Electron Ionization) MS splash10-0pb9-9730000000-39c515eadd7ade5cb21a Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at October 20, 2016 20:38 / Updated at June 12, 2020 16:53