Psilocybin

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
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

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Contraindications & Blackbox Warnings
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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
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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 CNS depression can be increased when Psilocybin is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Psilocybin.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Psilocybin.
AgomelatineThe risk or severity of CNS depression can be increased when Agomelatine is combined with Psilocybin.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with Psilocybin.
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
3Active Not RecruitingTreatmentBurnout, Professionals / Caregivers Burnout / Coronavirus Disease 2019 (COVID‑19) / Depression / Moral Injury / Post Traumatic Stress Disorder (PTSD)1
3Not Yet RecruitingTreatmentMajor Depressive Disorder (MDD)1
3RecruitingTreatmentMajor depressive disorder, recurrent episode2
2Active Not RecruitingHealth Services ResearchPost Traumatic Stress Disorder (PTSD) / Treatment Resistant Disorders1
2Active Not RecruitingTreatmentAlcohol Use Disorders (AUD)2

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/MSsplash10-000l-0090000000-4e24eaa265b584669127
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-5ba953b66515af3ad62c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-06rf-4690000000-e8a449d53d12f28bda12
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-ede313208748d6fc7ae5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-2900000000-010ce00d15e371f5e9a1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-2ad52befd1e6d7617b1e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.8312374
predicted
DarkChem Lite v0.1.0
[M-H]-173.0640374
predicted
DarkChem Lite v0.1.0
[M-H]-154.39867
predicted
DeepCCS 1.0 (2019)
[M+H]+175.4772374
predicted
DarkChem Lite v0.1.0
[M+H]+172.8758374
predicted
DarkChem Lite v0.1.0
[M+H]+156.75665
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.1422374
predicted
DarkChem Lite v0.1.0
[M+Na]+172.6265374
predicted
DarkChem Lite v0.1.0
[M+Na]+163.32037
predicted
DeepCCS 1.0 (2019)

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