Psilocybin

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

Identification

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Name
Psilocybin
Accession Number
DB11664
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
  • Psilocibina
  • Psilocybin
  • Psilocybine
  • Psilocybinum
External IDs
CY 39 / CY-39 / DEA No. 7437
Categories
UNII
2RV7212BP0
CAS number
520-52-5
Weight
Average: 284.2481
Monoisotopic: 284.092593554
Chemical Formula
C12H17N2O4P
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Psilocybin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Psilocybin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Psilocybin.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Psilocybin is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Psilocybin.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Psilocybin.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Psilocybin.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Psilocybin.
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.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

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

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentMalignancies1
0RecruitingBasic ScienceHealthy Volunteers1
0RecruitingTreatmentAlzheimer's Disease (AD) / Depression / Depressive Symptomatology / Mild Cognitive Impairment (MCI)1
1Active Not RecruitingTreatmentDepression / Distress / Grief1
1CompletedBasic ScienceCentral Nervous System Agents / Hallucinogens / Pharmacologic Actions / Psilocybin / Psychotropic Drugs / Therapeutic Uses1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedTreatmentAnxiety1
1CompletedTreatmentHealthy Volunteers1
1Not Yet RecruitingHealth Services ResearchOpioid Use Disorders1
1Not Yet RecruitingTreatmentMigraine1
1RecruitingBasic ScienceBasic Science1
1RecruitingBasic ScienceHealthy Volunteers1
1RecruitingHealth Services ResearchReligious or Spiritual Problem / The Effects of Psilocybin-Facilitated Experience on the Psychology and Effectiveness of Professional Leaders in Religion1
1RecruitingTreatmentAnorexia Nervosa (AN)1
1RecruitingTreatmentCluster Headache1
1RecruitingTreatmentMajor Depressive Disorder (MDD)1
1RecruitingTreatmentMigraine1
1RecruitingTreatmentObsessive Compulsive Disorder (OCD)2
1RecruitingTreatmentPost-Traumatic Headaches1
1, 2CompletedBasic ScienceHealthy Volunteers1
2Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
2CompletedSupportive CareAnxiety / Depressive Symptomatology / Malignancies1
2Not Yet RecruitingBasic ScienceSevere Depression1
2Not Yet RecruitingTreatmentAlcohol Use Disorder (AUD)1
2RecruitingTreatmentAlcohol Dependence1
2RecruitingTreatmentCocaine-Related Disorders1
2RecruitingTreatmentMajor Depressive Disorder (MDD)3
2RecruitingTreatmentTreatment Resistant Depression (TRD)1
2Unknown StatusTreatmentAlcohol Dependence1
2WithdrawnTreatmentAnxiety / Stage IV Melanoma1
Not AvailableActive Not RecruitingBasic ScienceHealthy Volunteers1
Not AvailableRecruitingTreatmentNicotine Dependence1

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

Taxonomy

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
Tryptamine / Aryl phosphate / Aryl phosphomonoester / 3-alkylindole / Indole / Alkaloid or derivatives / Aralkylamine / Organic phosphoric acid derivative / Phosphoric acid ester / Substituted pyrrole
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, organic phosphate, tryptamine alkaloid (CHEBI:8614) / Alkaloids (C07576)

Drug created on October 20, 2016 14:38 / Updated on December 02, 2019 09:08