Identification
- Generic Name
- Harmine
- DrugBank Accession Number
- DB07919
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Harmine (DB07919)
- Weight
- Average: 212.2472
Monoisotopic: 212.094963016 - Chemical Formula
- C13H12N2O
- Synonyms
- Banisterine
- Leucoharmine
- Telepathine
- Yageine
- Yajeine
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
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAmine oxidase [flavin-containing] A Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- 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. View sample adverse effects data in our new Data Library!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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as harmala alkaloids. These are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Harmala alkaloids
- Sub Class
- Not Available
- Direct Parent
- Harmala alkaloids
- Alternative Parents
- Beta carbolines / Indoles / Anisoles / Methylpyridines / Alkyl aryl ethers / Pyrroles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 1 more
- Substituents
- Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Beta-carboline / Ether / Harman / Heteroaromatic compound / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- harmala alkaloid (CHEBI:28121) / Indole alkaloids (C06538) / an alkaloid (CPD-9940)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4FHH5G48T7
- CAS number
- 442-51-3
- InChI Key
- BXNJHAXVSOCGBA-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
- IUPAC Name
- 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
- SMILES
- COC1=CC2=C(C=C1)C1=C(N2)C(C)=NC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0030311
- KEGG Compound
- C06538
- PubChem Compound
- 5280953
- PubChem Substance
- 99444390
- ChemSpider
- 4444445
- BindingDB
- 100152
- ChEBI
- 28121
- ChEMBL
- CHEMBL269538
- ZINC
- ZINC000018847046
- PDBe Ligand
- HRM
- Wikipedia
- Harmine
- PDB Entries
- 2z5x / 2z5y / 3anr / 5y86 / 7x9d
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Other Healthy Subjects (HS) 1 1 Completed Treatment Diabetes Mellitus 1 0 Completed Basic Science Cognitive Function 1, Social / Emotions / Empathy / Mood 1 0 Completed Basic Science Healthy Subjects (HS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0613 mg/mL ALOGPS logP 3.05 ALOGPS logP 1.85 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 13.54 Chemaxon pKa (Strongest Basic) 6.15 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.91 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 62.37 m3·mol-1 Chemaxon Polarizability 23.45 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.997 Blood Brain Barrier + 0.9854 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.5688 P-glycoprotein inhibitor I Non-inhibitor 0.7264 P-glycoprotein inhibitor II Non-inhibitor 0.8251 Renal organic cation transporter Non-inhibitor 0.6919 CYP450 2C9 substrate Non-substrate 0.8379 CYP450 2D6 substrate Non-substrate 0.6556 CYP450 3A4 substrate Non-substrate 0.5656 CYP450 1A2 substrate Inhibitor 0.9629 CYP450 2C9 inhibitor Non-inhibitor 0.9481 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.6929 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6307 Ames test AMES toxic 0.9162 Carcinogenicity Non-carcinogens 0.9682 Biodegradation Not ready biodegradable 0.9949 Rat acute toxicity 2.0878 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8598 hERG inhibition (predictor II) Non-inhibitor 0.7301
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serotonin binding
- Specific Function
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:27 / Updated at June 12, 2020 16:52