Harmine
Star3
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Harmine
- DrugBank Accession Number
- DB07919
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- 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 ADual specificity tyrosine-phosphorylation-regulated kinase 2 inhibitorHumans ADual specificity tyrosine-phosphorylation-regulated kinase 3 inhibitorHumans ADual specificity tyrosine-phosphorylation-regulated kinase 1A inhibitorHumans AAmine oxidase [flavin-containing] A inhibitorHumans - 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
- Alkaloids
- Antidepressive Agents
- Carbolines
- Central Nervous System Agents
- Central Nervous System Depressants
- Enzyme Inhibitors
- Hallucinogens
- Harmala Alkaloids
- Heterocyclic Compounds, Fused-Ring
- Indole Alkaloids
- Indoles
- Indolizidines
- Indolizines
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Monoamine Oxidase Inhibitors
- Psychotropic Drugs
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data1 Completed Other Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 1 Completed Treatment Diabetes Mellitus 1 somestatus stop reason just information to hide 1 Recruiting Basic Science Neuropharmacological Investigation of Ayahuasca Constituents DMT and Harmine 1 somestatus stop reason just information to hide 0 Completed Basic Science Cognitive Function, Social 1 / Emotions / Empathy / Mood 1 somestatus stop reason just information to hide 0 Completed Basic Science Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 156.0077013 predictedDarkChem Lite v0.1.0 [M-H]- 156.0857013 predictedDarkChem Lite v0.1.0 [M-H]- 156.0971013 predictedDarkChem Lite v0.1.0 [M-H]- 149.00494 predictedDeepCCS 1.0 (2019) [M+H]+ 156.7712013 predictedDarkChem Lite v0.1.0 [M+H]+ 151.3401941 predictedDarkChem Standard v0.1.0 [M+H]+ 156.9295013 predictedDarkChem Lite v0.1.0 [M+H]+ 151.40051 predictedDeepCCS 1.0 (2019) [M+Na]+ 156.2508013 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.2839013 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.3865013 predictedDarkChem Lite v0.1.0 [M+Na]+ 157.42055 predictedDeepCCS 1.0 (2019)
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
- Yes
- Actions
- Inhibitor
- General Function
- Serine/threonine-protein kinase involved in the regulation of the mitotic cell cycle, cell proliferation, apoptosis, organization of the cytoskeleton and neurite outgrowth. Functions in part via its role in ubiquitin-dependent proteasomal protein degradation. Functions downstream of ATM and phosphorylates p53/TP53 at 'Ser-46', and thereby contributes to the induction of apoptosis in response to DNA damage. Phosphorylates NFATC1, and thereby inhibits its accumulation in the nucleus and its transcription factor activity. Phosphorylates EIF2B5 at 'Ser-544', enabling its subsequent phosphorylation and inhibition by GSK3B. Likewise, phosphorylation of NFATC1, CRMP2/DPYSL2 and CRMP4/DPYSL3 promotes their subsequent phosphorylation by GSK3B. May play a general role in the priming of GSK3 substrates. Inactivates GYS1 by phosphorylation at 'Ser-641', and potentially also a second phosphorylation site, thus regulating glycogen synthesis. Mediates EDVP E3 ligase complex formation and is required for the phosphorylation and subsequent degradation of KATNA1. Phosphorylates TERT at 'Ser-457', promoting TERT ubiquitination by the EDVP complex. Phosphorylates SIAH2, and thereby increases its ubiquitin ligase activity. Promotes the proteasomal degradation of MYC and JUN, and thereby regulates progress through the mitotic cell cycle and cell proliferation. Promotes proteasomal degradation of GLI2 and GLI3, and thereby plays a role in smoothened and sonic hedgehog signaling. Plays a role in cytoskeleton organization and neurite outgrowth via its phosphorylation of DCX and DPYSL2. Phosphorylates CRMP2/DPYSL2, CRMP4/DPYSL3, DCX, EIF2B5, EIF4EBP1, GLI2, GLI3, GYS1, JUN, MDM2, MYC, NFATC1, p53/TP53, TAU/MAPT and KATNA1. Can phosphorylate histone H1, histone H3 and histone H2B (in vitro). Can phosphorylate CARHSP1 (in vitro)
- Specific Function
- ATP binding
- Gene Name
- DYRK2
- Uniprot ID
- Q92630
- Uniprot Name
- Dual specificity tyrosine-phosphorylation-regulated kinase 2
- Molecular Weight
- 66651.18 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dual-specificity protein kinase that promotes disassembly of several types of membraneless organelles during mitosis, such as stress granules, nuclear speckles and pericentriolar material (PubMed:29973724). Dual-specificity tyrosine-regulated kinases (DYRKs) autophosphorylate a critical tyrosine residue in their activation loop and phosphorylate their substrate on serine and threonine residues (PubMed:29634919, PubMed:9748265). Acts as a central dissolvase of membraneless organelles during the G2-to-M transition, after the nuclear-envelope breakdown: acts by mediating phosphorylation of multiple serine and threonine residues in unstructured domains of proteins, such as SRRM1 and PCM1 (PubMed:29973724). Does not mediate disassembly of all membraneless organelles: disassembly of P-body and nucleolus is not regulated by DYRK3 (PubMed:29973724). Dissolution of membraneless organelles at the onset of mitosis is also required to release mitotic regulators, such as ZNF207, from liquid-unmixed organelles where they are sequestered and keep them dissolved during mitosis (PubMed:29973724). Regulates mTORC1 by mediating the dissolution of stress granules: during stressful conditions, DYRK3 partitions from the cytosol to the stress granule, together with mTORC1 components, which prevents mTORC1 signaling (PubMed:23415227). When stress signals are gone, the kinase activity of DYRK3 is required for the dissolution of stress granule and mTORC1 relocation to the cytosol: acts by mediating the phosphorylation of the mTORC1 inhibitor AKT1S1, allowing full reactivation of mTORC1 signaling (PubMed:23415227). Also acts as a negative regulator of EPO-dependent erythropoiesis: may place an upper limit on red cell production during stress erythropoiesis (PubMed:10779429). Inhibits cell death due to cytokine withdrawal in hematopoietic progenitor cells (PubMed:10779429). Promotes cell survival upon genotoxic stress through phosphorylation of SIRT1: this in turn inhibits p53/TP53 activity and apoptosis (PubMed:20167603)
- Specific Function
- ATP binding
- Gene Name
- DYRK3
- Uniprot ID
- O43781
- Uniprot Name
- Dual specificity tyrosine-phosphorylation-regulated kinase 3
- Molecular Weight
- 65713.225 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dual-specificity kinase which possesses both serine/threonine and tyrosine kinase activities (PubMed:20981014, PubMed:21127067, PubMed:23665168, PubMed:30773093, PubMed:8769099). Exhibits a substrate preference for proline at position P+1 and arginine at position P-3 (PubMed:23665168). Plays an important role in double-strand breaks (DSBs) repair following DNA damage (PubMed:31024071). Mechanistically, phosphorylates RNF169 and increases its ability to block accumulation of TP53BP1 at the DSB sites thereby promoting homologous recombination repair (HRR) (PubMed:30773093). Also acts as a positive regulator of transcription by acting as a CTD kinase that mediates phosphorylation of the CTD (C-terminal domain) of the large subunit of RNA polymerase II (RNAP II) POLR2A (PubMed:25620562, PubMed:29849146). May play a role in a signaling pathway regulating nuclear functions of cell proliferation (PubMed:14500717). Modulates alternative splicing by phosphorylating the splice factor SRSF6 (By similarity). Has pro-survival function and negatively regulates the apoptotic process (By similarity). Promotes cell survival upon genotoxic stress through phosphorylation of SIRT1 (By similarity). This in turn inhibits p53/TP53 activity and apoptosis (By similarity). Phosphorylates SEPTIN4, SEPTIN5 and SF3B1 at 'Thr-434' (By similarity)
- Specific Function
- actin binding
- Gene Name
- DYRK1A
- Uniprot ID
- Q13627
- Uniprot Name
- Dual specificity tyrosine-phosphorylation-regulated kinase 1A
- Molecular Weight
- 85583.41 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
4. DetailsAmine oxidase [flavin-containing] A
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the oxidative deamination of primary and some secondary amine such as neurotransmitters, with concomitant reduction of oxygen to hydrogen peroxide and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:18391214, PubMed:20493079, PubMed:24169519, PubMed:8316221). Preferentially oxidizes serotonin (PubMed:20493079, PubMed:24169519). Also catalyzes the oxidative deamination of kynuramine to 3-(2-aminophenyl)-3-oxopropanal that can spontaneously condense to 4-hydroxyquinoline (By similarity)
- Specific Function
- aliphatic amine oxidase activity
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at September 15, 2010 21:27 / Updated at October 03, 2024 04:24