Harmine (original) (raw)

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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

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action

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

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

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

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 / Hydrocarbon derivatives show 1 more

Substituents

Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Beta-carboline / Ether / Harman / Heteroaromatic compound / Hydrocarbon derivative / Indole / Indole or derivatives / Methylpyridine / Organic nitrogen compound / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Pyridine / Pyridoindole / Pyrrole 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

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

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

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Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

State

Solid

Experimental Properties

Not Available

Predicted Properties

Predicted ADMET Features

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Mass Spec (NIST)

Not Available

Spectra

Chromatographic Properties

Collision Cross Sections (CCS)

Targets

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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

1. 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

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

1. 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]
2. 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 August 26, 2024 19:21