Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H14N2O.ClH |
Molecular Weight | 250.724 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=CC2=C(C=C1)C3=C(N2)C(C)=NCC3
InChI
InChIKey=PULNGKOFHCQQQA-UHFFFAOYSA-N
InChI=1S/C13H14N2O.ClH/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13;/h3-4,7,15H,5-6H2,1-2H3;1H
Harmaline is a fluorescent psychoactive indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is a partially hydrogenated form of harmine. Harmaline is produced by various plants including Peganum harmala aswell as Banisteriopsis caapi. Harmaline has been investigated as an anti-cancer agent and for the treatment of dementia in rats. However, Harmaline is known to induce tremors in rats.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27356391
Curator's Comment: the referenced study was conducted in rat
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P50135 Gene ID: 3176.0 Gene Symbol: HNMT Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29243872 |
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Target ID: P04798 Gene ID: 1543.0 Gene Symbol: CYP1A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22037238 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
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Comparative study on the vasorelaxant effects of three harmala alkaloids in vitro. | 2001 Mar |
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Protective effect of harmaline and harmalol against dopamine- and 6-hydroxydopamine-induced oxidative damage of brain mitochondria and synaptosomes, and viability loss of PC12 cells. | 2001 May |
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Spasmolytic effects of three harmala alkaloids on guinea-pig isolated trachea. | 2001 Nov |
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Concurrent quantification of tremor and depression of locomotor activity induced in rats by harmaline and physostigmine. | 2001 Nov |
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Comparison of two intracranial self-stimulation (ICSS) paradigms in C57BL/6 mice: head-dipping and place-learning. | 2001 Nov 29 |
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Validation of a new computerized system for recording and analysing drug-induced tremor in rats. | 2001 Nov-Dec |
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Monoamine oxidase inhibition is unlikely to be relevant to the risks associated with phentermine and fenfluramine: a comparison with their abilities to evoke monoamine release. | 2001 Oct |
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Abnormal spontaneous and harmaline-stimulated Purkinje cell activity in the awake genetically dystonic rat. | 2002 Aug |
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Analysis of Cx36 knockout does not support tenet that olivary gap junctions are required for complex spike synchronization and normal motor performance. | 2002 Dec |
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Effects of rutin and harmaline on rat reflux oesophagitis. | 2002 Feb |
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An in vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. seeds extract and its beta-carboline alkaloids. | 2002 Jan-Apr |
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Characterization of the discriminable stimulus produced by 2-BFI: effects of imidazoline I(2)-site ligands, MAOIs, beta-carbolines, agmatine and ibogaine. | 2002 Mar |
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Stimulus-dependent activation of c-Fos in neurons and glia in the rat cerebellum. | 2002 Mar |
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Kinetics of binding of [(3)H]glycine to transport proteins in channel catfish brain. | 2002 Mar-Apr |
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Affinitive separation and on-line identification of antitumor components from Peganum nigellastrum by coupling a chromatographic column of target analogue imprinted polymer with mass spectrometry. | 2002 May 15 |
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Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism. | 2003 Jun |
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Citalopram, a selective serotonin reuptake inhibitor augments harmaline-induced tremor in rats. | 2004 Aug 12 |
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Enhanced inhibitory synaptic transmission in the cerebellar molecular layer of the GluRdelta2 knock-out mouse. | 2004 Dec 1 |
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Antinociceptive effects of Peganum harmala L. alkaloid extract on mouse formalin test. | 2004 Feb 19 |
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Toxicological evaluation of the staircase test for assessing fine motor movements. | 2004 Jan-Feb |
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Vagus nerve stimulation inhibits harmaline-induced tremor. | 2004 Jun 11 |
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In vitro activity of the beta-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum. | 2004 Mar-Apr |
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Can Zipf's law be adapted to normalize microarrays? | 2005 Feb 23 |
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MAPK activation in cerebellar basket cell terminals after harmaline treatment. | 2005 Jun |
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Short-term facilitation and depression in the cerebellum: some observations on wild-type and mutant rodents deficient in the extracellular matrix molecule tenascin C. | 2005 Jun |
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Fast and slow metabolizers of Hoasca. | 2005 Jun |
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Harmaline-induced tremor as a potential preclinical screening method for essential tremor medications. | 2005 Mar |
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Exacerbation of harmaline-induced tremor by imipramine. | 2005 May |
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Analysis of hallucinogenic constituents in Amanita mushrooms circulated in Japan. | 2006 Dec 20 |
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A species-specific difference in the effects of harmaline on the rodent olivocerebellar system. | 2006 Jan 12 |
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Phytochemical and pharmacological study of roots and leaves of Guiera senegalensis J.F. Gmel (Combretaceae). | 2006 Jun 30 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Rodent models of tremor. | 2007 |
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A possible mechanism for the beneficial effect of ethanol in essential tremor. | 2008 Jul |
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Loss of thalamic serotonin transporters in early drug-naïve Parkinson's disease patients is associated with tremor: an [(123)I]beta-CIT SPECT study. | 2008 May |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27356391
Curator's Comment: the referenced study was conducted in rat
Rats of vascular dementia were established with bilateral carotid artery ligation. After 30 days rats were treated nicergoline tablets 25, 12.5 and 6.25 mg/kg per day of total alkaloids of harmaline for 30 days. Learning and memory abilities were tested by Morris water maze, histomorphology in the hippocampal CA1 area was observed by HE staining, BAX and BCL-2 protein expression in the hippocampal CA1 area were detected by immunohistochemistry. 25 mg/kg of total alkaloids of harmaline shortened the incubation period in the third and fourth day significantly, and 12.5 mg/kg shortened the incubation period in the fourth day. Total alkaloids of harmaline improved the neurons pathological changes of the rats in the hippocampus CA1 area, 25 and 12.5 mg/kg of total alkaloids of harmaline downregulated the expression of apoptosis proteins BAX, upregulated the protein expression of BCL-2.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22037238
Human hepatoma HepG2 cells were maintained in Dulbecco's modified Eagle's medium, supplemented with 10% heat-inactivated fetal bovine serum, 2 mM L-glutamine, 100 IU/mL penicillin, and 100 micro-g/mL streptomycin and incubated at 37 deg-C under a 5% CO2 atmosphere. Cells were treated in serum-free medium with TCDD in presence of various concentrations of harmaline dissolved in up to 0.05% DMSO, and incubated for 24 hours. The effect of harmaline on HepG2 cell viability was determined by measuring the capacity of reducing enzymes present in viable cells to convert MTT to formazan crystals. At a concentration range of 0 25 micro-M, harmaline did not significantly affect cell viability when incubated with human hepatoma cells for 24 h either in presence or absence of TCDD.
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SUBSTANCE RECORD