Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H14N2O.ClH.2H2O |
Molecular Weight | 286.755 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.Cl.COC1=CC2=C(C=C1)C3=C(N2)C(C)=NCC3
InChI
InChIKey=LCEKUHFBUFUSSY-UHFFFAOYSA-N
InChI=1S/C13H14N2O.ClH.2H2O/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;2*1H2
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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Effects of stimulatory and depressant drugs on cyclic guanosine 3',5'-monophosphate and adenosine 3',5'-monophosphate levels in mouse brain. | 1976 |
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Stimulatory effect of harmane and other beta-carbolines on locus coeruleus neurons in anaesthetized rats. | 2001 Aug 10 |
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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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Effects of rutin and harmaline on rat reflux oesophagitis. | 2002 Feb |
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Comparative effects of dehydropirlindole and other compounds on rat brain monoamine oxidase type A. | 2002 Jan |
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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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A change in the pattern of activity affects the developmental regression of the Purkinje cell polyinnervation by climbing fibers in the rat cerebellum. | 2003 |
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Synthesis of some phenacyl derivatives of 1-methyl-7-methoxy-beta-carboline and their behavioural study. | 2003 Jan |
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Attenuation of activity-induced increases in cerebellar blood flow in mice lacking neuronal nitric oxide synthase. | 2003 Jul |
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Attenuation of activity-induced increases in cerebellar blood flow by lesion of the inferior olive. | 2003 Sep |
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Monoamine oxidase inhibitor poisoning resulting from Internet misinformation on illicit substances. | 2004 |
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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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Effect of diazepam on the CNS excitation and behavioural changes induced by harmaline and its newly synthesized analogues. | 2004 Jan |
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Allele-dependent changes of olivocerebellar circuit properties in the absence of the voltage-gated potassium channels Kv3.1 and Kv3.3. | 2004 Jun |
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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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Do naïve ruminants degrade alkaloids in the rumen? | 2005 Apr |
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Can Zipf's law be adapted to normalize microarrays? | 2005 Feb 23 |
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Modulation of voltage-gated channel currents by harmaline and harmane. | 2005 Jan |
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Antibacterial activity of 1-methyl-7-methoxy-beta-carboline and its phenacyl and coumarine analogues. | 2005 Jul |
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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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Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis. | 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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Beta-carboline and quinoline alkaloids in root cultures and intact plants of Peganum harmala. | 2005 May-Jun |
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A fatal intoxication following the ingestion of 5-methoxy-N,N-dimethyltryptamine in an ayahuasca preparation. | 2005 Nov-Dec |
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Simultaneous determination of nineteen hallucinogenic tryptamines/beta-calbolines and phenethylamines using gas chromatography-mass spectrometry and liquid chromatography-electrospray ionisation-mass spectrometry. | 2005 Oct 15 |
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Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs. | 2005 Sep-Oct |
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Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts. | 2006 Aug 11 |
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Protective effects of Peganum harmala L. extract, harmine and harmaline against human low-density lipoprotein oxidation. | 2006 Jul |
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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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Pharmacological characterization of cGMP regulation by the biarylpropylsulfonamide class of positive, allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors. | 2006 Oct |
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Effects of beta-carboline alkaloids on the object recognition task in mice. | 2006 Oct 26 |
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Rodent models of tremor. | 2007 |
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A quantitative synthesis of the medicinal ethnobotany of the Malinké of Mali and the Asháninka of Peru, with a new theoretical framework. | 2007 Dec 5 |
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A study on the antitumoral and differentiation effects of peganum harmala derivatives in combination with ATRA on leukaemic cells. | 2007 Jul |
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Determination of beta-carboline alkaloids in foods and beverages by high-performance liquid chromatography with electrochemical detection at a glassy carbon electrode modified with carbon nanotubes. | 2007 Mar 7 |
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Pontocerebellar hypoplasia type 2: a neuropathological update. | 2007 Oct |
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MPP(+)-induced cytotoxicity in neuroblastoma cells: Antagonism and reversal by guanosine. | 2007 Sep |
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Quantitative measurement of postural sway in mouse models of human neurodegenerative disease. | 2007 Sep 21 |
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Effects of zonisamide on experimental tremors in rats. | 2008 |
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Cytotoxicity of the beta-carboline alkaloids harmine and harmaline in human cell assays in vitro. | 2008 Aug |
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[Effect of harmaline on firing pattern of rat cerebellar Purkinje cells in ontogenesis]. | 2008 Jan-Feb |
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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