harmalol
 
Notes:
None found
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CAS Number: 525-57-5Picture of molecule3D/inchi
FDA UNII: 2NQN80556Q
Nikkaji Web: J22.052C
XlogP3-AA: 0.60 (est)
Molecular Weight: 170.23464000
Formula: C12 H12 N 2O
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 177.8 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for harmalol usage levels up to:
 not for fragrance use.
 
Recommendation for harmalol flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5353656
National Institute of Allergy and Infectious Diseases: Data
 1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-7-one
Chemidplus: 0000525575
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References:
 1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-7-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5353656
Pubchem (cas): 525-57-5
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Metabolomics Database: Search
KEGG (GenomeNet): C06537
HMDB (The Human Metabolome Database): HMDB29838
FooDB: FDB001053
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 hippophae rhamnoides shoot
Search Trop  Picture
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Synonyms:
4,9-dihydro-1-methyl-3H-pyrido(3,4-b)indol-7-ol
1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-7-one
3H-pyrido(3,4-b)indol-7-ol, 4,9-dihydro-1-methyl- (8CI)(9CI)
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Articles:
PubMed: Therapeutic role of harmalol targeting nucleic acids: Biophysical perspective and in vitro cytotoxicity.
PubMed: Indole Alkaloids from Plants as Potential Leads for Antidepressant Drugs: A Mini Review.
PubMed: Determination of Tryptamines and β-Carbolines in Ayahuasca Beverage Consumed During Brazilian Religious Ceremonies.
PubMed: Parts-per-trillion detection of harmala alkaloids in Undaria pinnatifida algae by on-line solid phase extraction capillary electrophoresis mass spectrometry.
PubMed: Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea.
PubMed: DNA binding and apoptotic induction ability of harmalol in HepG2: Biophysical and biochemical approaches.
PubMed: Quality criterion to optimize separations in capillary electrophoresis: Application to the analysis of harmala alkaloids.
PubMed: A rapid and simple method for the determination of psychoactive alkaloids by CE-UV: application to Peganum Harmala seed infusions.
PubMed: The Potential of β Carbolin Alkaloids to Hinder Growth and Reverse Chloroquine Resistance in Plasmodium falciparum.
PubMed: Targeting different RNA motifs by beta carboline alkaloid, harmalol: a comparative photophysical, calorimetric, and molecular docking approach.
PubMed: Corrigendum to "Binding of alkaloid harmalol to DNA: Photophysical and calorimetric approach" [J. Photochem. Photobiol. B: Biol. 130 (2014) 272-280].
PubMed: Fast determination of harmala alkaloids in edible algae by capillary electrophoresis mass spectrometry.
PubMed: Sequence specific binding of beta carboline alkaloid harmalol with deoxyribonucleotides: binding heterogeneity, conformational, thermodynamic and cytotoxic aspects.
PubMed: Comment on "Binding of alkaloid harmalol to DNA: photophysical and calorimetric approach".
PubMed: Inhibition of myeloperoxidase activity by the alkaloids of Peganum harmala L. (Zygophyllaceae).
PubMed: Inhibition of monoamine oxidase (MAO) by β-carbolines and their interactions in live neuronal (PC12) and liver (HuH-7 and MH1C1) cells.
PubMed: Binding of alkaloid harmalol to DNA: photophysical and calorimetric approach.
PubMed: Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids.
PubMed: Simultaneous determination of harmine, harmaline and their metabolites harmol and harmalol in beagle dog plasma by UPLC-ESI-MS/MS and its application to a pharmacokinetic study.
PubMed: Recent pharmacological developments in β-carboline alkaloid "harmaline".
PubMed: Simultaneous determination of alkaloids and flavonoids from aerial parts of Passiflora species and dietary supplements using UPLC-UV-MS and HPTLC.
PubMed: Harmine is a potent antimalarial targeting Hsp90 and synergizes with chloroquine and artemisinin.
PubMed: Combined fluorescence spectroscopy and molecular modeling studies on the interaction between harmalol and human serum albumin.
PubMed: Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca.
PubMed: Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms.
PubMed: The inhibition activity of selected beta-carboline alkaloids on enzymes of acetylcholinesterase and butyrylcholinesterase.
PubMed: Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by β-carboline alkaloids, harmine derivatives.
PubMed: Beta-carboline alkaloids harmaline and harmalol induce melanogenesis through p38 mitogen-activated protein kinase in B16F10 mouse melanoma cells.
PubMed: Interaction of β-carboline alkaloids with RNA.
PubMed: Beta-carboline alkaloids bind DNA.
PubMed: Inhibitory effect of hydroxyindoles and their analogues on human melanoma tyrosinase.
PubMed: beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO).
PubMed: Harmol induces apoptosis by caspase-8 activation independently of Fas/Fas ligand interaction in human lung carcinoma H596 cells.
PubMed: Floral nectar composition of Peganum harmala L.
PubMed: Antiplatelet activity of beta-carboline alkaloids from Perganum harmala: a possible mechanism through inhibiting PLCgamma2 phosphorylation.
PubMed: Effect of Peganum harmala or its beta-carboline alkaloids on certain antibiotic resistant strains of bacteria and protozoa from poultry.
PubMed: Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts.
PubMed: Antioxidant properties of beta-carboline alkaloids are related to their antimutagenic and antigenotoxic activities.
PubMed: 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.
PubMed: Preparation, structure and spasmolytic activities of some derivatives of harmine series of alkaloids.
PubMed: High-affinity binding of beta-carbolines to imidazoline I2B receptors and MAO-A in rat tissues: norharman blocks the effect of morphine withdrawal on DOPA/noradrenaline synthesis in the brain.
PubMed: Comparison of the Protective Effect of Indole beta-carbolines and R-(-)-deprenyl Against Nitrogen Species-Induced Cell Death in Experimental Culture Model of Parkinson's Disease.
PubMed: Protective effect of 1-methylated beta-carbolines against 3-morpholinosydnonimine-induced mitochondrial damage and cell viability loss in PC12 cells.
PubMed: Microbial metabolites of harman alkaloids.
PubMed: N-methylated beta-carbolines protect PC12 cells from cytotoxic effect of MPP+ by attenuation of mitochondrial membrane permeability change.
PubMed: HPLC method for the analysis of harmol, harmalol, harmine and harmaline in the seeds of Peganum harmala L.
PubMed: Determination of N,N-dimethyltryptamine and beta-carboline alkaloids in human plasma following oral administration of Ayahuasca.
PubMed: 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.
PubMed: Comparative study on the vasorelaxant effects of three harmala alkaloids in vitro.
PubMed: Protective effect of harmalol and harmaline on MPTP neurotoxicity in the mouse and dopamine-induced damage of brain mitochondria and PC12 cells.
PubMed: Effects of some beta-carboline alkaloids on intact Trypanosoma cruzi epimastigotes.
PubMed: The effects of beta-carbolines in rats trained with ibogaine as a discriminative stimulus.
PubMed: beta-Carboline alkaloids as matrices for UV-matrix-assisted laser desorption/ionization time-of-flight mass spectrometry in positive and negative ion modes. Analysis of proteins of high molecular mass, and of cyclic and acyclic oligosaccharides.
PubMed: Genotoxic effects of structurally related beta-carboline alkaloids.
PubMed: Behavioural effects of Passiflora incarnata L. and its indole alkaloid and flavonoid derivatives and maltol in the mouse.
PubMed: Simple beta-carboline alkaloids as nucleic acids fluorochromes.
PubMed: [Radioprotective effect of gamma-harmine and its carboline analogues].
PubMed: Inhibition of platelet aggregation and arachidonic acid metabolism by B-carboline alkaloids.
PubMed: The cation receptor subsite of the choline transporter in preimplantation mouse conceptuses resembles a cation receptor subsite of several amino acid transporters.
PubMed: Effect of harmalol on blood pressure in anaesthetized rats.
PubMed: Antioxidative properties of harmane and beta-carboline alkaloids.
PubMed: Fluorescence of harmol, harmalol and 2-hydroxycarbazole in concentrated hydroxide solutions.
PubMed: Synthesis and characterization of novel biologically active platinum(II) and palladium(II) complexes of some beta-carboline alkaloids.
PubMed: Inhibition of calcium channels by harmaline and other harmala alkaloids in vascular and intestinal smooth muscles.
PubMed: Mutagenicities of nitrosated carboline derivatives.
PubMed: Interaction of carbolines and some GABA receptor ligands with the GABA and the benzodiazepine receptors.
PubMed: Food-borne amines and amides as potential precursors of endogenous carcinogens.
PubMed: Effects of betacarbolines on the automaticity of the guinea pig sinus node.
PubMed: Ionization processes of some harmala alkaloids.
PubMed: Rat brain aryl acylamidase: further characterization of multiple forms.
PubMed: Competitive inhibition of sodium-dependent high affinity choline uptake by harmala alkaloids.
PubMed: The effect of harmaline and related harmala alkaloids on ouabain-stimulated contractions of the guinea-pig ileum.
PubMed: The effect of harmaline and related beta-carbolines on the acetylcholine-stimulated contractions of guinea-pig ileum.
PubMed: Affinity of beta-carbolines on rat brain benzodiazepine and opiate binding sites.
PubMed: Cardiovascular actions of three harmala alkaloids: harmine, harmaline, and harmalol.
PubMed: The inhibitory effect of reserpine on the active sodium transport across the frog bladder.
PubMed: UDP glucuronyltransferase and phenolsulfotransferase in vivo and in vitro. Conjugation of harmol and harmalol.
PubMed: Glucuronidation of 3-O-methylnoradrenaline, harmalol and some related compounds.
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