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harmol

Supplier Sponsors

CAS Number: 487-03-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-645-9
FDA UNII: 7PQ075MCA6
Nikkaji Web:J102.018H
MDL:MFCD00834164
XlogP3:0.70 (est)
Molecular Weight:198.22490000
Formula:C12 H10 N2 O
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 8.781e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Carbosynth
For experimental / research use only.
Harmol
TCI AMERICA
For experimental / research use only.
Harmol >98.0%(T)
 
Safety Information:
Preferred SDS: View
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for harmol usage levels up to:
 not for fragrance use.
 
Recommendation for harmol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :68094
National Institute of Allergy and Infectious Diseases:Data
1-methyl-2,9-dihydropyrido[3,4-b]indol-7-one
Chemidplus:0000487036
 
References:
 1-methyl-2,9-dihydropyrido[3,4-b]indol-7-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):68094
Pubchem (cas):487-03-6
 
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
HMDB (The Human Metabolome Database):HMDB34217
FooDB:FDB012520
Export Tariff Code:2933.99.8290
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 hippophae rhamnoides leaf
Search Trop Picture
 
Synonyms:
1-methyl-2,9-dihydropyrido[3,4-b]indol-7-one
1-methyl-9H-pyrido(3,4-b)indol-7-ol
9H-pyrido(3,4-b)indol-7-ol, 1-methyl- (8CI)(9CI)
 

Articles:

PubMed:The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro.
PubMed:Harmine is an inflammatory inhibitor through the suppression of NF-κB signaling.
PubMed:UVA Photoactivation of Harmol Enhances Its Antifungal Activity against the PhytopathogensPenicillium digitatumandBotrytis cinerea.
PubMed:Indole Alkaloids from Plants as Potential Leads for Antidepressant Drugs: A Mini Review.
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:Antiviral activity of natural and synthetic β-carbolines against dengue virus.
PubMed:Quality criterion to optimize separations in capillary electrophoresis: Application to the analysis of harmala alkaloids.
PubMed:Interspecies metabolic diversity of harmaline and harmine in in vitro 11 mammalian liver microsomes.
PubMed:A rapid and simple method for the determination of psychoactive alkaloids by CE-UV: application to Peganum Harmala seed infusions.
PubMed:Functional Integrity of the Chimeric (Humanized) Mouse Liver: Enzyme Zonation, Physiologic Spaces, and Hepatic Enzymes and Transporters.
PubMed:The Potential of β Carbolin Alkaloids to Hinder Growth and Reverse Chloroquine Resistance in Plasmodium falciparum.
PubMed:Specific binding of [(18)F]fluoroethyl-harmol to monoamine oxidase A in rat brain cryostat sections, and compartmental analysis of binding in living brain.
PubMed:Interplay of metabolizing enzymes and transporter of xenobiotics.
PubMed:Determination of phytochemicals, antioxidant activity and total phenolic content in Andrographis paniculata using chromatographic methods.
PubMed:Fast determination of harmala alkaloids in edible algae by capillary electrophoresis mass spectrometry.
PubMed:Selective binding to monoamine oxidase A: in vitro and in vivo evaluation of (18)F-labeled β-carboline derivatives.
PubMed:Detection of monoamine oxidase a in brain of living rats with [18F]fluoroethyl-harmol PET.
PubMed:Inhibition of myeloperoxidase activity by the alkaloids of Peganum harmala L. (Zygophyllaceae).
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:Harmol induces autophagy and subsequent apoptosis in U251MG human glioma cells through the downregulation of survivin.
PubMed:Simultaneous determination of alkaloids and flavonoids from aerial parts of Passiflora species and dietary supplements using UPLC-UV-MS and HPTLC.
PubMed:Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca.
PubMed:Structure-activity relationship study of beta-carboline derivatives as haspin kinase inhibitors.
PubMed:Transcriptional and posttranslational inhibition of dioxin-mediated induction of CYP1A1 by harmine and harmol.
PubMed:The β-carboline alkaloid harmol induces cell death via autophagy but not apoptosis in human non-small cell lung cancer A549 cells.
PubMed:Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by β-carboline alkaloids, harmine derivatives.
PubMed:Mitochondrial dysfunction and biotransformation of β-carboline alkaloids, harmine and harmaline, on isolated rat hepatocytes.
PubMed:beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO).
PubMed:Banisteriopsis caapi, a unique combination of MAO inhibitory and antioxidative constituents for the activities relevant to neurodegenerative disorders and Parkinson's disease.
PubMed:Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC- bioautographic assay.
PubMed:Non-competitive androgen receptor inhibition in vitro and in vivo.
PubMed:Harmol induces apoptosis by caspase-8 activation independently of Fas/Fas ligand interaction in human lung carcinoma H596 cells.
PubMed:Antiplatelet activity of beta-carboline alkaloids from Perganum harmala: a possible mechanism through inhibiting PLCgamma2 phosphorylation.
PubMed:Apparent differences in mechanisms of harmol sulfate biliary excretion in mice and rats.
PubMed:Antioxidant properties of beta-carboline alkaloids are related to their antimutagenic and antigenotoxic activities.
PubMed:Effects of ayahuasca on psychometric measures of anxiety, panic-like and hopelessness in Santo Daime members.
PubMed:Evaluation of the role of multidrug resistance-associated protein (Mrp) 3 and Mrp4 in hepatic basolateral excretion of sulfate and glucuronide metabolites of acetaminophen, 4-methylumbelliferone, and harmol in Abcc3-/- and Abcc4-/- mice.
PubMed:The important role of Bcrp (Abcg2) in the biliary excretion of sulfate and glucuronide metabolites of acetaminophen, 4-methylumbelliferone, and harmol in mice.
PubMed:Effects of beta-carboline alkaloids on the object recognition task in mice.
PubMed:Effect of chlorine as substituent on the photochemistry and acid-base properties of beta-carboline alkaloids.
PubMed:Synthesis and antimycobacterial activity of some beta-carboline alkaloids.
PubMed:Sulfate conjugating and transport functions of MDCK distal tubular cells.
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:Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
PubMed:The modified dipeptide, enalapril, an angiotensin-converting enzyme inhibitor, is transported by the rat liver organic anion transport protein.
PubMed:Effects of molybdate on the sulfation of harmol and alpha-naphthol.
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:Effects of Ayahuasca on the human EEG.
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:Uptake of sulfate conjugates by isolated rat hepatocytes.
PubMed:Effect of erythrocyte binding on elimination of harmol by the isolated perfused rat liver.
PubMed:Simple beta-carboline alkaloids as nucleic acids fluorochromes.
PubMed:Methyl-beta-carbolinium analogs of MPP+ cause nigrostriatal toxicity after substantia nigra injections in rats.
PubMed:[Radioprotective effect of gamma-harmine and its carboline analogues].
PubMed:2,6-Dichloro-4-nitrophenol (DCNP), an alternate-substrate inhibitor of phenolsulfotransferase.
PubMed:Inhibition of platelet aggregation and arachidonic acid metabolism by B-carboline alkaloids.
PubMed:Fasting increases the sensitivity of hepatic harmol glucuronidation to hypoxia.
PubMed:Effects of microsomal enzyme inducers upon UDP-glucuronic acid concentration and UDP-glucuronosyltransferase activity in the rat intestine and liver.
PubMed:Extractionless determination of diclofenac sodium in serum using reversed-phase high-performance liquid chromatography with fluorimetric detection.
PubMed:Malaria infection impairs glucuronidation and biliary excretion by the isolated perfused rat liver.
PubMed:Expression of a high-affinity form of UDP-glucuronosyltransferase in human foetal liver cells in culture on exposure to mercuric chloride.
PubMed:Selective inhibition of glucuronidation by 2,2,2-triphenylethyl-UDP in isolated rat hepatocytes: conjugation of harmol, 3,3',5-triiodothyronine, and N-hydroxy-2-acetylaminofluorene.
PubMed:Antioxidative properties of harmane and beta-carboline alkaloids.
PubMed:Sulphation of the flavonoids quercetin and catechin by rat liver.
PubMed:Intestinal biotransformation of harmol and 1-naphthol in the rat. Further evidence of dose-dependent phase-II conjugation in situ.
PubMed:Mercury-induced UDP-glucuronyltransferase (UDPGT) activity in mouse kidney.
PubMed:Fluorescence of harmol, harmalol and 2-hydroxycarbazole in concentrated hydroxide solutions.
PubMed:Upper motor neurone effects in sheep of some beta-carboline alkaloids identified in zygophyllaceous plants.
PubMed:UDP-glucuronyltransferase activity toward harmol in human liver and human fetal liver cells in culture.
PubMed:Effect of glutathione depletion on sulfate activation and sulfate ester formation in rats.
PubMed:Measurement of beta-carbolines by high-performance liquid chromatography with fluorescence detection.
PubMed:Beta-carbolines as antagonists of the discriminative stimulus effects of diazepam in rats.
PubMed:Synergistic effects of hypoxia and fasting on harmol elimination in the isolated perfused rat liver.
PubMed:Hypoxia impairs conjugation and elimination of harmol in the isolated perfused rat liver.
PubMed:Metabolism of the beta-carbolines, harmine and harmol, by liver microsomes from phenobarbitone- or 3-methylcholanthrene-treated mice. Identification and quantitation of two novel harmine metabolites.
PubMed:Inhibition of calcium channels by harmaline and other harmala alkaloids in vascular and intestinal smooth muscles.
PubMed:Mutagenicities of nitrosated carboline derivatives.
PubMed:High-performance liquid chromatographic analysis of harmol and its conjugated metabolites after enzyme hydrolysis in biological fluids.
PubMed:Kinetics of sulfation in the rat in vivo and in the perfused rat liver.
PubMed:Heterogeneous distribution of the conjugation activity of acetaminophen and p-nitrophenol in isolated rat liver cells.
PubMed:Food-borne amines and amides as potential precursors of endogenous carcinogens.
PubMed:Alteration of transit time and direction of flow to probe the heterogeneous distribution of conjugating activities for harmol in the perfused rat liver preparation.
PubMed:Secretion of the organic anion harmol sulfate from liver into blood. Evidence for a carrier-mediated mechanism.
PubMed:Extrahepatic sulfation and glucuronidation in the rat in vivo. Determination of the hepatic extraction ratio of harmol and the extrahepatic contribution to harmol conjugation.
PubMed:Heterogeneous distribution of conjugation activities of harmol in isolated rat liver cells.
PubMed:D-cysteine as a selective precursor for inorganic sulfate in the rat in vivo. Effect of D-cysteine on the sulfation of harmol.
PubMed:Factors influencing sulfation in isolated rat hepatocytes.
PubMed:Effects of betacarbolines on the automaticity of the guinea pig sinus node.
PubMed:Comparison of beta-adrenoceptor antagonists as modulators of drug metabolism: effect of lipophilicity on microsomal phase I and II reactions.
PubMed:Metabolism of harmol and transport of harmol conjugates in isolated rat hepatocytes.
PubMed:Use of pentachlorophenol as long-term inhibitor of sulfation of phenols and hydroxamic acids in the rat in vivo.
PubMed:Ionization processes of some harmala alkaloids.
PubMed:Normal and retrograde perfusion to probe the zonal distribution of sulfation and glucuronidation activities of harmol in the perfused rat liver preparation.
PubMed:Differential effects of phenobarbitone and 3-methylcholanthrene induction on the hepatic microsomal metabolism of the beta-carbolines harmine and harmol.
PubMed:The dependence of the rate of sulphate conjugation on the plasma concentration of inorganic sulphate in the rat in vivo.
PubMed:Importance of extrahepatic sulphate conjugation.
PubMed:Kinetics of sulfation and glucuronidation of harmol in the perfused rat liver preparation. Disappearance of aberrances in glucuronidation kinetics by inhibition of sulfation.
PubMed:Cholestatic effect of harmol glucuronide in the rat. Prevention of harmol-induced cholestasis by increased formation of harmol sulfate.
PubMed:The effect of fasting on sulfation and glucuronidation in the rat in vivo.
PubMed:Selective inhibition of sulfate conjugation in the rat: pharmacokinetics and characterization of the inhibitory effect of 2,6-dichloro-4-nitrophenol.
PubMed:Elevation of conjugation capacity in isolated hepatocytes from BHA-treated mice.
PubMed:Sulphate and glucuronic acid conjugation of harmol in human fetal and adult liver tissue.
PubMed:Aberrant Pharmacokinetics of harmol in the perfused rat liver preparation: sulfate and glucuronide conjugations.
PubMed:Dose-dependent shifts in the sulfation and glucuronidation of phenolic compounds in the rat in vivo and in isolated hepatocytes. The role of saturation of phenolsulfotransferase.
PubMed:Effect of calcium ions on ethanol oxidation and drug glucuronidation in isolated hepatocytes.
PubMed:Inhibition of sulfation of phenols in vivo by 2,6-dichloro-4-nitrophenol: selectivity of its action in relation to other conjugations in the rat in vivo.
PubMed:Xenobiotic metabolism by isolated rat small intestinal cells.
PubMed:Assay of adenosine 3'-phosphate 5'-sulphatophosphate in hepatic tissues.
PubMed:Biliary and urinary excretion of drug conjugates: effect of diuresis and choleresis on excretion of harmol sulphate and harmol glucuronide in the rat.
PubMed:Metabolism of inorganic sulphate in the isolated perfused rat liver. Effect of sulphate concentration on the rate of sulphation by phenol sulphotransferase.
PubMed:Uptake of glucuronides into isolated hepatocytes and their effects on glucuronide and sulphate conjugation.
PubMed:The availability of inorganic sulphate in blood for sulphate conjugation of drugs in rat liver in vivo. (35S)Sulphate incorporation into harmol sulphate.
PubMed:Phenol sulphotransferase and uridine diphosphate glucuronyltransferase from rat liver in vivo and vitro. 2,6-Dichloro-4-nitrophenol as selective inhibitor of sulphation.
PubMed:Observations on the accessibility of acceptor substrates to the active centre of UDP-glucuronosyltransferase in vitro.
PubMed:Species and phenobarbitone-induced differences in the kinetic constants of liver microsomal harmine O-demethylation.
PubMed:UDP glucuronyltransferase and phenolsulfotransferase from rat liver in vivo and in vitro--IV. Species differences in harmol conjugation and elimination in bile and urine in vivo.
PubMed:UDP glucuronyltransferase and phenolsulfotransferase from rat liver in vivo and in vitro. III. The effect of phenolphthalein and its sulfate and glucuronide conjugate on conjugation and biliary excretion of harmol.
PubMed:UDP glucuronyltransferase and phenolsulfotransferase from rat liver in vivo and in vitro. Characterization of conjugation and biliary excretion of harmol in vivo and in the perfused liver.
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.
PubMed:[On 2 pharmacological properties, not yet known, of harmol].
 
Notes:
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