harmalol
Identification
| Name | harmalol |
| CAS Number | 525-57-5 |
| FDA UNII | 2NQN80556Q |
| Molecular Formula | C12 H12 N 2O |
| Molecular Weight | 170.23464000 |
| Nikkaji Number | J22.052C |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 177.8 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
No supplier data available
Potential Uses
Natural Occurrence
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)
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.