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21655-84-5 | HARMAN HYDROCHLORIDE
CAS No: 21655-84-5 Catalog No: AG00BFIO MDL No:
Product Description
Catalog Number:
AG00BFIO
Chemical Name:
HARMAN HYDROCHLORIDE
CAS Number:
21655-84-5
Molecular Formula:
C12H11ClN2
Molecular Weight:
218.6821
IUPAC Name:
1-methyl-9H-pyrido[3,4-b]indole;hydrochloride
InChI:
InChI=1S/C12H10N2.ClH/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12;/h2-7,14H,1H3;1H
InChI Key:
COVNOIRYDKHLJD-UHFFFAOYSA-N
SMILES:
Cc1nccc2c1[nH]c1c2cccc1.Cl
EC Number:
244-507-7
UNII:
TC01Z184R9
Properties
Complexity:
216
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
218.061g/mol
Formal Charge:
0
Heavy Atom Count:
15
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
218.684g/mol
Monoisotopic Mass:
218.061g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
28.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. | Bioorganic & medicinal chemistry 20121115 |
| Structural insights into cholinesterases inhibition by harmane β-carbolinium derivatives: a kinetics-molecular modeling approach. | Phytochemistry 20120901 |
| Binding interaction and rotational-relaxation dynamics of a cancer cell photosensitizer with various micellar assemblies. | The journal of physical chemistry. B 20120816 |
| Involvement of the cholinergic system of CA1 on harmane-induced amnesia in the step-down passive avoidance test. | Journal of psychopharmacology (Oxford, England) 20120801 |
| Detection of bioactive exometabolites produced by the filamentous marine cyanobacterium Geitlerinema sp. | Marine biotechnology (New York, N.Y.) 20120801 |
| Blood harmane (1-methyl-9H-pyrido[3,4-b]indole) concentrations in essential tremor: repeat observation in cases and controls in New York. | Journal of toxicology and environmental health. Part A 20120615 |
| Differential interactions of a biological photosensitizer with liposome membranes having varying surface charges. | Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20120401 |
| The impact of dihydrogen phosphate anions on the excited-state proton transfer of harmane. Effect of β-cyclodextrin on these photoreactions. | The journal of physical chemistry. A 20120112 |
| Formation of heterocyclic amines during cooking of duck meat. | Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20120101 |
| Exploring the strength, mode, dynamics, and kinetics of binding interaction of a cationic biological photosensitizer with DNA: implication on dissociation of the drug-DNA complex via detergent sequestration. | The journal of physical chemistry. B 20111020 |
| Simiranes A and B: erythroxylanes diterpenes and other compounds from Simira eliezeriana (Rubiaceae). | Natural product research 20111001 |
| Modulation of prototropic activity and rotational relaxation dynamics of a cationic biological photosensitizer within the motionally constrained bio-environment of a protein. | The journal of physical chemistry. B 20110901 |
| Monoamine oxidase A binding in the prefrontal and anterior cingulate cortices during acute withdrawal from heavy cigarette smoking. | Archives of general psychiatry 20110801 |
| Dietary inhibitors of monoamine oxidase A. | Journal of neural transmission (Vienna, Austria : 1996) 20110701 |
| Effects of harmane and other β-carbolines on apomorphine-induced licking behavior in rat. | Pharmacology, biochemistry, and behavior 20110401 |
| Blood harmane, blood lead, and severity of hand tremor: evidence of additive effects. | Neurotoxicology 20110301 |
| Screening of non-polar heterocyclic amines in urine by microextraction in packed sorbent-fluorimetric detection and confirmation by capillary liquid chromatography. | Talanta 20110215 |
| Relationship between blood harmane and harmine concentrations in familial essential tremor, sporadic essential tremor and controls. | Neurotoxicology 20101201 |
| Interaction of β-carboline alkaloids with RNA. | DNA and cell biology 20101201 |
| Harman induces CYP1A1 enzyme through an aryl hydrocarbon receptor mechanism. | Toxicology and applied pharmacology 20101115 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Beta-carboline alkaloids bind DNA. | Journal of photochemistry and photobiology. B, Biology 20100802 |
| Involvement of dopamine D1/D2 receptors on harmane-induced amnesia in the step-down passive avoidance test. | European journal of pharmacology 20100525 |
| Electrophysiological characterization of harmane-induced activation of mesolimbic dopamine neurons. | European journal of pharmacology 20100310 |
| Electrospray MS-based characterization of beta-carbolines--mutagenic constituents of thermally processed meat. | Molecular nutrition & food research 20100301 |
| Molecular determinants of beta-carboline inhibition of the glycine receptor. | Journal of neurochemistry 20090901 |
| The effects of synthetic and endogenous imidazoline binding site ligands on neuronal activity in discrete brain regions of naive and restraint-stressed rats. | European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20090501 |
| The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, alpha-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane. | Journal of mass spectrometry : JMS 20090201 |
| Effect of Peganum harmala or its beta-carboline alkaloids on certain antibiotic resistant strains of bacteria and protozoa from poultry. | Phytotherapy research : PTR 20081101 |
| Oxidative metabolism of the bioactive and naturally occurring beta-carboline alkaloids, norharman and harman, by human cytochrome P450 enzymes. | Chemical research in toxicology 20081101 |
| Environmental epidemiology of essential tremor. | Neuroepidemiology 20081001 |
| Cancer and blood concentrations of the comutagen harmane in essential tremor. | Movement disorders : official journal of the Movement Disorder Society 20080915 |
| Quantification of heterocyclic aromatic amines in fried meat by HPTLC/UV-FLD and HPLC/UV-FLD: a comparison of two methods. | Journal of agricultural and food chemistry 20080625 |
| Effects of harman and norharman on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells. | European journal of pharmacology 20080610 |
| Influence of the presence of methyl cyclodextrins in high-performance liquid chromatography mobile phases on the separation of beta-carboline alkaloids. | Journal of chromatography. A 20080530 |
| Dietary epidemiology of essential tremor: meat consumption and meat cooking practices. | Neuroepidemiology 20080501 |
| Higher blood harmane (1-methyl-9H-pyrido[3,4-b]indole) concentrations correlate with lower olfactory scores in essential tremor. | Neurotoxicology 20080501 |
| Elevated blood harmane (1-methyl-9H-pyrido[3,4-b]indole) concentrations in essential tremor. | Neurotoxicology 20080301 |
| The endogenous alkaloid harmane: acidifying and activity-reducing effects on hippocampal neurons in vitro. | Progress in neuro-psychopharmacology & biological psychiatry 20080215 |
| Role of acetaldehyde in tobacco smoke addiction. | European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20071001 |
| Blood harmane is correlated with cerebellar metabolism in essential tremor: a pilot study. | Neurology 20070807 |
| Quantification of the neurotoxic beta-carboline harmane in barbecued/grilled meat samples and correlation with level of doneness. | Journal of toxicology and environmental health. Part A 20070601 |
| Factors influencing the norharman and harman contents in espresso coffee. | Journal of agricultural and food chemistry 20070307 |
| Structural characterization of native high-methoxylated pectin using nuclear magnetic resonance spectroscopy and ultraviolet matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Comparative use of 2,5-dihydroxybenzoic acid and nor-harmane as UV-MALDI matrices. | Rapid communications in mass spectrometry : RCM 20070101 |
| Comparative aromatic hydroxylation and N-demethylation of MPTP neurotoxin and its analogs, N-methylated beta-carboline and isoquinoline alkaloids, by human cytochrome P450 2D6. | Toxicology and applied pharmacology 20061101 |
| Efficacy of planar chromatography coupled to (tandem) mass spectrometry for employment in trace analysis. | Journal of chromatography. A 20060922 |
| Neurochemical mechanisms of the dorsal pallidum in the antiaversive effects of anxiolytics in various models of anxiety. | Neuroscience and behavioral physiology 20060901 |
| Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test. | European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20060701 |
| Phytochemical and pharmacological study of roots and leaves of Guiera senegalensis J.F. Gmel (Combretaceae). | Journal of ethnopharmacology 20060630 |
| In vitro and ex vivo distribution of [3H]harmane, an endogenous beta-carboline, in rat brain. | Neuropharmacology 20060301 |
| Autoradiographical distribution of imidazoline binding sites in monoamine oxidase A deficient mice. | Journal of neurochemistry 20060301 |
| Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. | Life sciences 20060118 |
| Centrally acting imidazolines stimulate vascular alpha 1A-adrenergic receptors in Rat-Tail Artery. | Cellular and molecular neurobiology 20060101 |
| Harmane inhibits serotonergic dorsal raphe neurons in the rat. | Psychopharmacology 20051101 |
| Investigation of the separation of heterocyclic aromatic amines by reversed phase ion-pair liquid chromatography coupled with tandem mass spectrometry: the role of ion pair reagents on LC-MS/MS sensitivity. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051025 |
| Blood harmane concentrations and dietary protein consumption in essential tremor. | Neurology 20050809 |
| Lack of combination hepatocarcinogenicity of harman, norharman and amitrole when given with NaNO2 in the rat. | The Journal of toxicological sciences 20050201 |
| Modulation of voltage-gated channel currents by harmaline and harmane. | British journal of pharmacology 20050101 |
| Matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry of beta-(1 --> 3), beta-(1 --> 4)-xylans from Nothogenia fastigiata using nor-harmane as matrix. | Rapid communications in mass spectrometry : RCM 20050101 |
| Fluorescence quenching of beta-carboline alkaloids in micellar media. A study to select the adequate surfactant to use in analytical techniques. | Luminescence : the journal of biological and chemical luminescence 20050101 |
| Comprehensive photochemistry and photophysics of land- and marine-based beta-carbolines employing time-resolved emission and flash transient spectroscopy. | Photochemistry and photobiology 20050101 |
| Harmane and harmalan are bioactive components of classical clonidine-displacing substance. | Biochemistry 20041228 |
| Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke. | Food additives and contaminants 20041101 |
| The putative imidazoline receptor agonist, harmane, promotes intracellular calcium mobilisation in pancreatic beta-cells. | European journal of pharmacology 20041006 |
| Modulation of cytochrome P450 1A1 by food-derived heterocyclic aromatic amines. | Toxicology 20040701 |
| Transport of harman alkaloids across Caco-2 cell monolayers. | Chemical & pharmaceutical bulletin 20040401 |
| Exposure to beta-carbolines norharman and harman. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040325 |
| In vitro activity of the beta-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum. | Experimental parasitology 20040101 |
| Effects of the beta-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans. | European journal of pharmacology 20031215 |
| Endogenous beta-carbolines as clonidine-displacing substances. | Annals of the New York Academy of Sciences 20031201 |
| Characterization of [(3)H]harmane binding to rat whole brain membranes. | Annals of the New York Academy of Sciences 20031201 |
| Effect of harmane on mononeuropathic pain in rats. | Annals of the New York Academy of Sciences 20031201 |
| Inhibitory effect of harmane on morphine-dependent Guinea pig ileum. | Annals of the New York Academy of Sciences 20031201 |
| Effect of harmane on the convulsive threshold in epilepsy models in mice. | Annals of the New York Academy of Sciences 20031201 |
| Harmane induces anxiolysis and antidepressant-like effects in rats. | Annals of the New York Academy of Sciences 20031201 |
| Endogenous imidazoline receptor ligands relax rat aorta by an endothelium-dependent mechanism. | Annals of the New York Academy of Sciences 20031201 |
| Atypical [(3)H]clonidine binding sites in human caudate and platelets on cryostat-cut sections. | Annals of the New York Academy of Sciences 20031201 |
| Effects of harman and harmine on naloxone-precipitated withdrawal syndrome in morphine-dependent rats. | Life sciences 20030919 |
| Microbial metabolites of harman alkaloids. | Chemical & pharmaceutical bulletin 20030601 |
| Agmatine and imidazoline systems--fourth international symposium: 9-11 April 2003, San Diego, CA, USA. | IDrugs : the investigational drugs journal 20030601 |
| Identification of harman as the antibiotic compound produced by a tunicate-associated bacterium. | Marine biotechnology (New York, N.Y.) 20030101 |
| Elevation of blood beta-carboline alkaloids in essential tremor. | Neurology 20021224 |
| Collision-induced dissociation actualized the H+-promoted reaction as observed in vitro; harman formation from beta-carboline-type monoterpenoid glucoindole alkaloids. | Chemical & pharmaceutical bulletin 20021101 |
| Identification and occurrence of the bioactive beta-carbolines norharman and harman in coffee brews. | Food additives and contaminants 20020801 |
| Tetrahydro-beta-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay. | Free radical research 20020801 |
| Natural variations of precursors in pig meat affect the yield of heterocyclic amines--effects of RN genotype, feeding regime, and sex. | Journal of agricultural and food chemistry 20020508 |
| The levels of norharman are high enough after smoking to affect monoamineoxidase B in platelets. | European journal of pharmacology 20020419 |
| Genotoxic and recombinogenic activities of the two beta-carboline alkaloids harman and harmine in Saccharomyces cerevisiae. | Mutation research 20020320 |
| Synergistic in vitro antimalarial activity of plant extracts used as traditional herbal remedies in Mali. | Parasitology research 20020201 |
| [Serum norharman and harman analysis using high pressure liquid chromatography/mass spectrometry and value of beta-carbolines as blood alcohol markers]. | Archiv fur Kriminologie 20020101 |
| Toxicokinetics of tremorogenic natural products, harmane and harmine, in male Sprague-Dawley rats. | Journal of toxicology and environmental health. Part A 20011221 |
| Degradation of tetrahydro-beta-carbolines in the presence of nitrite: HPLC-MS analysis of the reaction products. | Journal of agricultural and food chemistry 20011201 |
| Genotoxic effects of the alkaloids harman and harmine assessed by comet assay and chromosome aberration test in mammalian cells in vitro. | Pharmacology & toxicology 20011201 |
| Spasmolytic effects of three harmala alkaloids on guinea-pig isolated trachea. | Pharmacology & toxicology 20011101 |
| [Neurochemical characteristics of the ventromedial hypothalamus and anti-aversive effects of anxiolytic agents in various anxiety models]. | Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20010901 |
| Stimulatory effect of harmane and other beta-carbolines on locus coeruleus neurons in anaesthetized rats. | Neuroscience letters 20010810 |
| Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives. | Journal of natural products 20010701 |
| Identification of co-mutagenic chlorinated harmans in final effluent from a sewage treatment plant. | Mutation research 20010405 |
| Hydrogen bonding NH/pi interactions between betacarboline and methyl benzene derivatives. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20010401 |
| Evaluation of pyridoindoles, pyridylindoles and pyridylpyridoindoles as matrices for ultraviolet matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | Rapid communications in mass spectrometry : RCM 20010101 |
| Effects of beta- and gamma-carboline derivatives of DNA topoisomerase activities. | Mutation research 19960201 |
| Anticonvulsant effects of caerulein, cholecystokinin octapeptide (CCK-8) and diazepam against seizures produced in mice by harman, thiosemicarbazide and isoniazid. | Neuroscience letters 19810702 |
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