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442-51-3

442-51-3 | 9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl-

CAS No: 442-51-3 Catalog No: AG00I8E6 MDL No:MFCD00004958

Product Description

Catalog Number:
AG00I8E6
Chemical Name:
9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl-
CAS Number:
442-51-3
Molecular Formula:
C13H12N2O
Molecular Weight:
212.2472
MDL Number:
MFCD00004958
IUPAC Name:
7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
InChI:
InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
InChI Key:
BXNJHAXVSOCGBA-UHFFFAOYSA-N
SMILES:
COc1ccc2c(c1)[nH]c1c2ccnc1C
EC Number:
207-131-4
UNII:
4FHH5G48T7

Properties

Complexity:
258  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
212.095g/mol
Formal Charge:
0
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
212.252g/mol
Monoisotopic Mass:
212.095g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
37.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.6  

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Antitumor activity of 6-(cyclohexylamino)-1, 3-dimethyl-5(2-pyridyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione and Its Ti(IV), Zn(II), Fe(III), and Pd(II) complexes on K562 and Jurkat cell lines. Bioinorganic chemistry and applications 20080101
Effect of norharmane in vitro on juvenile hormone epoxide hydrolase activity in the lower termite, Reticulitermes speratus. Journal of insect science (Online) 20080101
The selectivity of protein kinase inhibitors: a further update. The Biochemical journal 20071215
Direct experimental evidence for a heterogeneous reaction of ozone with bromide at the air-aqueous interface. The journal of physical chemistry. A 20071004
Role of acetaldehyde in tobacco smoke addiction. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20071001
Coupled hydrogen-bonding interactions between beta-carboline derivatives and acetic acid. Magnetic resonance in chemistry : MRC 20071001
Biodistribution and radiation dosimetry of 11C-harmine in baboons. Nuclear medicine communications 20070901
Sustained inhibition of brotizolam induced anterograde amnesia by norharmane and retrograde amnesia by L-glutamic acid in mice. Behavioural brain research 20070822
Blood harmane is correlated with cerebellar metabolism in essential tremor: a pilot study. Neurology 20070807
Effects of ayahuasca on psychometric measures of anxiety, panic-like and hopelessness in Santo Daime members. Journal of ethnopharmacology 20070725
Differential effects of dopamine melanin on norharman-induced toxicity in PC12 cells. Journal of neural transmission (Vienna, Austria : 1996) 20070701
Antioxidant properties of beta-carboline alkaloids are related to their antimutagenic and antigenotoxic activities. Mutagenesis 20070701
A study on the antitumoral and differentiation effects of peganum harmala derivatives in combination with ATRA on leukaemic cells. Archives of pharmacal research 20070701
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
Targeting fat to prevent diabetes. Cell metabolism 20070501
The small molecule harmine is an antidiabetic cell-type-specific regulator of PPARgamma expression. Cell metabolism 20070501
Surfactant chain-length-dependent modulation of the prototropic transformation of a biological photosensitizer: norharmane in anionic micelles. Langmuir : the ACS journal of surfaces and colloids 20070424
Solid-phase fluorescence and ionization efficiency in negative-ion matrix-assisted laser desorption/ionization of neutral oligosaccharides: interaction between beta-carboline matrix and ammonium salt. Journal of the American Society for Mass Spectrometry 20070401
Factors influencing the norharman and harman contents in espresso coffee. Journal of agricultural and food chemistry 20070307
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. Analytica chimica acta 20070307
Detection of aminophenylnorharman, a possible endogenous mutagenic and carcinogenic compound, in human urine samples. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070101
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
A quantitative synthesis of the medicinal ethnobotany of the Malinké of Mali and the Asháninka of Peru, with a new theoretical framework. Journal of ethnobiology and ethnomedicine 20070101
Analysis of hallucinogenic constituents in Amanita mushrooms circulated in Japan. Forensic science international 20061220
The important role of Bcrp (Abcg2) in the biliary excretion of sulfate and glucuronide metabolites of acetaminophen, 4-methylumbelliferone, and harmol in mice. Molecular pharmacology 20061201
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. The Journal of pharmacology and experimental therapeutics 20061201
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. Journal of molecular graphics & modelling 20061101
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
Elevated monoamine oxidase a levels in the brain: an explanation for the monoamine imbalance of major depression. Archives of general psychiatry 20061101
Effects of beta-carboline alkaloids on the object recognition task in mice. Life sciences 20061026
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
Inhibition of neuronal nitric oxide synthase activity by N1-acetyl-5-methoxykynuramine, a brain metabolite of melatonin. Journal of neurochemistry 20060901
Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts. Analytica chimica acta 20060811
Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta. Pharmacological research 20060801
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
Protective effects of Peganum harmala L. extract, harmine and harmaline against human low-density lipoprotein oxidation. The Journal of pharmacy and pharmacology 20060701
Phytochemical and pharmacological study of roots and leaves of Guiera senegalensis J.F. Gmel (Combretaceae). Journal of ethnopharmacology 20060630
Effect of monoamine oxidase inhibition on amphetamine-evoked changes in dopamine receptor availability in the living pig: a dual tracer PET study with [11C]harmine and [11C]raclopride. Synapse (New York, N.Y.) 20060601
Identification of norharman as the cytotoxic compound produced by the sponge (Hymeniacidon perleve)-associated marine bacterium Pseudoalteromonas piscicida and its apoptotic effect on cancer cells. Biotechnology and applied biochemistry 20060601
[Harmine induces apoptosis in human SGC-7901 cells]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20060601
Norharman-induced motoric impairment in mice: neurodegeneration and glial activation in substantia nigra. Journal of neural transmission (Vienna, Austria : 1996) 20060301
Positron emission tomography quantification of [11C]-harmine binding to monoamine oxidase-A in the human brain. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20060301
In vitro and ex vivo distribution of [3H]harmane, an endogenous beta-carboline, in rat brain. Neuropharmacology 20060301
Preparation, structure and spasmolytic activities of some derivatives of harmine series of alkaloids. Natural product research 20060301
Autoradiographical distribution of imidazoline binding sites in monoamine oxidase A deficient mice. Journal of neurochemistry 20060301
Effect of chlorine as substituent on the photochemistry and acid-base properties of beta-carboline alkaloids. Journal of photochemistry and photobiology. B, Biology 20060201
Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. Life sciences 20060118
Antialgal, antibacterial and antifungal activity of two metabolites produced and excreted by cyanobacteria during growth. Microbiological research 20060101
Centrally acting imidazolines stimulate vascular alpha 1A-adrenergic receptors in Rat-Tail Artery. Cellular and molecular neurobiology 20060101
DNA binding properties of 9-substituted harmine derivatives. Biochemical and biophysical research communications 20051223
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
Simultaneous determination of nineteen hallucinogenic tryptamines/beta-calbolines and phenethylamines using gas chromatography-mass spectrometry and liquid chromatography-electrospray ionisation-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051015
Design, synthesis and in vitro and in vivo antitumor activities of novel beta-carboline derivatives. European journal of medicinal chemistry 20051001
Isolation and characterization of norharmane from Reticulitermes termites (Isoptera: Rhinotermitidae). Journal of economic entomology 20051001
Depressant effect of mitochondrial respiratory complex inhibitors on proteasome inhibitor-induced mitochondrial dysfunction and cell death in PC12 cells. Neurochemical research 20050901
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. European journal of pharmacology 20050822
Blood harmane concentrations and dietary protein consumption in essential tremor. Neurology 20050809
Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent. Phytochemistry 20050701
Photochemistry of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O (8-bromo-nor-harmane) and other bromo-beta-carbolines. Journal of photochemistry and photobiology. B, Biology 20050701
Antibacterial activity of 1-methyl-7-methoxy-beta-carboline and its phenacyl and coumarine analogues. Pakistan journal of pharmaceutical sciences 20050701
Prediction of genotoxicity of chemical compounds by statistical learning methods. Chemical research in toxicology 20050601
Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis. Journal of psychoactive drugs 20050601
Various alkaloid profiles in decoctions of Banisteriopsis caapi. Journal of psychoactive drugs 20050601
Fast and slow metabolizers of Hoasca. Journal of psychoactive drugs 20050601
Antitumor and neurotoxic effects of novel harmine derivatives and structure-activity relationship analysis. International journal of cancer 20050501
[DNA and chemical analyses of commercial fly agaric-related products]. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20050401
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. Journal of clinical neurology (Seoul, Korea) 20050401
Encapsulation of norharmane in cyclodextrin: formation of 1:1 and 1:2 inclusion complexes. Journal of photochemistry and photobiology. B, Biology 20050301
Lack of combination hepatocarcinogenicity of harman, norharman and amitrole when given with NaNO2 in the rat. The Journal of toxicological sciences 20050201
Photophysics in motionally constrained bioenvironment: interaction of norharmane with bovine serum albumin. Photochemistry and photobiology 20050101
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
Beta-carboline and quinoline alkaloids in root cultures and intact plants of Peganum harmala. Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101
Comprehensive photochemistry and photophysics of land- and marine-based beta-carbolines employing time-resolved emission and flash transient spectroscopy. Photochemistry and photobiology 20050101
Antimicrobial activity and main chemical composition of two smoke condensates from Peganum harmala seeds. Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101
A fatal intoxication following the ingestion of 5-methoxy-N,N-dimethyltryptamine in an ayahuasca preparation. Journal of analytical toxicology 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
Carcinogenicity of aminophenylnorharman, a possible novel endogenous mutagen, formed from norharman and aniline, in F344 rats. Carcinogenesis 20041001
Norharman and alcohol-dependency in male Wistar rats. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20041001
Tacrolimus-induced neurotoxicity and nephrotoxicity is ameliorated by administration in the dark phase in rats. Cellular and molecular neurobiology 20041001
Protective effect of 1-methylated beta-carbolines against 3-morpholinosydnonimine-induced mitochondrial damage and cell viability loss in PC12 cells. Neurochemical research 20041001
Synthesis, acute toxicities, and antitumor effects of novel 9-substituted beta-carboline derivatives. Bioorganic & medicinal chemistry 20040901
Identification of cytochrome P-450s involved in the formation of APNH from norharman with aniline. Mutation research 20040808
Antibiotic-mediated release of tumour necrosis factor alpha and norharman in patients with hospital-acquired pneumonia and septic encephalopathy. Intensive care medicine 20040801
Modulation of cytochrome P450 1A1 by food-derived heterocyclic aromatic amines. Toxicology 20040701
Dopamine transporter-mediated cytotoxicity of beta-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake. Journal of neurochemistry 20040501
Photophysics of norharmane in micellar environments: a fluorometric study. Biophysical chemistry 20040501
Specific inhibition of cyclin-dependent kinases and cell proliferation by harmine. Biochemical and biophysical research communications 20040423
Pi-delocalized beta-carbolinium cations as potential antimalarials. Bioorganic & medicinal chemistry letters 20040405
Effects of ayahuasca on binocular rivalry with dichoptic stimulus alternation. Psychopharmacology 20040401
Transport of harman alkaloids across Caco-2 cell monolayers. Chemical & pharmaceutical bulletin 20040401
Harmine: evaluation of its antileishmanial properties in various vesicular delivery systems. Journal of drug targeting 20040401
Exposure to beta-carbolines norharman and harman. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040325
Binding of beta-carbolines at imidazoline I2 receptors: a structure-affinity investigation. Bioorganic & medicinal chemistry letters 20040223
Trypanocidal constituents in plants 3. Leaves of Garcinia intermedia and heartwood of Calophyllum brasiliense. Biological & pharmaceutical bulletin 20040101
In vitro activity of the beta-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum. Experimental parasitology 20040101
Ultrastructural changes induced in HeLa cells after phototoxic treatment with harmine. Journal of applied toxicology : JAT 20040101
Binding of beta-carbolines at 5-HT(2) serotonin receptors. Bioorganic & medicinal chemistry letters 20031215
Effects of the beta-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans. European journal of pharmacology 20031215
Potent genotoxicity of aminophenylnorharman, formed from non-mutagenic norharman and aniline, in the liver of gpt delta transgenic mouse. Carcinogenesis 20031201
Craving for cigarettes among low and high dependent smokers: impact of norharman. Addiction biology 20031201
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
Possibility of the involvement of 9H-pyrido[3,4-b]indole (norharman) in carcinogenesis via inhibition of cytochrome P450-related activities and intercalation to DNA. Mutation research 20031110
Effects of harman and harmine on naloxone-precipitated withdrawal syndrome in morphine-dependent rats. Life sciences 20030919
Binding of tetrahydrocarboline derivatives at human 5-HT5A receptors. Journal of medicinal chemistry 20030828
Detection and characterization of cyclodextrin complexes with beta-carboline derivatives by spectroscopic techniques. Journal of pharmaceutical and biomedical analysis 20030808
Demonstration of high monoaminoxidase-A levels in neuroendocrine gastroenteropancreatic tumors in vitro and in vivo-tumor visualization using positron emission tomography with 11C-harmine. Nuclear medicine and biology 20030801
Human pharmacology of ayahuasca: subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics. The Journal of pharmacology and experimental therapeutics 20030701
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
Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism. Pharmacology, biochemistry, and behavior 20030601
Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic beta-carboline alkaloids harmaline and harmine. The Journal of pharmacology and experimental therapeutics 20030401
11C-harmine as a potential PET tracer for ductal pancreas cancer: in vitro studies. European radiology 20030401
Sulfate conjugating and transport functions of MDCK distal tubular cells. Kidney international 20030301
HPLC method for the analysis of harmol, harmalol, harmine and harmaline in the seeds of Peganum harmala L. Journal of pharmaceutical and biomedical analysis 20030226
Isolation and identification of two [(3)H]norharman- ([(3)H]beta-carboline)-binding proteins from rat liver. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030125
Identification of harman as the antibiotic compound produced by a tunicate-associated bacterium. Marine biotechnology (New York, N.Y.) 20030101
Effects of the Amazonian psychoactive beverage Ayahuasca on binocular rivalry: interhemispheric switching or interhemispheric fusion? Journal of psychoactive drugs 20030101
Synthesis of some phenacyl derivatives of 1-methyl-7-methoxy-beta-carboline and their behavioural study. Pakistan journal of pharmaceutical sciences 20030101
Elevation of blood beta-carboline alkaloids in essential tremor. Neurology 20021224
Inhibitors alter the spectrum and redox properties of monoamine oxidase A. Biochimica et biophysica acta 20021216
Sphingolipids from Conyza canadensis. Phytochemistry 20021201
Determination of N,N-dimethyltryptamine and beta-carboline alkaloids in human plasma following oral administration of Ayahuasca. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20021105
Exudation of fluorescent beta-carbolines from Oxalis tuberosa L roots. Phytochemistry 20021101
Identification of brain proteins that interact with 2-methylnorharman. An analog of the parkinsonian-inducing toxin, MPP+. Neuroscience research 20021101
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
Structure of DNA adduct formed with aminophenylnorharman, being responsible for the comutagenic action of norharman with aniline. Chemical research in toxicology 20021001
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline. Mutation research 20020930
Trypanocidal constituents in plants 1. Evaluation of some Mexican plants for their trypanocidal activity and active constituents in Guaco, roots of Aristolochia taliscana. Biological & pharmaceutical bulletin 20020901
Dynamic study of excited state hydrogen-bonded complexes of harmane in cyclohexane-toluene mixtures. Photochemistry and photobiology 20020901
Collective poisoning with hallucinogenous herbal tea. Forensic science international 20020814
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
Thermodynamic study of small hydrophobic ions at the water-lipid interface. Journal of colloid and interface science 20020701
Affinitive separation and on-line identification of antitumor components from Peganum nigellastrum by coupling a chromatographic column of target analogue imprinted polymer with mass spectrometry. Analytical chemistry 20020515
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
Beta-carbolines as specific inhibitors of cyclin-dependent kinases. Bioorganic & medicinal chemistry letters 20020408
Induction of sister chromatid exchanges and chromosome aberrations in cultured mammalian cells treated with aminophenylnorharman formed by norharman with aniline. Mutation research 20020325
Genotoxic and recombinogenic activities of the two beta-carboline alkaloids harman and harmine in Saccharomyces cerevisiae. Mutation research 20020320
Maternal and developmental toxicity in mice by aminophenylnorharman, formed from norharman and aniline. Human & experimental toxicology 20020301
The impact of smoking and drinking on plasma levels of norharman. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20020201
Synergistic in vitro antimalarial activity of plant extracts used as traditional herbal remedies in Mali. Parasitology research 20020201
An in vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. seeds extract and its beta-carboline alkaloids. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques 20020101
Interaction of folk medicinal plant extracts with human alpha2-adrenoceptor subtypes. Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101
An in vitro study on the kinetics, subcellular distribution and phototoxicity of harmine in human tumor cells. Bollettino chimico farmaceutico 20020101
[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
Effects of harmine on dopamine output and metabolism in rat striatum: role of monoamine oxidase-A inhibition. Psychopharmacology 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
Pharmacokinetics of the beta-carboline norharman in man. Life sciences 20010921
Testicular toxicity in F344 rats by aminophenylnorharman, formed from norharman and aniline. Toxicology and applied pharmacology 20010901
[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
Oxidative DNA damage by an N-hydroxy metabolite of the mutagenic compound formed from norharman and aniline. Mutation research 20010725
Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives. Journal of natural products 20010701
Structures of mutagens produced by the co-mutagen norharman with o- and m-toluidine isomers. Mutation research 20010627
The acute effects of norharman on cocaine self-administration and sensorimotor function in male Wistar rats. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20010601
Tryptophan: a precursor for the endogenous synthesis of norharman in man. Neuroscience letters 20010511
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. The European journal of neuroscience 20010501
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
Comparative study on the vasorelaxant effects of three harmala alkaloids in vitro. Japanese journal of pharmacology 20010301
Norharman, an indoleamine-derived beta-carboline, but not Trp-P-2, a gamma-carboline, induces apoptotic cell death in human neuroblastoma SH-SY5Y cells. Journal of neural transmission (Vienna, Austria : 1996) 20010101
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
Pharmepéna-Psychonautics: Human intranasal, sublingual and oral pharmacology of 5-methoxy-N,N-dimethyl-tryptamine. Journal of psychoactive drugs 20010101
Steroid hormone activity of flavonoids and related compounds. Breast cancer research and treatment 20000701
Synthesis of some 11C-labelled MAO-A inhibitors and their in vivo uptake kinetics in rhesus monkey brain. Nuclear medicine and biology 19970701
Effects of beta- and gamma-carboline derivatives of DNA topoisomerase activities. Mutation research 19960201
Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies. Journal of medicinal chemistry 19930430
Studies on the mechanism of chlordecone-induced tremor in rats. Neurotoxicology 19850101
Inhibition of indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by beta-carboline and indole derivatives. Archives of biochemistry and biophysics 19840801
Inhibition of benzodiazepine and GABA receptor binding by amino-gamma-carbolines and other amino acid pyrolysate mutagens. European journal of pharmacology 19840210
Anticonvulsant effects of caerulein, cholecystokinin octapeptide (CCK-8) and diazepam against seizures produced in mice by harman, thiosemicarbazide and isoniazid. Neuroscience letters 19810702
Anti-tremor action of C10Dichol, a peripheral acetylcholine synthesis inhibitor. British journal of pharmacology 19800101

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