1-methyl-7-methoxy-b-carboline

CAS: 442-51-3 C13 H12 N2 O MW: 212.25184000

Identification

Nameharmine
IUPAC7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
CAS Number442-51-3
EINECS207-131-4
FDA UNII4FHH5G48T7
Molecular FormulaC13 H12 N2 O
Molecular Weight212.25184000
MDL NumberMFCD00004958
Nikkaji NumberJ11.378F
Beilstein0178813
XlogP33.60 (est)

Regulatory

Physical Properties

Assay 97.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 260.00 to 262.00 °C. @ 760.00 mm Hg
Boiling Point 421.40 °C. @ 760.00 mm Hg (est)
Flash Point 284.00 °F. TCC ( 139.80 °C. ) (est)
logP (o/w) 3.560
Soluble in water, 2.676 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintravenous-cat LDLo 10 mg/kg
Dermal Toxicitysubcutaneous-frog LDLo 300 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for harmine usage levels up tonot for fragrance use.
Recommendation for harmine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

passion fruit rue wild rue seeds

Synonyms

banisterin banisterine 7- methoxy-1-methyl-9H-b-carboline 7- methoxy-1-methyl-9H-pyrido(3,4-b)indole 7- methoxy-1-methyl-9H-pyrido[3,4-b]indole 7- methoxy-1-methyl-9H-pyrido[3,4-b]indole, 9CI 1- methyl-7-methoxy-b-carboline 9H- pyrido(3,4-b)indole, 7-methoxy-1-methyl- 9H- pyrido[3,4-b]indole-, 7-methoxy-1-methyl- 9H- pyrido[3,4-b]indole, 7-methoxy-1-methyl- telepathine yagein yageine PubMed: Inhibition of monoamine oxidase (MAO) by β-carbolines and their interactions in live neuronal (PC12) and liver (HuH-7 and MH1C1) cells. PubMed: Dietary vitamin E effects on the formation of heterocyclic amines in grilled lean beef. PubMed: Suggesting a possible role of CA1 histaminergic system in harmane-induced amnesia. PubMed: Formation of heterocyclic amines in salami and ham pizza toppings during baking of frozen pizza. PubMed: Metabolic pathways of the psychotropic-carboline alkaloids, harmaline and harmine, by liquid chromatography/mass spectrometry and NMR spectroscopy. PubMed: Formation of heterocyclic amines during cooking of duck meat. PubMed: Involvement of the cholinergic system of CA1 on harmane-induced amnesia in the step-down passive avoidance test. PubMed: Inhibition of the bioactivation of the neurotoxin MPTP by antioxidants, redox agents and monoamine oxidase inhibitors. PubMed: Screening of non-polar heterocyclic amines in urine by microextraction in packed sorbent-fluorimetric detection and confirmation by capillary liquid chromatography. PubMed: Capillary liquid chromatography with diode array and mass spectrometry detection for heterocyclic aromatic amine determination in ready-to-eat food treated with electron-beam irradiation. PubMed: beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). PubMed: Electrospray MS-based characterization of beta-carbolines--mutagenic constituents of thermally processed meat. PubMed: Hollow fibre-supported liquid membrane extraction and LC-MS/MS detection for the analysis of heterocyclic amines in urine samples. PubMed: Effects of beta-carboline harmine on behavioral and physiological parameters observed in the chronic mild stress model: further evidence of antidepressant properties. PubMed: Non-competitive androgen receptor inhibition in vitro and in vivo. PubMed: Simultaneous determination of thirteen plant alkaloids in a human specimen by SPE and HPLC. PubMed: Quantification of heterocyclic aromatic amines in fried meat by HPTLC/UV-FLD and HPLC/UV-FLD: a comparison of two methods. PubMed: Dietary epidemiology of essential tremor: meat consumption and meat cooking practices. 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: Factors influencing the norharman and harman contents in espresso coffee. PubMed: Differential effects of dopamine melanin on norharman-induced toxicity in PC12 cells. PubMed: Efficacy of planar chromatography coupled to (tandem) mass spectrometry for employment in trace analysis. PubMed: Blood harmane concentrations and dietary protein consumption in essential tremor. PubMed: Norharman-induced motoric impairment in mice: neurodegeneration and glial activation in substantia nigra. PubMed: Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke. PubMed: Modulation of cytochrome P450 1A1 by food-derived heterocyclic aromatic amines. PubMed: Exposure to beta-carbolines norharman and harman. PubMed: Elevation of blood beta-carboline alkaloids in essential tremor. PubMed: Tetrahydro-beta-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay. PubMed: Identification and occurrence of the bioactive beta-carbolines norharman and harman in coffee brews. PubMed: Natural variations of precursors in pig meat affect the yield of heterocyclic amines--effects of RN genotype, feeding regime, and sex. PubMed: Induction of sister chromatid exchanges and chromosome aberrations in cultured mammalian cells treated with aminophenylnorharman formed by norharman with aniline. PubMed: Genotoxic effects of the alkaloids harman and harmine assessed by comet assay and chromosome aberration test in mammalian cells in vitro. PubMed: Toxicokinetics of tremorogenic natural products, harmane and harmine, in male Sprague-Dawley rats. PubMed: Degradation of tetrahydro-beta-carbolines in the presence of nitrite: HPLC-MS analysis of the reaction products. PubMed: Tetrahydro-beta-carboline-3-carboxylic acid compounds in fish and meat: possible precursors of co-mutagenic beta-carbolines norharman and harman in cooked foods. PubMed: [In vitro study of the interference of certain food components with the metabolism of aflatoxin B1]. PubMed: [In vivo studies of the inhbitory effect of various food components on aflatoxin B1 metabolism]. PubMed: Formation of the comutagenic beta-carboline norharman in a simple tryptophan-containing model system at low temperature (40 degrees C-80 degrees C). PubMed: Determination of harmane and harmine in human blood using reversed-phased high-performance liquid chromatography and fluorescence detection. PubMed: Antiplatelet activity of soy sauce as functional seasoning. PubMed: Quantification of the co-mutagenic beta-carbolines, norharman and harman, in cigarette smoke condensates and cooked foods. PubMed: Analysis of nonpolar heterocyclic amines in cooked foods and meat extracts using gas chromatography-mass spectrometry. PubMed: Effects of negative allosteric modulators of gamma-aminobutyric acidA receptors on complex behavioral processes in monkeys. PubMed: Increased alcohol intake in low alcohol drinking rats after chronic infusion of the beta-carboline harman into the hippocampus. PubMed: Studies on the mechanism of intestinal passage of the food comutagen harman, in the rabbit. PubMed: [Effects of harman and norharman on aflatoxin B1 and aminopyrine metabolism by phenobarbital and 3-methylcholanthrene-induced rat liver microsomes]. PubMed: Effects of harmane on growth and in vivo metabolism of aflatoxin B1 in male and female rats. PubMed: Determination of beta-carbolines in foodstuffs by high-performance liquid chromatography and high-performance liquid chromatography-mass spectrometry. PubMed: The influence of dietaryβ-carboline alkaloids on growth rate, food consumption, and food utilization of larvae ofSpodoptera exigua (Hubner). PubMed: Mutagenicity, comutagenicity, and antimutagenicity of erythrosine (FD and C red 3), a food dye, in the Ames/Salmonella assay. PubMed: [The elimination of disorders in the acquisition of a conditioned active avoidance reaction by using the C-termination fragment of lysyl vasopressin]. PubMed: Mutagenicities of nitrosated carboline derivatives. PubMed: Food-borne amines and amides as potential precursors of endogenous carcinogens. PubMed: Alteration of mutagenic potentials by peroxidase, catalase, and superoxide dismutase. PubMed: Possible genotoxic carcinogens in foods in relation to cancer causation. PubMed: Use of pentachlorophenol as long-term inhibitor of sulfation of phenols and hydroxamic acids in the rat in vivo. PubMed: Carcinogenic, Mutagenic, and Comutagenic Aromatic Amines in Human Foods.