EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes


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CAS Number: 442-51-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-131-4
Nikkaji Web:J11.378F
Beilstein Number:0178813
XlogP3:3.60 (est)
Molecular Weight:212.25184000
Formula:C13 H12 N2 O
BioActivity Summary:listing
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
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
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)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
Alfa Biotechnology
For experimental / research use only.
Harmine  98%
BOC Sciences
For experimental / research use only.
Harmine >98%
Odor: characteristic
Use: Harmine induces apoptosis and inhibits proliferation, migration and invasion of human gastric cancer cells, which may be mediated by down-regulation of COX-2 expression.
For experimental / research use only.
Harmine from Plants ≥98%
For experimental / research use only.
Harmine (HPLC) ≥95%
Glentham Life Sciences
Santa Cruz Biotechnology
For experimental / research use only.
Harmine ≥97%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Harmine 98%
For experimental / research use only.
Harmine >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
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-cat LDLo 10 mg/kg
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.

intramuscular-man TDLo 3 mg/kg
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.

intravenous-mouse LDLo 50 mg/kg
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.

intravenous-rabbit LDLo 60 mg/kg
Neuropharmacology. Vol. 10, Pg. 15, 1971.

Dermal Toxicity:
subcutaneous-frog LDLo 300 mg/kg
Quarterly Journal of Pharmacy & Pharmacology. Vol. 9, Pg. 37, 1936.

subcutaneous-guinea pig LDLo 100 mg/kg
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.

subcutaneous-mouse LD50 243 mg/kg
Pharmaceutical Chemistry Journal Vol. 10, Pg. 1171, 1976.

subcutaneous-rabbit LDLo 200 mg/kg
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.

subcutaneous-rat LD50 200 mg/kg
Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.

Inhalation Toxicity:
Not determined
Safety in Use Information:
natural substances and extractives
Recommendation for harmine usage levels up to:
 not for fragrance use.
Recommendation for harmine 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 :5280953
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
RTECS:UV0175000 for cas# 442-51-3
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5280953
Pubchem (sid):134974844
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
KEGG (GenomeNet):C06538
HMDB (The Human Metabolome Database):HMDB30311
Export Tariff Code:2933.39.9100
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 passion fruit
Search Trop Picture
 rue wild rue seeds
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7-methoxy-1-methyl-9H-pyrido[3,4-b]indole, 9CI
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-


PubMed:Inhibition of monoamine oxidase (MAO) by ╬▓-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 dietary╬▓-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.
alkaloid isolated from seeds of peganum harmala l., zygophyllaceae. it is identical to banisterine, or telepathine, from banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western amazon region from related plants. it has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic parkinson disease in the 1920's. Alkaloid from Passiflora edulis (passionfruit)
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