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2-methyl indole
indole, 2-methyl-

Supplier Sponsors

Name:2-methyl-1H-indole
CAS Number: 95-20-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:202-398-3
FDA UNII: I7CN58827I
Nikkaji Web:J3.949G
Beilstein Number:0109781
MDL:MFCD00005616
XlogP3:2.50 (est)
Molecular Weight:131.17773000
Formula:C9 H9 N
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
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PubMed:Search
NCBI:Search
DG SANTE Food Flavourings:14.131 2-methylindole
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 59.00 to 61.00 °C. @ 760.00 mm Hg
Boiling Point: 271.00 to 273.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.010000 mmHg @ 25.00 °C. (est)
Flash Point: 286.00 °F. TCC ( 141.11 °C. )
logP (o/w): 2.530
Soluble in:
 alcohol
 water, 628.4 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor Type: animal
animal naphthyl
Odor Description:at 0.10 % in dipropylene glycol. animal indole fresher than skatole with no fecal odor
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
2-Methyl-1H-indole >99.0%(GC)
BST Tianjin Co.
2-Methylindole
EMD Millipore
For experimental / research use only.
2-Methylindole
sds
Santa Cruz Biotechnology
For experimental / research use only.
2-Methylindole >98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
2-Methylindole 98%
sds
TCI AMERICA
For experimental / research use only.
2-Methylindole >99.0%(GC)
sds
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
S 01/02 - Keep locked up and out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
 
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
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 > 262 mg/kg
Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1620, 1974.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for 2-methyl indole usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.0012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 400 (μg/person/day)
Threshold of Concern:90 (μg/person/day)
Structure Class: III
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.400002.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.200001.00000
Edible ices, including sherbet and sorbet (03.0): 0.400002.00000
Processed fruit (04.1): 0.400002.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 1.000005.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 2.0000010.00000
Meat and meat products, including poultry and game (08.0): 0.200001.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.200001.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.100000.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.200001.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): --
Ready-to-eat savouries (15.0): 1.000005.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.200001.00000
 
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 24 (FGE.24): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 Flavouring Group Evaluation 24, Revision 1 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 77 (FGE77) [1] - Consideration of Pyridine, Pyrrole and Quinoline Derivatives evaluated by JECFA (63rd meeting) structurally related to Pyridine, Pyrrole, Indole and Quinoline Derivatives evaluated by EFSA in FGE.24Rev1 (2008)
View page or View pdf

Scientific opinion on Flavouring Group Evaluation 24, Revision 2 (FGE.24Rev2): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):95-20-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7224
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-methyl-1H-indole
Chemidplus:0000095205
RTECS:NM0345000 for cas# 95-20-5
 
References:
 2-methyl-1H-indole
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):7224
Pubchem (sid):134971596
 
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
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.90.8300
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 indole, 2-methyl-
2-methyl-1H-indole
2-methylindole
 

Articles:

PubMed:2-Methylindole as an indicative nucleophile for developing a three-component reaction of aldehyde with two different nucleophiles.
PubMed:Functionalization of benzylic C(sp(3))-H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis.
PubMed:Rh(III)-catalyzed tandem C-H allylation and oxidative cyclization of anilides: a new entry to indoles.
PubMed:Biochemical and pharmacological characterization of AZD1981, an orally available selective DP2 antagonist in clinical development for asthma.
PubMed:An efficient one pot syntheses of aryl-3,3'-bis(indolyl)methanes and studies on their spectral characteristics, DPPH radical scavenging-, antimicrobial-, cytotoxicity-, and antituberculosis activity.
PubMed:3-(1,2-Di-p-tolyl-vin-yl)-2-methyl-1H-indole.
PubMed:1-(4-Meth-oxy-phen-yl)-2-methyl-1H-indole-3-carbonitrile.
PubMed:1-(4-Bromo-phen-yl)-2-methyl-1H-indole-3-carbonitrile.
PubMed:Synthesis under microwave irradiation of [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazoles and other diazoles bearing indole moieties and their antimicrobial evaluation.
PubMed:1-(2-Chloro-phenyl)-6-fluoro-2-methyl-1H-indole-3-carbonitrile.
PubMed:Discovery of selective indole-based prostaglandin Dâ‚‚ receptor antagonist.
PubMed:Real-time reaction monitoring using ion mobility-mass spectrometry.
PubMed:Synthetic studies on indolocarbazoles: total synthesis of staurosporine aglycon.
PubMed:Free radical-scavenging activity and DNA damaging potential of auxins IAA and 2-methyl-IAA evaluated in human neutrophils by the alkaline comet assay.
PubMed:A platform of high-density INDEL/CAPS markers for map-based cloning in Arabidopsis.
PubMed:Bioactivation of a novel 2-methylindole-containing dual chemoattractant receptor-homologous molecule expressed on T-helper type-2 cells/D-prostanoid receptor antagonist leads to mechanism-based CYP3A inactivation: glutathione adduct characterization and prediction of in vivo drug-drug interaction.
PubMed:tert-Butyl 3-(8-bromo-4H,10H-1,2-oxazolo[4,3-c][1]benzoxepin-10-yl)-2-methyl-1H-indole-1-carboxyl-ate.
PubMed:The relevance of the collaborative effect in determining the performances of photorefractive polymer materials.
PubMed:Azolyacetones as precursors to indoles and naphthofurans facilitated by microwave irradiation with simultaneous cooling.
PubMed:Carbon nucleophilicities of indoles in S(N)Ar substitutions of superelectrophilic 7-chloro-4,6-dinitrobenzofuroxan and -benzofurazan.
PubMed:tert-Butyl 3-[2,2-bis-(ethoxy-carbon-yl)-vinyl]-2-methyl-1H-indole-1-carboxyl-ate.
PubMed:Unconditionally stable indole-derived glass blends having very high photorefractive gain: the role of intermolecular interactions.
PubMed:Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds.
PubMed:Chemically induced dimerization of human nonpancreatic secretory phospholipase A2 by bis-indole derivatives.
PubMed:Synthesis and pharmacological evaluation of peptide-mimetic protease-activated receptor-1 antagonists containing novel heterocyclic scaffolds.
PubMed:Development and validation of a method for simultaneous analysis of the boar taint compounds indole, skatole and androstenone in pig fat using liquid chromatography-multiple mass spectrometry.
PubMed:Isolation and identification of a major impurity in a new bulk drug candidate by preparative LC, ESI-MS(n), LC-MS-MS, and NMR.
PubMed:Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid.
PubMed:Effect of indole-3-acetic acid derivatives on neuroepithelium in rat embryos.
PubMed:Development of a prostaglandin D2 receptor antagonist: discovery of a new chemical lead.
PubMed:Identification of indole derivatives exclusively interfering with a G protein-independent signaling pathway of the prostaglandin D2 receptor CRTH2.
PubMed:Identification of natural dyes used in works of art by pyrolysis-gas chromatography/mass spectrometry combined with in situ trimethylsilylation.
PubMed:2- and 3-[(aryl)(azolyl)methyl]indoles as potential non-steroidal aromatase inhibitors.
PubMed:The reaction of indole with the aminoacrylate intermediate of Salmonella typhimurium tryptophan synthase: observation of a primary kinetic isotope effect with 3-[(2)H]indole.
PubMed:Discovery of a new class of potent, selective, and orally active prostaglandin D2 receptor antagonists.
PubMed:Development of prostaglandin D2 receptor antagonist: discovery of highly potent antagonists.
PubMed:Discovery of new chemical leads for prostaglandin D2 receptor antagonists.
PubMed:Discovery of orally active prostaglandin D2 receptor antagonists.
PubMed:Adsorption of indole and 2-methylindole on ligand-exchange matrix.
PubMed:Primary electron-transfer dynamics in 2-phenylindole-9-cyanoanthracene system. A comparative study with 2-methylindole.
PubMed:Endothelium-dependent noradrenergic hyperresponsiveness induced by thapsigargin in human saphenous veins: role of thromboxane and calcium.
PubMed:XAFS studies of anti-inflammatory dinuclear and mononuclear Zn(II) complexes of indomethacin.
PubMed:Novel reversible indole-3-carboxylate decarboxylase catalyzing nonoxidative decarboxylation.
PubMed:Isolation and characterization of anaerobic indole- and skatole-degrading bacteria from composting animal wastes.
PubMed:Relationship between structures of substituted indolic compounds and their degradation by marine anaerobic microorganisms.
PubMed:Fructooligosaccharides and Lactobacillus acidophilus modify bowel function and protein catabolites excreted by healthy humans.
PubMed:Nature of non-radiative processes involved in the excited state of 9-cyanoanthracene in presence of 2-methylindole/2-methylindoline quenchers. A laser flash photolysis study to reveal the medium effects.
PubMed:Unsymmetrical methylene derivatives of indoles as antiproliferative agents.
PubMed:Anti-Inflammatory Dinuclear Copper(II) Complexes with Indomethacin. Synthesis, Magnetism and EPR Spectroscopy. Crystal Structure of the N,N-Dimethylformamide Adduct.
PubMed:The oxidation of indole derivatives catalyzed by horseradish peroxidase is highly chemiluminescent.
PubMed:Determination of the structures of antiinflammatory copper(II) dimers of indomethacin by multiple-scattering analyses of X-ray absorption fine structure data.
PubMed:Syntheses and characterization of anti-inflammatory dinuclear and mononuclear zinc indomethacin complexes. Crystal structures of [Zn2(indomethacin)4(L)2] (L = N,N-dimethylacetamide, pyridine, 1-methyl-2-pyrrolidinone) and [Zn(indomethacin)2(L1)2] (L1 = ethanol, methanol).
PubMed:Nitric oxide accelerates the ascorbic acid-induced osteoblastic differentiation of mouse stromal ST2 cells by stimulating the production of prostaglandin E(2).
PubMed:Identification of binding sites of bopindolol and its two metabolites with beta1-adrenoceptors by molecular modeling: comparison with beta2 adrenoceptors.
PubMed:Induction of apoptotic DNA fragmentation by nonsteroidal anti-inflammatory drugs in cultured rat gastric mucosal cells.
PubMed:Anti-inflammatory drugs interacting with Zn(II), Cd(II) and Pt(II) metal ions.
PubMed:Endothelium-mediated and N omega-nitro-L-arginine methyl ester-sensitive responses to cromakalim and diazoxide in the rat mesenteric bed.
PubMed:Bopindolol is a slowly dissociating beta 1-adrenoceptor antagonist when compared to other beta-blockers.
PubMed:2-Methyl-L-tryptophan is a substrate of tryptophanase.
PubMed:Bromoacetamido analogs of indomethacin and mefenamic acid as affinity-labeling agents and mechanistic probes for prostaglandin H2 synthase.
PubMed:Solid-phase synthesis of cionin, a protochordate-derived octapeptide related to the gastrin/cholecystokinin family of peptides, and its mono-tyrosine-sulfate-containing derivatives.
PubMed:Spectroscopic studies of cutaneous photosensitizing agents. XVIII. Indomethacin.
PubMed:Evaluation of the final deprotection system for the solid-phase synthesis of Tyr(SO3H)-containing peptides with 9-fluorenylmethyloxycarbonyl (Fmoc)-strategy and its application to the synthesis of cholecystokinin (CCK)-12.
PubMed:Development of affinity labeling agents based on nonsteroidal anti-inflammatory drugs: labeling of the nonsteroidal anti-inflammatory drug binding site of 3 alpha-hydroxysteroid dehydrogenase.
PubMed:Degradation of substituted indoles by an indole-degrading methanogenic consortium.
PubMed:Beta-blocking potency and selectivity of bopindolol and its two metabolites for beta 1- and beta 2-adrenergic receptors as assessed by radioligand binding assay.
PubMed:Design, synthesis and antiinflammatory activity of a new indomethacin ester. 2-[N-[3-(3-(piperidinomethyl)phenoxy)propyl]carbamoylmethylthio]ethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-indole-3-acetate.
PubMed:Studies on antibacterial agents. II. Synthesis and antibacterial activities of substituted 1,2-dihydro-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids.
PubMed:Effects of Bay o 2752, a hypocholesterolemic agent, on intestinal taurocholate absorption and cholesterol esterification.
PubMed:Activity of melatonin and other pineal indoles on the in vitro synthesis of cortisol, cortisone, and adrenal androgens.
PubMed:Influence of N,N'-(1,11-undecandiyl) bis (2,3-dihydro-2-methyl-1H-indole-1-carboxamide) (BAY 02752) on gallstone formation and regression in hamsters.
PubMed:Inhibition of thromboxane formation in vivo and ex vivo: implications for therapy with platelet inhibitory drugs.
PubMed:Mutagenicities of indole and 30 derivatives after nitrite treatment.
PubMed:Synthesis of some indole derivatives with potential antiinflammatory activity.
PubMed:Inhibition of thromboxane synthetase by the imidazole derivative 3-(1H-imidazol-1-yl-methyl)-2-methyl-1H-indole-1-propanoic acid as a novel therapeutic approach to experimental myocardial ischemia.
PubMed:[Retard effect of acemetacin from a commercial preparation--kinetics in humans following single and multiple administration].
PubMed:Pharmacological profiles of 2-carboxyphenyl-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetate and 2-[(2-carboxyphenoxy)-carbonyl]phenyl-1-(4-chlorobenzoyl)-5-meth oxy-2- methylindole-3-acetate, new antiinflammatory agents.
PubMed:Selective thromboxane synthetase inhibitors. 2. 3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indole-1-propanoic acid and analogues.
PubMed:Nitrosatable precursors of mutagens in vegetables and soy sauce.
PubMed:Effect of inhibitors of the lipoxygenase pathway on mouse myoblast fusion.
PubMed:Effect of TEI-4120 (3-benzoyl-N-beta-ethoxyisopropyl-2-methlindole) on carrageenan induced disseminated intravascular coagulation (DIC) in rats.
PubMed:New synthetic inhibitors of chymotrypsin.
PubMed:Indomethacin inhibition of glutathione S-transferases.
PubMed:[2-Methylindoles substituted in the 1st, 3d and 5th positions and the diffuse neuroendocrine APUD system].
PubMed:Modification of the AOAC gas-liquid chromatographic method for indole in shrimp: collaborative study.
PubMed:Determination of thiabendazole and 5-hydroxythiabendazole in human serum by fluorescence-detected high-performance liquid chromatography.
PubMed:Free-radical damage to lipids, amino acids, carbohydrates and nucleic acids determined by thiobarbituric acid reactivity.
PubMed:High-pressure liquid chromatographic determination of ibuprofen in plasma.
PubMed:Clinical Pharmacokinetics of indomethacin.
PubMed:Ultraviolet detection procedure for liquid chromatographic determination of indole in shrimp.
PubMed:High pressure liquid chromatographic method for indole in shrimp: development of method and collaborative study.
PubMed:Oxygenation of indoles by a copper(I) chloride pyridine complex. A new tryptophan 2,3-dioxygenase model system.
PubMed:Structure of Cu2(indomethacin)4 and the reaction with superoxide in aprotic systems.
PubMed:Glycerides as prodrugs. 3. Synthesis and antiinflammatory activity of [1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetyl]glycerides (indomethacin glycerides).
PubMed:Binding sites for melatonin in bovine pineal gland.
PubMed:[Therapy of acute attacks of gout using acemetacin (author's transl)].
PubMed:[Controlled double blind study on the effectiveness and adverse effects of acemetacin and indomethacin in the treatment of psoriatic arthritis].
PubMed:[Controlled, double blind study of a possible interaction between acemetacin and a concomitant anticoagulant therapy].
PubMed:[Influence of acemetacin on DNA repair and DNA synthesis in vitro and in vivo (author's transl)].
PubMed:[Toxicology of acemetacin].
PubMed:[Metabolism and pharmacokinetics of acemetacin in man (author's transl)].
PubMed:[Comparative metabolic studies on [14C]-labelled acemetacin and indometacin in rats (author's transl)].
PubMed:[Anti-inflammatory action of acemetacin (author's transl)].
PubMed:[Chemical structure and anti-inflammatory activity in the group of substituted indole-3-acetic acids (author's transl)].
PubMed:[On the pharmacodynamics of acemetacin (author's transl)].
PubMed:[Analytical methods and in vitro studies with acemetacin].
PubMed:Peroxide oxidation of indole to oxindole by chloroperoxidase catalysis.
PubMed:Preparation, gas chromatography and mass spectrometry of methyl and trimethylsilyl esters of indomethacin.
PubMed:Studies on the metabolism of 5-hydroxytryptamine (serotonin). VII. Effects of haloindoles on cerebral 5-HT in various species.
PubMed:Pharmacokinetics of a new beta-adrenoceptor blocking agent, LF 17-895, in man.
PubMed:[Influence of indole-3-alkanecarboxylic acids on glucose utilization in rats].
PubMed:The therapeutic activity of 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid monohydrate glucosamide in rheumatoid arthritis (double blind trial).
PubMed:Substituted anilides of 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-indole-3-acetic acid.
PubMed:Crystal and molecular structure of an antiinflammatory agent, indomethacin, 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid.
PubMed:Physiologic disposition and metabolic fate of indomethacin analogs. II. 1-(p-chlorobenzoyl)-5-dimethylamino-2-methylindole-3-acetic acid.
PubMed:Isomeric Mannich bases derived from ethyl 5-hydroxy-2-methylindole-3-carboxylate.
PubMed:[On the pharmacology of 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole acetic acid, a new antiphlogistic agent].
PubMed:ANTI-INFLAMMATORY AND ANTIPYRETIC ACTIVITIES OF INDOMETHACIN, 1-(P-CHLOROBENZOYL)-5-METHOXY-2-METHYLINDOLE-3-ACETIC ACID.
PubMed:Effects on amine oxidase of substances which antagonize 5-hydroxytryptamine more than tryptamine on the rat fundus strip.
PubMed:Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations.
 
Notes:
skatole refers to 3-methylindole.
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