83-34-1 | 3-Methylindole

Packsize	Purity	Availability	Price	Discounted Price
5g	98%	in stock	$16.00	$11.00
10g	98%	in stock	$20.00	$14.00
25g	98%	in stock	$45.00	$31.00
100g	98%	in stock	$102.00	$71.00
500g	98%	in stock	$440.00	$308.00

Description

• Catalog Number: AB65383
• Chemical Name: 3-Methylindole
• CAS Number: 83-34-1
• Molecular Formula: C9H9N
• Molecular Weight: 131.17446
• MDL Number: MFCD00005627
• SMILES: Cc1c[nH]c2c1cccc2
• NSC Number: 122024

Computed Properties

• Complexity: 122
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Donor Count: 1
• XLogP3: 2.6

Literature

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• Cloning and mapping of the porcine cytochrome-p450 2E1 gene and its association with skatole levels in the domestic pig.

  Animal genetics 20051001

• Zafirlukast metabolism by cytochrome P450 3A4 produces an electrophilic alpha,beta-unsaturated iminium species that results in the selective mechanism-based inactivation of the enzyme.

  Chemical research in toxicology 20050901

• Characterization of odorants causing an atypical aroma in white pepper powder (Piper nigrum L.) based on quantitative measurements and orthonasal breakthrough thresholds.

  Journal of agricultural and food chemistry 20050727

• Role of the fermentation process in off-odorant formation in white pepper: on-site trial in Thailand.

  Journal of agricultural and food chemistry 20050727

• Insights into the role of the aromatic residue in galactose-binding sites: MP2/6-311G++** study on galactose- and glucose-aromatic residue analogue complexes.

  Biochemistry 20050614

• Dose-dependent effects of resistant potato starch in the diet on intestinal skatole formation and adipose tissue accumulation in the pig.

  Journal of veterinary medicine. A, Physiology, pathology, clinical medicine 20050601

• Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles.

  Bioorganic & medicinal chemistry 20050516

• Examining the risks and benefits of replacing traditional dose-response with hormesis.

  Human & experimental toxicology 20050501

• Free oestrone in adipose tissue and its relation to androstenone and skatole in entire male pigs.

  Reproduction in domestic animals = Zuchthygiene 20050401

• Effects of resistant potato starch on odor emission from feces in Swine production units.

  Journal of agricultural and food chemistry 20050223

• Bayesian analysis of quantitative trait loci for boar taint in a Landrace outbred population.

  Journal of animal science 20050201

• Detection of quantitative trait loci for androstenone, skatole and boar taint in a cross between Large White and Meishan pigs.

  Animal genetics 20050201

• Use of ultrasonic vocalizations to assess olfactory detection in mouse pups treated with 3-methylindole.

  Behavioural processes 20050131

• Chemical changes induced by methyl jasmonate in oilseed rape grown in the laboratory and in the field.

  Journal of agricultural and food chemistry 20041215

• Structure and function of the C-terminal domain of the polymerase cofactor of rabies virus.

  Journal of molecular biology 20041029

• Stark absorption spectroscopy of indole and 3-methylindole.

  The Journal of chemical physics 20040908

• Semiochemistry of the goldeneyed lacewing Chrysopa oculata: attraction of males to a male-produced pheromone.

  Journal of chemical ecology 20040901

• Selective tryptophan modification with rhodium carbenoids in aqueous solution.

  Journal of the American Chemical Society 20040825

• Molecular cloning, expression and functional characterization of the cytochrome P450 2A6 gene in pig liver.

  Animal genetics 20040801

• Age-related variation of plasma concentrations of skatole, androstenone, testosterone, oestradiol-17 beta, oestrone sulphate, dehydroepiandrosterone sulphate, triiodothyronine and IGF-1 in six entire male pigs.

  Reproduction in domestic animals = Zuchthygiene 20040601

• Excretion of major odor-causing and acidifying compounds in response to dietary supplementation of chicory inulin in growing pigs.

  Journal of animal science 20040601

• Use of a chemical trigger for electron transfer to characterize a precursor to cluster X in assembly of the iron-radical cofactor of Escherichia coli ribonucleotide reductase.

  Biochemistry 20040525

• Laboratory and field responses of the mosquito, Culex quinquefasciatus, to plant-derived Culex spp. oviposition pheromone and the oviposition cue skatole.

  Journal of chemical ecology 20040501

• A direct access to 3-(2-Oxoalkyl)indoles via aluminum chloride induced C-C bond formation.

  The Journal of organic chemistry 20040416

• Structural and catalytic diversity in the two family 11 aldo-keto reductases.

  Journal of molecular biology 20040326

• Mass analyzed threshold ionization spectroscopy of 5-methylindole and 3-methylindole cations and the methyl substitution effect.

  The Journal of chemical physics 20040315

• Molecular cloning and functional analysis of porcine SULT1A1 gene and its variant: a single mutation SULT1A1 causes a significant decrease in sulfation activity.

  Mammalian genome : official journal of the International Mammalian Genome Society 20040301

• Photoaffinity labeling identifies the substrate-binding site of mammalian squalene epoxidase.

  Biochemical and biophysical research communications 20040227

• Fat volatiles tracers of grass feeding in sheep.

  Meat science 20040201

• Environmental swap energy and role of configurational entropy in transfer of small molecules from water into alkanes.

  The Journal of chemical physics 20040115

• Study on the organoleptic intensity scale for measuring oral malodor.

  Journal of dental research 20040101

• (Z)-2-(1H-Indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one.

  Acta crystallographica. Section C, Crystal structure communications 20040101

• Evoked response to olfactory stimulations in anosmic patients.

  The international tinnitus journal 20040101

• Use of a novel group of oral malodor measurements to evaluate an anti-oral malodor mouthrinse (TriOralTM) in humans.

  The Journal of clinical dentistry 20040101

• Steady-state and time-resolved studies on the formation of skatolyl radicals photosensitized by 2-benzoylthiophene.

  Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20031101

• Field and laboratory evaluations of potential oviposition attractants for Aedes albopictus (Diptera: Culicidae).

  Journal of the American Mosquito Control Association 20030901

• Rapid formation of non-native contacts during the folding of HPr revealed by real-time photo-CIDNP NMR and stopped-flow fluorescence experiments.

  Journal of molecular biology 20030704

• 3-methylindole induces transient olfactory mucosal injury in ponies.

  Veterinary pathology 20030701

• Characterization of pulmonary CYP4B2, specific catalyst of methyl oxidation of 3-methylindole.

  Molecular pharmacology 20030501

• Phase II in vitro metabolism of 3-methylindole metabolites in porcine liver.

  Xenobiotica; the fate of foreign compounds in biological systems 20030501

• Time profile of putrescine, cadaverine, indole and skatole in human saliva.

  Archives of oral biology 20030401

• Identification of oxidation products and free radicals of tryptophan by mass spectrometry.

  Journal of the American Society for Mass Spectrometry 20030401

• Psychophysical evaluation of responses to pleasant and mal-odour stimulation in human subjects; adaptation, dose response and gender differences.

  International journal of psychophysiology : official journal of the International Organization of Psychophysiology 20030401

• Synthesis of 11C-amides using [11C]carbon monoxide and in situ activated amines by palladium-mediated carboxaminations.

  Organic & biomolecular chemistry 20030207

• 3-methylindole-induced toxicity to human bronchial epithelial cell lines.

  Toxicological sciences : an official journal of the Society of Toxicology 20030201

• Cholecystectomy and the risk for developing colorectal cancer and distal colorectal adenomas.

  British journal of cancer 20030113

• Solution structure of a circular-permuted variant of the potent HIV-inactivating protein cyanovirin-N: structural basis for protein stability and oligosaccharide interaction.

  Journal of molecular biology 20030103

• Hydantoin-substituted 4,6-dichloroindole-2-carboxylic acids as ligands with high affinity for the glycine binding site of the NMDA receptor.

  Journal of medicinal chemistry 20030102

• Fluorescence determination of tryptophan side-chain accessibility and dynamics in triple-helical collagen-like peptides.

  Biophysical journal 20030101

• Ultrastructural changes and olfactory deficits during 3-methylindole-induced olfactory mucosal necrosis and repair in mice.

  Ultrastructural pathology 20030101

• Lasting chemiluminescence of 3-indoleglyoxylyl chloride and its enhancement.

  Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20030101

• Effects of butyrate on apoptosis in the pig colon and its consequences for skatole formation and tissue accumulation.

  Journal of animal science 20030101

• Effects of feeding aspirin and supplemental vitamin E on plasma concentrations of 3-methylindole, 3-methyleneindolenine-adduct concentrations in blood and pulmonary tissues, lung lesions, and growth performance in feedlot cattle.

  American journal of veterinary research 20021201

• Development of the [3 + 2] annulations of cyclohexenylsilanes and chlorosulfonyl isocyanate: application to the total synthesis of (+/-)-peduncularine.

  Journal of the American Chemical Society 20020925

• Odor discrimination and odor quality perception in rats with disruption of connections between the olfactory epithelium and olfactory bulbs.

  The Journal of neuroscience : the official journal of the Society for Neuroscience 20020515

• Modifying rates of reductive elimination of leaving groups from indolequinone prodrugs: a key factor in controlling hypoxia-selective drug release.

  Biochemical pharmacology 20020501

• Cytochrome P450IIE1 (CYP2E1) is induced by skatole and this induction is blocked by androstenone in isolated pig hepatocytes.

  Chemico-biological interactions 20020420

• Time-dependent changes in plasma concentrations of 3-methylindole and blood concentrations of 3-methyleneindolenine-adduct in feedlot cattle.

  American journal of veterinary research 20020401

• Effects of fructooligosaccharide on conversion of L-tryptophan to skatole and indole by mixed populations of pig fecal bacteria.

  The Journal of general and applied microbiology 20020401

• Semiochemicals of the Scarabaeinae: VI. Identification of EAD-active constituents of abdominal secretion of male dung beetle, Kheper nigroaeneus.

  Journal of chemical ecology 20020301

• Volatile flavor components of stored nonfat dry milk.

  Journal of agricultural and food chemistry 20020116

• Olfactory cues for oviposition behavior in Toxorhynchites moctezuma and Toxorhynchites amboinensis (Diptera: Culicidae).

  Journal of medical entomology 20020101

• Indole-3-acetic acids and horseradish peroxidase: a new prodrug/enzyme combination for targeted cancer therapy.

  Current pharmaceutical design 20020101

• Chemiluminescence associated with amino acid oxidation mediated by hypochlorous acid.

  Luminescence : the journal of biological and chemical luminescence 20020101

• Relationship between structures of substituted indolic compounds and their degradation by marine anaerobic microorganisms.

  Marine pollution bulletin 20020101

• Molecular modelling of the mouse cytochrome P450 CYP2F2 based on the CYP102 crystal structure template and selective CYP2F2 substrate interactions.

  Drug metabolism and drug interactions 20020101

• Detection of DNA adducts using a quantitative long PCR technique and the fluorogenic 5' nuclease assay (TaqMan).

  Mutation research 20011212

• Association of 3-methyleneindolenine, a toxic metabolite of 3-methylindole, with acute interstitial pneumonia in feedlot cattle.

  American journal of veterinary research 20011001

• Vaccination of boars with a GnRH vaccine (Improvac) eliminates boar taint and increases growth performance.

  Journal of animal science 20011001

• Indolequinone antitumor agents: correlation between quinone structure and rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase. Part 2.

  Journal of medicinal chemistry 20010927

• Identification of mucosal injury in the murine nasal airways by magnetic resonance imaging: site-specific lesions induced by 3-methylindole.

  Toxicology and applied pharmacology 20010815

• Detection and characterization of DNA adducts of 3-methylindole.

  Chemical research in toxicology 20010801

• Selective dehydrogenation/oxygenation of 3-methylindole by cytochrome p450 enzymes.

  Drug metabolism and disposition: the biological fate of chemicals 20010701

• Olfactory marker protein immunohistochemistry and the anterograde transport of horseradish peroxidase as indices of damage to the olfactory epithelium.

  Chemical senses 20010701

• Olfactory memory in the mosquito Culex quinquefasciatus.

  Medical and veterinary entomology 20010601

• Odorants as cell-type specific activators of a heat shock response in the rat olfactory mucosa.

  The Journal of comparative neurology 20010416

• Exciplex-type behavior and partition of 3-substituted indole derivatives in reverse micelles made with benzylhexadecyldimethylammonium chloride, water and benzene.

  Photochemistry and photobiology 20010201

• Synthesis and evaluation of asperlicin analogues as non-peptidal cholecystokinin-antagonists.

  Drug design and discovery 20010101

• [Aerobic methylobacteria are capable of synthesizing auxins].

  Mikrobiologiia 20010101

• Bioactivation of toxicants by cytochrome p450-mediated dehydrogenation mechanisms.

  Advances in experimental medicine and biology 20010101

• Metabolism of 3-methylindole by porcine liver microsomes: responsible cytochrome P450 enzymes.

  Toxicological sciences : an official journal of the Society of Toxicology 20000601

• Attractants for synanthropic flies. Identification of attractants and coattractants for Hippelates eye gnats (Diptera: Chloropidae).

  Journal of agricultural and food chemistry 19760101