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

methanimidamide, N,N'-1,2-ethenediyl-

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CAS Number: 288-32-4Picture of molecule3D/inchi
Other(deleted CASRN):116421-26-2
ECHA EINECS - REACH Pre-Reg:206-019-2
Nikkaji Web:J2.566F
Beilstein Number:0103853
XlogP3:-0.10 (est)
Molecular Weight:68.07888000
Formula:C3 H4 N2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:buffering agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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US Patents:Search
EU Patents:Search
Pubchem Patents:Search
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 90.50 °C. @ 760.00 mm Hg
Boiling Point: 257.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.024000 mmHg @ 25.00 °C. (est)
Flash Point: 293.00 °F. TCC ( 145.00 °C. )
logP (o/w): -0.080
Soluble in:
 water, 1.591e+005 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: buffering agents
BOC Sciences
For experimental / research use only.
Imidazole 95%
Odor: characteristic
Use: Imidazole, a highly polar compound, has been used extensively as a corrosion inhibitor and a buffer in the pH range of 6.2-7.8.
Charkit Chemical
Glentham Life Sciences
Imidazole, 99.5%
Glentham Life Sciences
Santa Cruz Biotechnology
For experimental / research use only.
Imidazole ≥99%
For experimental / research use only.
Imidazole ACS reagent, ≥99% (titration)
For experimental / research use only.
Imidazole [for Buffer] >99.0%(GC)(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:
oral-guinea pig LD50 760 mg/kg
Przeglad Epidemiologiczny. Vol. 67, Pg. 295, 1993.

oral-mammal (species unspecified) LD50 1000 mg/kg
Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 608, 1966.

intraperitoneal-mouse LD50 300 mg/kg
National Technical Information Service. Vol. AD277-689

intravenous-mouse LD50 475 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 716, 1983.

oral-mouse LD50 880 mg/kg
German Offenlegungsschrift Patent Document. Vol. #3046325

oral-rat LD50 220 mg/kg
Przeglad Epidemiologiczny. Vol. 67, Pg. 295, 1993.

Dermal Toxicity:
subcutaneous-cat LDLo 125 mg/kg
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 84, Pg. 155, 1918.

subcutaneous-dog LD50 28 mg/kg
Przeglad Epidemiologiczny. Vol. 67, Pg. 295, 1993.

subcutaneous-mouse LD50 817 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 444, 1957.

subcutaneous-rat LD50 626 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 444, 1957.

Inhalation Toxicity:
Not determined
Safety in Use Information:
buffering agents
Recommendation for imidazole usage levels up to:
 not for fragrance use.
Recommendation for imidazole flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):288-32-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :795
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
RTECS:NI3325000 for cas# 288-32-4
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:288-32-4
Pubchem (cid):795
Pubchem (sid):134974460
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
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C01589
HMDB (The Human Metabolome Database):HMDB01525
Export Tariff Code:2933.29.6000
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 spathiphyllum floribundum
Search Trop Picture
 methanimidamide, N,N'-1,2-ethenediyl-


PubMed:Luliconazole for the treatment of fungal infections: an evidence-based review.
PubMed:A novel urea-functionalized surface-confined octadecylimidazolium ionic liquid silica stationary phase for reversed-phase liquid chromatography.
PubMed:Ionic liquid coated magnetic core/shell Fe3O4@SiO2 nanoparticles for the separation/analysis of linuron in food samples.
PubMed:Correction to Synthesis and Application of (13)C-Labeled 2-Acetyl-4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)imidazole (THI), an Immunosuppressant Observed in Caramel Food Colorings.
PubMed:5-Amino-5'-bromo-6-(4-methyl-benzo-yl)-8-nitro-2,3-di-hydro-1H-spiro-[imidazo[1,2-a]pyridine-7,3'-indolin]-2'-one including an unknown solvate.
PubMed:Chronic activation of central AMPK attenuates glucose-stimulated insulin secretion and exacerbates hepatic insulin resistance in diabetic rats.
PubMed:Determination of caramel colorants' by-products in liquid foods by ultra-high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS).
PubMed:[Determination of major metal cations in juices and nectars by capillary zone electrophoresis].
PubMed:Isolation, identification and structure elucidation of two novel process-related impurities of retigabine.
PubMed:Crystallization and preliminary crystallographic analysis of histamine dehydrogenase from Natrinema gari BCC 24369.
PubMed:Anxiolytic and antidepressant-like activities of the novel and potent non-imidazole histamine H₃ receptor antagonist ST-1283.
PubMed:Determination of preservatives in soft drinks by capillary electrophoresis with ionic liquids as the electrolyte additives.
PubMed:Inhibition of human pyridoxal kinase by 2-acetyl-4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)imidazole (THI).
PubMed:Sensitized chemiluminescence of 2-phenyl-4,5-di(2-furyl)-1H-imidazole/K₃Fe(CN)₆/propyl gallate system combining with solid-phase extraction for the determination of propyl gallate in edible oil.
PubMed:Prospective therapeutic agents for obesity: molecular modification approaches of centrally and peripherally acting selective cannabinoid 1 receptor antagonists.
PubMed:An AIL/IL-based liquid/liquid extraction system for the purification of His-tagged proteins.
PubMed:Chickpea chelating peptides inhibit copper-mediated lipid peroxidation.
PubMed:New insights into the mechanism of neurolathyrism: L-β-ODAP triggers [Ca2+]i accumulation and cell death in primary motor neurons through transient receptor potential channels and metabotropic glutamate receptors.
PubMed:Determination of 4-Methylimidazole and 2-Acetyl-4()- tetrahydroxybutylimidazole in Caramel Color and Processed Foods by LC-MS/MS.
PubMed:Pharmacokinetic profiles of the novel COX-2 selective inhibitor cimicoxib in dogs.
PubMed:Tuning chelation by the surfactant-like peptide A6H using predetermined pH values.
PubMed:Development of a novel biosensor based on a conducting polymer.
PubMed:Candidiasis (oropharyngeal).
PubMed:The mechanism of copper uptake by tyrosinase from Bacillus megaterium.
PubMed:Oriented immobilization of His-tagged protein on a redox active thiol derivative of DPTA-Cu(II) layer deposited on a gold electrode--the base of electrochemical biosensors.
PubMed:2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) induces microglial nitric oxide production and subsequent rat primary cortical neuron apoptosis through p38/JNK MAPK pathway.
PubMed:Formation and ecotoxicity of N-heterocyclic compounds on ammoxidation of mono- and polysaccharides.
PubMed:Purification, crystallization and preliminary crystallographic analysis of soybean mature glycinin A1bB2.
PubMed:Cycloxaprid insecticide: nicotinic acetylcholine receptor binding site and metabolism.
PubMed:Synthesis and application of (13)C-labeled 2-acetyl-4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)imidazole (THI), an immunosuppressant observed in caramel food colorings.
PubMed:An improved GC-MS method in determining glycerol in different types of biological samples.
PubMed:Azole fungicides disturb intracellular Ca2+ in an additive manner in dopaminergic PC12 cells.
PubMed:Development of a fast and selective separation method to determine histamine in tuna fish samples using capillary zone electrophoresis.
PubMed:Croton lechleri Müll. Arg. (Euphorbiaceae) stem bark essential oil as possible mutagen-protective food ingredient against heterocyclic amines from cooked food.
PubMed:Diaqua-bis-(1H-imidazole-4-carboxyl-ato-κ(2) N (3),O (4))manganese(II).
PubMed:Structures and reaction mechanisms of GTP cyclohydrolases.
PubMed:Molecular characterization, fitness and mycotoxin production of benzimidazole-resistant isolates of Penicillium expansum.
PubMed:L-carnosine modulates respiratory burst and reactive oxygen species production in neutrophil biochemistry and function: may oral dosage form of non-hydrolized dipeptide L-carnosine complement anti-infective anti-influenza flu treatment, prevention and self-care as an alternative to the conventional vaccination?
PubMed:Synthesis, fungicidal activity, and sterol 14α-demethylase binding interaction of 2-azolyl-3,4-dihydroquinazolines on Penicillium digitatum.
PubMed:Casein maps: effect of ethanol, pH, temperature, and CaCl2 on the particle size of reconstituted casein micelles.
PubMed:Determination of 2-methylimidazole, 4-methylimidazole and 2-acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole in caramel colours and cola using LC/MS/MS.
PubMed:Triflumizole is an obesogen in mice that acts through peroxisome proliferator activated receptor gamma (PPARγ).
PubMed:Fast determination of cations in honey by capillary electrophoresis: a possible method for geographic origin discrimination.
PubMed:Site E14 in hemoglobins and myoglobins: a key residue that affects hemin loss and lipid oxidation capacity.
PubMed:Strongly Phosphorescent Iridium(III)-Porphyrins - New Oxygen Indicators with Tuneable Photophysical Properties and Functionalities.
PubMed:Comparison of indirect and direct quantification of esters of monochloropropanediol in vegetable oil.
PubMed:Intracerebroventricular administration of metformin inhibits ghrelin-induced Hypothalamic AMP-kinase signalling and food intake.
PubMed:Molecular dynamics simulations of the interaction of glucose with imidazole in aqueous solution.
PubMed:Simultaneous quantitation of 2-acetyl-4-tetrahydroxybutylimidazole, 2- and 4-methylimidazoles, and 5-hydroxymethylfurfural in beverages by ultrahigh-performance liquid chromatography-tandem mass spectrometry.
PubMed:Weakly hydrated surfaces and the binding interactions of small biological solutes.
PubMed:Pharmacokinetic optimization of 4-substituted methoxybenzoyl-aryl-thiazole and 2-aryl-4-benzoyl-imidazole for improving oral bioavailability.
PubMed:Validation study on avermectine residues in foodstuffs.
PubMed:Use of ionic liquid aggregates of 1-hexadecyl-3-butyl imidazolium bromide in a focused-microwave assisted extraction method followed by high-performance liquid chromatography with ultraviolet and fluorescence detection to determine the 15+1 EU priority PAHs in toasted cereals ("gofios").
PubMed:Requirement for store-operated calcium entry in sodium butyrate-induced apoptosis in human colon cancer cells.
PubMed:Cell wall polysaccharides of near-isogenic lines of melon (Cucumis melo L.) and their inbred parentals which show differential flesh firmness or physiological behavior.
PubMed:Neuropeptide S receptor: recent updates on nonpeptide antagonist discovery.
PubMed:[Adsorption performances for sulfur dioxide using imidazole ionic liquids].
PubMed:Effects of cooking variables on formation of heterocyclic amines (HCA) in roasted pork and mackerel.
PubMed:Metabolic alterations in different developmental stages of Pilocarpus microphyllus.
PubMed:Plant-growth regulator, imidazole-4-carboxamide, produced by the fairy ring forming fungus Lepista sordida.
PubMed:Histaminol: identification and HPLC analysis of a novel compound in wine.
PubMed:Increased intestinal absorption of mizoribine, an immunosuppressive agent, in cholestatic rats.
PubMed:Effects of nitric oxide synthase inhibitors 1-(2-trifluoromethylphenyl)--imidazole (TRIM) and 7-nitroindazole (7-NI) on learning and memory in mice.
PubMed:Analysis and chemistry of migrants from wine fining polymers.
PubMed:Protective effect of sulforaphane on human vascular endothelial cells against lipopolysaccharide-induced inflammatory damage.
PubMed:Detection and quantification of maitotoxin-like compounds using a neuroblastoma (Neuro-2a) cell based assay. Application to the screening of maitotoxin-like compounds in Gambierdiscus spp.
PubMed:Cloning, expression, and characterization of a thioredoxin reductase cDNA from Taiwanofungus camphorata.
PubMed:Synthesis and SAR of derivatives based on 2-biarylethylimidazole as bombesin receptor subtype-3 (BRS-3) agonists for the treatment of obesity.
PubMed:Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities.
PubMed:Histamine modified 2'-deoxyriboadenosine--potential copper binding site in DNAzymes.
PubMed:Chelating Langmuir-Blodgett film: a new versatile chemiluminescent sensing layer for biosensor applications.
PubMed:Protonation-dissociation reactions of imazamethabenz-methyl and imazamethabenz-Acid in relation to their soil sorption and abiotic degradation.
PubMed:Cloning, expression, and characterization of an enzyme possessing both glutaredoxin and dehydroascorbate reductase activity from Taiwanofungus camphorata.
PubMed:Carbon nanotubes activate blood platelets by inducing extracellular Ca2+ influx sensitive to calcium entry inhibitors.
PubMed:Role of Nrf2 in prevention of high-fat diet-induced obesity by synthetic triterpenoid CDDO-imidazolide.
PubMed:Bioisosteric replacement of the hydrazide pharmacophore of the cannabinoid-1 receptor antagonist SR141716A. Part I: potent, orally-active 1,4-disubstituted imidazoles.
PubMed:Use of ultra-high-pressure liquid chromatography-quadrupole time-of-flight MS to discover the presence of pesticide metabolites in food samples.
PubMed:Construction of a full-length cDNA Library from Chinese oak silkworm pupa and identification of a KK-42-binding protein gene in relation to pupa-diapause termination.
PubMed:Light-induced oxidation of tryptophan and histidine. Reactivity of aromatic N-heterocycles toward triplet-excited flavins.
PubMed:Cloning, expression, and purification of a functional glutathione reductase from sweet potato (Ipomoea batatas [L.] Lam): kinetic studies and characterization.
PubMed:Analysis of aliphatic amines using head-column field-enhanced sample stacking in MEKC with LIF detection.
PubMed:CYP1A1 induction and CYP3A4 inhibition by the fungicide imazalil in the human intestinal Caco-2 cells-comparison with other conazole pesticides.
PubMed:Diarylimidazolyl oxadiazole and thiadiazole derivatives as cannabinoid CB1 receptor antagonists.
PubMed:Arachidonic acid increases antifungal susceptibility of Candida albicans and Candida dubliniensis.
PubMed:[Identification of catalytically active groups of wheat (Triticum aestivum L.) germ lipase].
PubMed:Efficient production and partial characterization of aspartyl aminopeptidase from Aspergillus oryzae.
PubMed:Characterization and distribution of phenolics in carrot cell walls.
PubMed:Isolation and characterization of superoxide dismutase from wheat seedlings.
PubMed:Comprehensive management of patients with superficial fungal infections: the role of sertaconazole nitrate.
PubMed:2-Substituted piperazine-derived imidazole carboxamides as potent and selective CCK1R agonists for the treatment of obesity.
PubMed:Discovery of imidazole carboxamides as potent and selective CCK1R agonists.
PubMed:Stabilization of thin-layer agarose gels after isoelectric focusing with polyacrylamide enables reverse imidazole-zinc staining and facilitates two-dimensional gel electrophoresis.
PubMed:Heart-cutting two-dimensional liquid chromatography methods for quantification of 2-acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole in Class III caramel colours.
PubMed:Lycopene production using Blakeslea trispora in the presence of 2-methyl imidazole: yield, selectivity, and safety aspects.
PubMed:Dehydroascorbate reductase cDNA from sweet potato (Ipomoea batatas [L.] Lam): expression, enzyme properties, and kinetic studies.
PubMed:Diffusing wave spectroscopy study of the colloidal interactions occurring between casein micelles and emulsion droplets: comparison to hard-sphere behavior.
PubMed:Preparation of unglycosylated human caseinomacropeptide by engineering DAB Escherichia coli.
PubMed:Anserine and carnosine determination in meat samples by pure micellar liquid chromatography.
PubMed:Characterization of a novel and selective cannabinoid CB1 receptor inverse agonist, Imidazole 24b, in rodents.
PubMed:Anti-clastogenic effect of magnolol on benzo(a)pyrene-induced clastogenicity in mice.
PubMed:Photolysis pathway of imazapic in aqueous solution: ultrahigh resolution mass spectrometry analysis of intermediates.
PubMed:Use of metabolic stimulators and inhibitors for enhanced production of beta-carotene and lycopene by Blakeslea trispora NRRL 2895 and 2896.
PubMed:Application of a monoclonal-based immunoassay for the determination of imazalil in fruit juices.
PubMed:Activation of p38/MEF2C pathway by all-trans retinoic acid in cardiac myoblasts.
PubMed:In situ measurements of pH changes in beta-lactoglobulin solutions under high hydrostatic pressure.
PubMed:Monensin causes transient calcium ion influx into mouse splenic lymphocytes in a sodium ion-independent fashion.
PubMed:[Determination of 3-monochloropropane-1,2-diol in hydrolyzed vegetable proteins and soy by solid phase extraction and gas chromatography/negative chemical ionization-mass spectrometry].
PubMed:{mu-N,N'-Bis[3-(dimethylamino)propyl]oxamidato(2-)-kappa(6)N,N',O':N'',N''',O}bis[(1H-imidazole-kappaN3)(methanol-kappaO)copper(II)] bis(perchlorate).
PubMed:Supercritical fluid extraction (SFE) of 4(5)-methylimidazole (4-MeI) and 2-acetyl-4(5)-(1,2,3,4)-tetrahydroxybutyl-imidazole (THI) from ground-coffee with high-performance liquid chromatographic-electrospray mass spectrometric quantification (HPLC/ESI-MS).
PubMed:Evidence for tolerance following repeated dosing in rats with ciproxifan, but not with A-304121.
PubMed:When quinones meet amino acids: chemical, physical and biological consequences.
PubMed:Solid-phase extraction of 4(5)-methylimidazole (4MeI) and 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)-imidazole (THI) from foods and beverages with subsequent liquid chromatographic-electrospray mass spectrometric quantification.
PubMed:Genotoxic and aneugenic properties of an imidazole derivative.
PubMed:Prochloraz: an imidazole fungicide with multiple mechanisms of action.
PubMed:Peripheral administration of a melanocortin 4-receptor inverse agonist prevents loss of lean body mass in tumor-bearing mice.
PubMed:Cannabinoid-mediated elevation of intracellular calcium: a structure-activity relationship.
PubMed:A review of the structural and functional features of olmesartan medoxomil, an angiotensin receptor blocker.
PubMed:Preparation and properties of an immobilized pectinlyase for the treatment of fruit juices.
PubMed:Validation of a histamine H3 receptor model through structure-activity relationships for classical H3 antagonists.
PubMed:Biochemical characterization of a cambialistic superoxide dismutase isozyme from diatom Thallassiosira weissflogii: cloning, expression, and enzyme stability.
PubMed:Sertaconazole: updated review of a topical antifungal agent.
PubMed:A competitive ELISA detecting 7-methylguanosine adduct induced by N-nitrosodimethylamine exposure.
PubMed:Assessment of pharmacology and potential anti-obesity properties of H3 receptor antagonists/inverse agonists.
PubMed:Trans- and cis-resveratrol increase cytoplasmic calcium levels in A7r5 vascular smooth muscle cells.
PubMed:Characterization of Fe/Mn-superoxide dismutase from diatom Thallassiosira weissflogii: cloning, expression, and property.
PubMed:Antigenotoxic properties of Cassia tea (Cassia tora L.): mechanism of action and the influence of roasting process.
PubMed:Inhibition of mutagenicity of food-derived heterocyclic amines by sulforaphane--a constituent of broccoli.
PubMed:Artificial neural networks for prediction of antibacterial activity in series of imidazole derivatives.
PubMed:Stabilization of oil-in-water emulsions by cod protein extracts.
PubMed:Molecular complexes of IQ and 4-hydroxy-coumarin: a mutagen-anti-mutagen system.
PubMed:Design, synthesis, and biological evaluation of substituted 2-cyclohexyl-4-phenyl-1H-imidazoles: potent and selective neuropeptide Y Y5-receptor antagonists.
PubMed:Inhibitory effects of beer on heterocyclic amine-induced mutagenesis and PhIP-induced aberrant crypt foci in rat colon.
PubMed:Antiobesity effects of A-331440, a novel non-imidazole histamine H3 receptor antagonist.
PubMed:Identification of 2-[2-[2-(5-bromo-2- methoxyphenyl)-ethyl]-3-fluorophenyl]-4,5-dihydro-1H-imidazole (ML00253764), a small molecule melanocortin 4 receptor antagonist that effectively reduces tumor-induced weight loss in a mouse model.
PubMed:Anatomy and cell wall polysaccharides of almond (Prunus dulcis D. A. Webb) seeds.
PubMed:Early and late apoptosis events in human transformed and non-transformed colonocytes are independent on intracellular acidification.
PubMed:AMP-activated protein kinase plays a role in the control of food intake.
PubMed:Production and characterization of oil-in-water emulsions containing droplets stabilized by beta-lactoglobulin-pectin membranes.
PubMed:Inhibitory effect of dibenzoylmethane on mutagenicity of food-derived heterocyclic amine mutagens.
PubMed:Inhibitory effect of curcumin and its natural analogues on genotoxicity of heterocyclic amines from cooked food.
PubMed:Polymerization and calcium binding of the tubulin-colchicine complex in the GDP state.
PubMed:Inhibitory effects of (-)-epigallocatechin gallate on the mutation, DNA strand cleavage, and DNA adduct formation by heterocyclic amines.
PubMed:Neutralization of toxic heme by Plasmodium falciparum histidine-rich protein 2.
PubMed:Utilization of Folin-Ciocalteu phenol reagent for the detection of certain nitrogen compounds.
PubMed:Activation of p38 mitogen-activated protein kinase and activator protein-1 during the promotion of neurite extension of PC-12 cells by 15-deoxy-delta12,14-prostaglandin J2.
PubMed:A His-tag based immobilization method for the preparation and reconstitution of apoflavoproteins.
PubMed:Mobility and degradation of the herbicide imazosulfuron in lysimeters under field conditions.
PubMed:Copper/zinc-superoxide dismutase from lemon cDNA and enzyme stability.
PubMed:Antiandrogenic effects in vitro and in vivo of the fungicide prochloraz.
PubMed:Reactivity and selectivity of the N-acetyl-Glu-P-1, N-acetyl-Glu-P-2, N-acetyl-MeIQx, and N-acetyl-IQx nitrenium ions: comparison to carbocyclic N-arylnitrenium ions.
PubMed:Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH(2) at the mouse melanocortin receptors. 1. Modifications at the His position.
PubMed:Characterization of copper/zinc-superoxide dismutase from Pagrus major cDNA and enzyme stability.
PubMed:Binding activity of natto (a fermented food) and Bacillus natto isolates to mutagenic-carcinogenic heterocyclic amines.
PubMed:Identification of the major metabolites of prochloraz in rainbow trout by liquid chromatography and tandem mass spectrometry.
PubMed:Olive fruit cell wall: degradation of pectic polysaccharides during ripening.
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:Action against Vibrio cholerae O1 Tox+ of chemical products used in the lemon production.
PubMed:Histamine fish poisoning revisited.
PubMed:Dynamic rheology of renneted milk gels containing fat globules stabilized with different surfactants.
PubMed:Hyperphagic effect of novel compounds with high affinity for imidazoline I(2) binding sites.
PubMed:Orthokinetic flocculation of caseinate-stabilized emulsions: influence of calcium concentration, shear rate, and protein content.
PubMed:Characterization of the dimer-monomer equilibrium of the papaya Copper/Zinc superoxide dismutase and its equilibrium shift by a single amino acid mutation.
PubMed:Sorption behavior of prochloraz in different soils.
PubMed:Phenolics: blocking agents for heterocyclic amine-induced carcinogenesis.
PubMed:Effects of roselle (Hibiscus sabdariffa Linn.), a Thai medicinal plant, on the mutagenicity of various known mutagens in Salmonella typhimurium and on formation of aberrant crypt foci induced by the colon carcinogens azoxymethane and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in F344 rats.
PubMed:Antimutagenic effects and possible mechanisms of action of vitamins and related compounds against genotoxic heterocyclic amines from cooked food.
PubMed:Enzymatic formation of G-group aflatoxins and biosynthetic relationship between G- and B-group aflatoxins.
PubMed:The "prescription-to-OTC switch" movement. Its effects on antifungal vaginitis preparations.
PubMed:Mizoribine and mycophenolate mofetil.
PubMed:Alcohol-histamine interactions.
PubMed:Capillary electrophoretic method for quality control of phospholipid products.
PubMed:Scavenging effect of various tea extracts on superoxide derived from the metabolism of mutagens.
PubMed:Nitro-imidazole radiosensitizer-induced toxicity in cynomolgus monkeys.
PubMed:Degradation of pectic polysaccharides in pickled green olives.
PubMed:Effect of some cooked food mutagens on unscheduled DNA synthesis in cultured precision-cut rat, mouse and human liver slices.
PubMed:Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole.
PubMed:Assessment of the protein quality of the smooth muscle myofibrillar and connective tissue proteins of chicken gizzard.
PubMed:Comparison of the effects of the antimetastatic compound ImH[trans-RuCl4(DMSO)Im] (NAMI-A) on the arthritic rat and on MCa mammary carcinoma in mice.
PubMed:Binding of heterocyclic amines by lactic acid bacteria from miso, a fermented Japanese food.
PubMed:The immunomodulatory compound 2-acetyl-4-tetrahydroxybutyl imidazole causes sequestration of lymphocytes in non-lymphoid tissues.
PubMed:Polar and non-polar heterocyclic amines in cooked fish and meat products and their corresponding pan residues.
PubMed:Enhancement of hepatocarcinogenesis by combined administration of food-derived heterocyclic amines at low doses in the rat.
PubMed:Antimutagenic effect of methanolic extracts from peanut hulls.
PubMed:Determination of heterocyclic amines in flame-grilled fish patty by capillary electrophoresis.
PubMed:Diagnosis and treatment of tinea versicolor.
PubMed:Rare activation of the human c-Ha-ras transgene of mice in hemangioendothelial sarcomas and liver tumors induced by Glu-P-1.
PubMed:Comparison of crystal structure and theory for 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
PubMed:Oxidation of caffeine and related methylxanthines in ascorbate and polyphenol-driven Fenton-type oxidations.
PubMed:Relationship between antimutagenic activity and major components of various teas.
PubMed:The immunosuppressive compound 2-acetyl-4-tetrahydroxybutyl imidazole inhibits the allogeneic mixed lymphocyte reaction by sequestration of a recirculating subpopulation of T cells.
PubMed:The SCID-hu mouse as a tool in immunotoxicological risk assessment: effects of 2-acetyl-4(5)-tetrahydroxybutyl-imidazole (THI) and di-n-butyltin dichloride (DBTC) on the human thymus in SCID-hu mice.
PubMed:Visoltricin, a novel biologically active compound produced by Fusarium tricinctum.
PubMed:Pyridoxine supplementation protects mice from suppression of contact hypersensitivity induced by 2-acetyl-4-tetrahydroxybutylimidazole (THI), ultraviolet B radiation (280-320 nm), or cis-urocanic acid.
PubMed:Genetic alterations in HCA-induced tumors.
PubMed:Carcinogens in foods: heterocyclic amines and cancer and heart disease.
PubMed:Effect of high fat diet on liver microsomal oxygenations in ferret.
PubMed:The photochemical properties of fluoroaluminum phthalocyanine.
PubMed:Binding properties of lactic acid bacteria from 'Idly' towards food-borne mutagens.
PubMed:Comparison of various immunochemical assays for the detection of ethylene oxide-DNA adducts with monoclonal antibodies against imidazole ring-opened N7-(2-hydroxyethyl)guanosine: application in a biological monitoring study.
PubMed:Immunotoxicity of the colour additive caramel colour III; a review on complicated issues in the safety evaluation of a food additive.
PubMed:Site-specific oxidation of histidine residues in glycated insulin mediated by Cu2+.
PubMed:Glucuronidation of N-hydroxy heterocyclic amines by human and rat liver microsomes.
PubMed:Evaluation of the antimutagenic potential of anthracene: in vitro and ex vivo studies.
PubMed:Immobilized metal ion affinity chromatography.
PubMed:Histidine 21 does not play a major role in diphtheria toxin catalysis.
PubMed:Perturbing the metal site in D-xylose isomerase. Effect of mutations of His-220 on enzyme stability.
PubMed:Effects of subchronic exposure to Caramel Colour III on the immune system in mice.
PubMed:Mutation spectra of Glu-P-1 in Salmonella: induction of hotspot frameshifts and site-specific base substitutions.
PubMed:Heterocyclic aromatic amine content of selected beef flavors.
PubMed:An active-site peptide containing the second essential carboxyl group of dextransucrase from Leuconostoc mesenteroides by chemical modifications.
PubMed:Hemoglobin denaturation and iron release in acidified red blood cell lysate--a possible source of iron for intraerythrocytic malaria parasites.
PubMed:The direct glucuronidation of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) by human and rabbit liver microsomes.
PubMed:Carcinogenic factors in food with relevance to colon cancer development.
PubMed:Econazole inhibits thapsigargin-induced platelet calcium influx by mechanisms other than cytochrome P-450 inhibition.
PubMed:Expression and mutation of soybean beta-amylase in Escherichia coli.
PubMed:Immunotoxic effects of the color additive caramel color III: immune function studies in rats.
PubMed:Effects of the colour additive caramel colour III on the immune system: a study with human volunteers.
PubMed:Effects of 2-acetyl-4-tetrahydroxybutyl imidazole (THI) on the thymus of rats.
PubMed:Selective oxidation of histidine residues in proteins or peptides through the copper(II)-catalysed autoxidation of glucosone.
PubMed:Metabolism of an imidazole fungicide (prochloraz) in the rat after oral administration.
PubMed:Automation of a clean-up procedure for determination of trichothecenes in cereals using a charcoal-alumina column.
PubMed:Prevention of spontaneous and cyclophosphamide-induced diabetes in non-obese diabetic (NOD) mice with oral 2-acetyl-4-tetrahydroxybutylimidazole (THI), a component of caramel colouring III.
PubMed:Effects of Caramel Colour III on the number of blood lymphocytes: a human study on Caramel Colour III immunotoxicity and a comparison of the results with data from rat studies.
PubMed:Suppression of genotoxicity of carcinogens by (-)-epigallocatechin gallate.
PubMed:The role of lymphocyte production and migration in the lymphopenia caused by 2-acetyl-4-tetrahydroxybutyl imidazole.
PubMed:Enhancement of the mutagenicity of IQ and MeIQ by nitrite in the Salmonella system.
PubMed:Comparative carcinogenicity of 4-aminobiphenyl and the food pyrolysates, Glu-P-1, IQ, PhIP, and MeIQx in the neonatal B6C3F1 male mouse.
PubMed:Effects of the color additive caramel color III and 2-acetyl-4(5)-tetrahydroxybutylimidazole (THI) on the immune system of rats.
PubMed:Quantitation of mutagenic/carcinogenic heterocyclic aromatic amines in food products.
PubMed:Influence of histidine on lipid peroxidation in sarcoplasmic reticulum.
PubMed:Antimutagenic effect of Maillard browning products obtained from amino acids and sugars.
PubMed:The involvement of the sympathetic nervous system in meal-induced thermogenesis in mice.
PubMed:Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon.
PubMed:Immunosuppressive effects of 2-acetyl-4-tetrahydroxybutyl imidazole (THI) in the rat.
PubMed:In vitro effects of an imidazole antifungal, prochloraz, on spectral and catalytic properties of microsomal cytochromes P-450.
PubMed:Numerical method to analyze pH-profile from initial velocity data and semi-empirical procedure to identify catalytic residues of enzymes using pK and heat of ionization.
PubMed:The formation of heart DNA adducts in F344 rat following dietary administration of heterocyclic amines.
PubMed:Characteristics of the interaction of calcium with casein submicelles as determined by analytical affinity chromatography.
PubMed:Site-specific oxidation of angiotensin I by copper(II) and L-ascorbate: conversion of histidine residues to 2-imidazolones.
PubMed:The in vivo and in vitro activity of AHR-13268D, a new antiallergic/antihistaminic agent.
PubMed:Antimutagenicity and binding of lactic acid bacteria from a Chinese cheese to mutagenic pyrolyzates.
PubMed:Simple methods for quantifying mutagenic heterocyclic aromatic amines in food products.
PubMed:15N nuclear magnetic resonance studies on the tautomerism of 8-hydroxy-2'-deoxyguanosine, 8-hydroxyguanosine, and other C8-substituted guanine nucleosides.
PubMed:Highly site-specific oxygenation of 1-methylhistidine and its analogue with a copper (II)/ascorbate-dependent redox system.
PubMed:Occurrence of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole (Glu-P-1) and other heterocyclic amine mutagens in oil of charred egg yolk (ranyu).
PubMed:Characterization of pH-dependent conformational heterogeneity in Rhodospirillum rubrum cytochrome c2 using 15N and 1H NMR.
PubMed:Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA 1535/pSK1002.
PubMed:Benzanthrone: a new substrate for hepatic microsomal cytochrome P-450.
PubMed:Monooxygenation of N-acetylhistamine mediated by L-ascorbate.
PubMed:Preferential induction of the rat hepatic P450 I proteins by the food carcinogen 2-amino-3-methyl-imidazo[4,5-f]quinoline.
PubMed:Effects of lysosomotropic detergents on the human malarial parasite Plasmodium falciparum in in vitro culture.
PubMed:Metabolic activation of chemical carcinogens by hepatic preparations from streptozotocin-treated rats.
PubMed:Induction of rat hepatic cytochrome P-450 I proteins by the antimutagen anthraflavic acid.
PubMed:Role of advanced glycosylation products in complications of diabetes.
PubMed:Thromboxane synthesis inhibitors and postprandial jejunal capillary exchange capacity.
PubMed:Synthesis and mutagenic activity of nitro-imidazoarenes. A study on the mechanism of the genotoxicity of heterocyclic arylamines and nitroarenes.
PubMed:Species and sex differences in genotoxicity of heterocyclic amine pyrolysis and cooking products in the hepatocyte primary culture/DNA repair test using rat, mouse, and hamster hepatocytes.
PubMed:Evaluation of antagonists of the discriminative stimulus and response rate effects of phencyclidine.
PubMed:Clinical pharmacokinetics of ketoconazole.
PubMed:Detection of carcinogenic glutamic acid pyrolysis products in Worcestershire sauce by high-performance liquid chromatography.
PubMed:Initiating activity in a two-stage mouse skin model of nine mutagenic pyrolysates of amino acids, soybean globulin and proteinaceous food.
PubMed:Prostaglandin H synthase-dependent mutagenic activation of heterocyclic aromatic amines of the IQ-type.
PubMed:A note on the nature of the haematin pigments present in freeze dried and cooked beef.
PubMed:Metal protein interactions.
PubMed:[Th role of human intestinal flora on the metabolic activation of pyrolysis products].
PubMed:Etiology of ammoniated hay toxicosis.
PubMed:Carcinogenicity in mice and rats of heterocyclic amines in cooked foods.
PubMed:Mutagenic activities of heterocyclic amines in Chinese hamster lung cells in culture.
PubMed:Metabolic aspects of pyrolysis mutagens in food.
PubMed:Structure-activity relationships of nitro and methyl-nitro derivatives of indoline, indole, indazole and benzimidazole in Salmonella typhimurium.
PubMed:Thromboxane synthesis inhibition and postprandial intestinal hyperemia and oxygenation.
PubMed:Enhancement of hepatocellular genotoxicity of several mutagens from amino acid pyrolysates and broiled foods following ethanol pretreatment.
PubMed:Effect of food intake on urinary excretions of histamine, N tau-methylhistamine, imidazole acetic acid and its conjugate(s) in humans and mice.
PubMed:Pharmacologic review: a review of the literature of ketoconazole therapy in the treatment of tinea pedis and onychomycosis.
PubMed:Induction of cancers in the intestine, liver and various other organs of rats by feeding mutagens from glutamic acid pyrolysate.
PubMed:Biochemical effects of some derivatives of dipyrido[1,2-a:3,'2'-d]imidazole related to protein pyrolysates on rat liver microsomes.
PubMed:Possible genotoxic carcinogens in foods in relation to cancer causation.
PubMed:Metabolic profile of caecal micro-organisms from rats fed indigestible plant cell-wall components.
PubMed:Formation of mutagens in boiled pork extract.
PubMed:A modification of imazalil residue analysis in treated grapefruit.
PubMed:[Blockade of nitrogen oxide and nitrites by various substances].
PubMed:[Effect of biologically active agents on the feeding response of Dileptus anser].
PubMed:Reactions between peroxidizing lipids and histidyl residue analogues: enhancement of lipid oxidation and browning by 4-methylimidazole.
PubMed:Qualitative tests for added coloring matter in meat products.
PubMed:Calcium-activated tension of skinned muscle fibers of the frog. Dependence on magnesium adenosine triphosphate concentration.
Isol. from the seeds of Lens culinaris (lentil). Also present in the seeds of other legumes: Macrotyloma uniflorum (horse gram), Psophocarpus tetragonolobus (winged bean), Vigna radiata (mung bean) Imidazole is a 5-membered planar ring, which is soluble in water and other polar solvents. It exists in two equivalent tautomeric forms because the hydrogen atom can be located on either of the two nitrogen atoms. Imidazole is a highly polar compound, as evidenced by a calculated dipole of 3.61D, and is entirely soluble in water. The compound is classified as aromatic due to the presence of a sextet of ?-electrons, consisting of a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring.; Imidazole is a heterocyclic aromatic organic compound. It is further classified as an alkaloid. Imidazole refers to the parent compound C3H4N2, while imidazoles are a class of heterocycles with similar ring structure but varying substituents. This ring system is present in important biological building blocks such as histidine and histamine. Imidazole can act as a base and as a weak acid. Imidazole exists in two tautomeric forms with the hydrogen atom moving between the two nitrogens. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole. Imidazole is a 5 membered planar ring which is soluble in water and polar solvents. Imidazole is a base and an excellent nucleophile. It reacts at the NH nitrogen, attacking alkylating and acylating compounds. It is not particularly susceptible to electrophilic attacks at the carbon atoms, and most of these reactions are substitutions that keep the aromaticity intact. One can see from the resonance structure that the carbon-2 is the carbon most likely to have a nucleophile attack it, but in general nucleophilic substitutions are difficult with imidazole. Imidazole is incorporated into many important biological molecules. The most obvious is the amino acid histidine, which has an imidazole side chain. histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin.; Imidazole is an organic compound with the formula C3H4N2. This aromatic heterocyclic is classified as an alkaloid. Imidazole refers to the parent compound whereas imidazoles are a class of heterocycles with similar ring structure but varying substituents. This ring system is present in important biological building blocks such as histidine, and the related hormone histamine. Imidazole can serve as a base and as a weak acid. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole.; Imidazole is incorporated into many important biological molecules. The most pervasive is the amino acid histidine, which has an imidazole side chain. Histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin. Histidine can be decarboxylated to histamine, which is also a common biological compound. It is a component of the toxin that causes urticaria, which is another name for allergic hives. The relationship between histidine and histamine are shown below:; This is a general method which is able to give good yields for substituted imidazoles. It is essentially an adaptation of the Debus method called the Debus-Radziszewski imidazole synthesis. The starting materials are substituted glyoxal, aldehyde, amine, and ammonia or an ammonium salt.
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