Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H6N2 |
Molecular Weight | 82.1038 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CN=CN1
InChI
InChIKey=XLSZMDLNRCVEIJ-UHFFFAOYSA-N
InChI=1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)
4-methylimidazole (4-MEI) is a chemical compound that is not directly added to food; rather it is formed as a byproduct in some foods and beverages during the normal cooking process. For example, 4-MEI may form when coffee beans are roasted and when meats are roasted or grilled. 4-MEI also forms as a trace impurity during the manufacturing of certain types of caramel coloring (known as Class III and Class IV caramel coloring) that are used to color cola-type beverages and other foods. In recent years, evidence for the carcinogenicity of 4-MEI has raised concerns about uses of caramel color type III and IV that may expose consumers to 4-MEI and increase cancer risk.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19730755
Curator's Comment: 4-methylimidazole (4MeI) is a tremorogenic and convulsive agent of concern both in human and veterinary toxicology.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5281 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7835233 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Solvent and pH effects on fast and ultrasensitive 1,1'-oxalyldi(4-methyl)imidazole chemiluminescence. | 2003 Oct |
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Inhibitive properties and surface morphology of a group of heterocyclic diazoles as inhibitors for acidic iron corrosion. | 2005 Dec 20 |
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From model compounds to protein binding: syntheses, characterizations and fluorescence studies of [RuII(bipy)(terpy)L]2+ complexes (bipy = 2,2'-bipyridine; terpy = 2,2':6',2''-terpyridine; L = imidazole, pyrazole and derivatives, cytochrome c). | 2005 Jan 21 |
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Proton transfer from exogenous donors in catalysis by human carbonic anhydrase II. | 2005 May 1 |
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Inhibition of histidine ammonia lyase by heteroaryl-alanines and acrylates. | 2006 May |
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Different protonation equilibria of 4-methylimidazole and acetic acid. | 2007 Dec 3 |
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Toxicology and carcinogenesis studies of 4-methylimidazole (Cas No. 822-36-6) in F344/N rats and B6C3F1 mice (feed studies). | 2007 Jan |
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Toxicity and carcinogenicity studies of 4-methylimidazole in F344/N rats and B6C3F1 mice. | 2008 Jan |
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Two three-dimensional networks in the binary molecular adducts 4-methylimidazolium hydrogen terephthalate and bis(4-methylimidazolium) terephthalate. | 2008 Jun |
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A DFT study of the 67Zn, 14N and 2H electric field gradient tensors in Zinc(II)-4-MeIm complexes and extrapolation to superoxide dismutase. | 2009 Jan |
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Three-dimensional networks in bis(imidazolium) 2,2'-dithiodibenzoate and 4-methylimidazolium 2-[(2-carboxyphenyl)disulfanyl]benzoate. | 2009 Sep |
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A model study of the efficiency of the Asp-His-Ser triad. | 2010 Jul 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15146214
Groups of five male and five female rats and mice were fed diets containing 0, 300, 800, or 2,500 ppm 4-methylimidazole (equivalent to average daily doses of approximately 30, 80, or 220 mg/kg for rats and 65, 170, or 500 mg/kg for mice) for 15 days. In the 4-methylimidazole studies, all animals survived to the end of the studies, and there were no significant differences in mean body weights, clinical findings, organ weights, or gross or microscopic lesions between exposed and control groups. Groups of 10 male and 10 female rats and mice were fed diets containing 0, 625, 1,250, 2,500, 5,000, or 10,000 ppm 2- or 4-methylimidazole (equivalent to average daily doses of approximately 40, 80, 160, 300, or 560 mg/kg 2- or 4-methylimidazole to rats; and 100, 165, 360, 780, or 1,740 mg/kg 2-methylimidazole or 100, 240, 440, 915, or 1,840 mg/kg 4-methylimidazole to male mice; and 90, 190, 400, 800, or 1,860 mg/kg 2-methylimidazole or 110, 240, 540, 1,130, or 3,180 mg/kg 4-methylimidazole to females) for 14 weeks. All animals survived to the end of the 14-week 2-methylimidazole studies. Compared to the controls, the mean body weights were significantly decreased in groups of male rats and mice exposed to 2,500 ppm or greater and in 5,000 and 10,000 ppm female rats and mice.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19730755
Curator's Comment: Mouse Htc-116 cell line was treated with 4-MEI concentrations of 300, 450, 600 and 750 ug/mL for 24 hours and 48 hours periods, after that antiproliferative effect of the 4-MEI was studied by MTT assay. 4-MEI at highest concentration of 24h and at all concentration for 48 h treatment time significantly inhibited cell proliferation when it was compared to control. Also, exposing to the 4-MEI for 48 hours led to a decrease in cells proliferation by concentration dependent manner. https://www.ncbi.nlm.nih.gov/pubmed/28516787
The in vitro effects of 4-methylimidazole (4-MEI) (5 uM-20 mM) on cerebral glutamate decarboxylase (GAD) activity and (in concentrations up to 50 mM) on binding of [(3)H]GABA to cerebral GABA receptors were tested in brain tissue from B6D2 mice. 4MeI in concentrations of 2 mM and above did inhibit GAD activity significantly in vitro, but glutamate and GABA concentrations in mouse brains after lethal 4MeI poisoning were not significantly different from control values. Binding of [(3)H]GABA to cerebral GABA receptors in vitro was significantly inhibited only at 4MeI concentrations of 5 mM and above.
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4-Methylimidazole
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SUBSTANCE RECORD