4-methylimidazole (CHEBI:40035)

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CHEBI:40035 - 4-methylimidazole

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ChEBI Name	4-methylimidazole

ChEBI ID	CHEBI:40035

Definition	Imidazole substituted at position 4 by a methyl group.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB5424070, eMolecules:487834, eMolecules:6871865, ZINC000008283845

Download	Molfile XML SDF

more structures >>

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12 12 0 0 0 0 999 V2000

-0.0030 0.0010 0.6910 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0880 -0.0020 -0.0970 N 0 0 0 0 0 0 0 0 0 0 0 0

1.0860 0.0000 -0.0990 C 0 0 0 0 0 0 0 0 0 0 0 0

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0.6370 0.0000 -1.3920 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.0040 0.0000 2.1980 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3710 0.0020 -2.2020 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1850 -0.0010 -2.1920 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1160 -0.0010 0.2240 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0020 1.0280 2.5620 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8950 -0.5110 2.5610 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8840 -0.5150 2.5610 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 4 0 0 0 0

1 3 4 0 0 0 0

1 6 1 0 0 0 0

2 4 4 0 0 0 0

3 5 4 0 0 0 0

3 9 1 0 0 0 0

4 5 4 0 0 0 0

4 7 1 0 0 0 0

5 8 1 0 0 0 0

6 10 1 0 0 0 0

6 11 1 0 0 0 0

6 12 1 0 0 0 0

M END): 17 ms

reading 12 atoms

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Wikipedia	License
4-Methylimidazole (4-MeI or 4-MEI) is a heterocyclic organic chemical compound with molecular formula H3C–C3H3N2 or C4H6N2. It is formally derived from imidazole through replacement of the hydrogen in position 4 by a methyl group. It is a slightly yellowish solid. 4-MeI may be formed in the browning of certain foods through the Maillard reaction between carbohydrates and amino-containing compounds. In particular, it is found in roasted foods, grilled meats, coffee and in types of caramel coloring produced with ammonia-based processes. It may arise also by fermentation.
Read full article at Wikipedia

Formula

C4H6N2

Net Charge

Average Mass

82.10380

Monoisotopic Mass

82.05310

InChI

InChI=1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)

InChIKey

XLSZMDLNRCVEIJ-UHFFFAOYSA-N

SMILES

Cc1c[nH]cn1

Roles Classification
Chemical Role(s):	reaction intermediate Any chemical substance produced during the conversion of a reactant to a product.

Biological Role(s):	carcinogenic agent A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	4-methylimidazole (CHEBI:40035) has role carcinogenic agent (CHEBI:50903) 4-methylimidazole (CHEBI:40035) has role reaction intermediate (CHEBI:64297) 4-methylimidazole (CHEBI:40035) is a imidazoles (CHEBI:24780)

IUPAC Name

4-methyl-1H-imidazole

Synonyms	Sources
4(5)-methylimidazole	ChEBI
4-Me-i	ChemIDplus
4-MEI	ChEBI
4-METHYLIMIDAZOLE	PDBeChem
4MI	ChEBI

Manual Xrefs	Databases
4-Methylimidazole	Wikipedia
4MZ	PDBeChem
C19262	KEGG COMPOUND
View more database links

Registry Numbers	Types	Sources
1453	Reaxys Registry Number	Reaxys
822-36-6	CAS Registry Number	NIST Chemistry WebBook
822-36-6	CAS Registry Number	ChemIDplus

Citations

Chan PC, Hill GD, Kissling GE, Nyska A (2008)
Toxicity and carcinogenicity studies of 4-methylimidazole in F344/N rats and B6C3F1 mice.
Archives of toxicology 82, 45-53 [PubMed:17619857]
[show Abstract]
4-Methylimidazole (4MI) is used in the manufacture of pharmaceuticals, photographic chemicals, dyes and pigments, cleaning and agricultural chemicals, and rubber. It has been identified as a by-product of fermentation in foods and has been detected in mainstream and side stream tobacco smoke. 4MI was studied because of its high potential for human exposure. Groups of 50 male and 50 female F344/N rats were fed diets containing 0-, 625-, 1,250-, or 2,500 ppm 4MI (males) or 0-, 1,250-, 2,500-, or 5,000 ppm 4MI (females) for 106 weeks. Based on the food consumption the calculated average daily doses were approximately 30, 55, or 115 mg 4MI/kg body weight to males and 60, 120, or 250 mg 4MI/kg to females. Survival of all exposed groups of males and females was similar to that of the control groups. The mean body weights of males in the 1,250- and 2,500 ppm groups and females in the 2,500- and 5,000 ppm groups were less than those of the control groups throughout the study. Feed consumption by 5,000 ppm females was less than that by the controls. Clonic seizures, excitability, hyperactivity, and impaired gait were observed primarily in 2,500- and 5,000 ppm females. The incidence of mononuclear cell leukemia in the 5,000 ppm females was significantly greater than that in the controls. The incidences of hepatic histiocytosis, chronic inflammation, and focal fatty change were significantly increased in all exposed groups of male and female rats. The incidences of hepatocellular eosinophilic and mixed cell foci were significantly increased in 2,500 ppm males and 5,000 ppm females. Groups of 50 male and 50 female B6C3F1 mice were fed diets containing 0-, 312-, 625-, or 1,250 ppm 4MI for 106 weeks. Based on the food consumption the calculated average daily doses were approximately 40, 80, or 170 mg 4MI/kg body weight to males and females. Survival of all exposed groups of males and females was similar to that of the control groups. Mean body weights of males and females in the 1,250 ppm groups and that in the 312- and 625 ppm females were less than those of the control groups. Feed consumption by exposed groups of male and female mice was similar to that by the controls. The incidences of alveolar/bronchiolar adenoma in all exposed groups of females, alveolar/bronchiolar carcinoma in 1,250 ppm males, and alveolar/bronchiolar adenoma or carcinoma (combined) in 1,250 ppm males and 625- and 1,250 ppm females were significantly greater than those in the control groups. The incidence of alveolar epithelial hyperplasia was significantly increased in the 1,250 ppm females. 4MI is carcinogenic inducing alveolar/bronchiolar adenoma and carcinoma in male and female mice. 4MI may also induce mononuclear cell leukemia in female rats.

Karangwa E, Mitchell GE, Tucker RE (1990)
High-performance liquid chromatographic determination of 4-methylimidazole in sheep plasma and in ammoniated tall fescue hay.
Journal of chromatography 532, 105-113 [PubMed:2079523]
[show Abstract]

Chan P, Mahler J, Travlos G, Nyska A, Wenk M (2006)
Induction of thyroid lesions in 14-week toxicity studies of 2 and 4-methylimidazole in Fischer 344/N rats and B6C3F1 mice.
Archives of toxicology 80, 169-180 [PubMed:16180012]
[show Abstract]
Fifteen-day and 14-week studies of 2-methylimidazole (2MI) and 4-methylimidazole (4MI) were conducted because of widespread human exposure via ingestion of food products containing the compounds and lack of toxicity data. Groups of five male and five female Fischer rats and B6C3F1 mice were administered 2MI by dosed feed at 0, 1,200, 3,300, or 10,000 ppm or 4MI at 0, 300, 800, or 2,500 ppm for 15 days, and groups of 10 male and 10 female Fischer rats and B6C3F1 mice were administered 2MI or 4MI at 0, 625, 1,250, 2,500, 5,000 or 10,000 ppm for 14 weeks. In the 15-day studies, 2MI induced thyroid follicular-cell hyperplasia and pituitary pars-distalis hypertrophy in rats and thyroid follicular-cell hypertrophy and spleen hematopoietic-cell proliferation in mice; 4MI induced no histopathological changes in rats and mice. In the 14-week studies, 2MI increased concentrations of thyroid-stimulating hormone (TSH) and decreased those of thyroxine (T(4)) and triiodothyroxine (T(3)) in male and female rats according to the dosage. Incidences of diffuse follicular-cell hyperplasia of the thyroid gland increased significantly in male rats exposed to 1,250 ppm or greater and female rats exposed to 2,500 ppm or greater. Thyroid follicular-cell adenoma was diagnosed in two males in the 10,000-ppm group. A dose-related anemia occurred in female rats. In mice, follicular-cell hypertrophy of the thyroid gland, anemia, splenic hematopoietic-cell proliferation, and hemosiderin in kidney tubules appeared. In rats, 4MI induced tremors and ataxia in the high-dose groups. Serum T(3), T(4), and TSH levels were not altered, and no thyroid lesions occurred. Anemia, hepatocytic vacuolation, testicular degeneration, and prostatic atrophy were observed. In mice, anemia, liver cytoplasmic vacuolization, and renal degeneration and dilation occurred. Our studies demonstrated that, in rats and mice, 2MI induces thyroid hyperplasia and hypertrophy, and both 2MI and 4MI induce anemia; 2MI induces thyroid follicular-cell adenoma in male rats.

Last Modified

04 August 2014

CHEBI:40035 - 4-methylimidazole

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