2-Methylimidazole is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

that is structurally related to

imidazole Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole. Many natural products, ...

with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

CH₃C₃H₂N₂H. It is a white or colorless solid that is highly soluble in polar organic solvents and water. It is a precursor to a range of drugs and is a ligand in

coordination chemistry A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

Synthesis and reactions

It is prepared by condensation of

glyoxal Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

and

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic compound, organic chemical compound with the chemical formula, formula , sometimes abbreviated as . It is a colorless liquid or gas, boiling near room temperature. It is one of the most ...

, a Radziszewski reaction.

Nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...

gives 5-nitro derivative.Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. "Imidazole and Derivatives." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, 2-Methylimidazole is a sterically hindered imidazole that is used to simulate the coordination of histidine to heme complexes. It can be deprotonated to make imidazolate-based

coordination polymer Coordination may refer to: * Coordination (linguistics), a compound grammatical construction * Coordination complex, consisting of a central atom or ion and a surrounding array of bound molecules or ions ** A chemical reaction to form a coordinat ...

Applications

2-Methylimidazole is a precursor to the several members of the

nitroimidazole antibiotics Nitroimidazoles are the group of organic compounds consisting of an imidazole ring with at least one nitro group substituent. The term also refers to the class of antibiotics that have nitroimidazole in their structures. These antibiotics commonly ...

that are used to combat anaerobic bacterial and parasitic infections. File:Dimetridazole structure.svg,

Dimetridazole Dimetridazole is a drug that combats protozoan infections. It is a nitroimidazole class drug. It used to be commonly added to poultry feed. This led to it being found in eggs. Because of suspicions of it being carcinogenic its use has been legal ...

File:Metronidazole.svg,

Metronidazole Metronidazole, sold under the brand name Flagyl and Metrogyl among others, is an antibiotic and antiprotozoal medication. It is used either alone or with other antibiotics to treat pelvic inflammatory disease, endocarditis, and bacterial vagino ...

File:Secnidazole.svg,

Secnidazole Secnidazole (trade names Flagentyl, Sindose, Secnil, Solosec) is a nitroimidazole anti-infective used to treat bacterial vaginosis and trichomoniasis. It is taken orally. Structurally it actually methyl-metronidazole. Effectiveness in the tr ...

File:Ornidazole.svg,

Ornidazole Ornidazole is an antibiotic used to treat protozoan infections. A synthetic nitroimidazole, it is commercially obtained from an acid-catalyzed reaction between 2-methyl-5-nitroimidazole and epichlorohydrin. Ornidazole is nothing but chloro-secn ...

File:Tinidazole.svg,

Tinidazole Tinidazole, sold under the brand name Tindamax among others, is a medication used against protozoan infections. It is widely known throughout Europe and the developing world as a treatment for a variety of anaerobic amoebic and bacterial infecti ...

File:Carnidazole.svg ,

Carnidazole Carnidazole (trade names Spartrix, Pantrix, Gambamix) is an antiprotozoal drug of the nitroimidazole class used in veterinary medicine. It is used to treat ''Trichomonas ''Trichomonas'' is a genus of anaerobic excavate parasites of vertebra ...

Safety

It has low toxicity with an (rat, oral) of 1300 mg/kg, but it is strongly irritating to the skin and eyes. 2-Methylimidazole is a

REACH Regulation Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) is a European Union regulation dating from 18 December 2006, amended on 16 December 2008 by Regulation (EC) No 1272/2008. REACH addresses the production and use of che ...

Candidate

Substance of Very High Concern A substance of very high concern (SVHC) is a chemical substance (or part of a group of chemical substances) which has been proposed as a candidate for inclusion on the Authorization or Restriction list (seeECHA Lists of REACH. The addition of a ...

due to its endocrine disrupting properties.

References

{{DEFAULTSORT:Methylimidazole, 2- Imidazoles