1,2-Dimethyl-5-nitroimidazole
[CAS# 551-92-8]

Identification

• Classification: API >> Antiparasitic drug >> Antiprotozoal
• Name: 1,2-Dimethyl-5-nitroimidazole
• Synonyms: Dimetridazole; 1,2-Dimethyl-5-nitro-1H-imidazole
• Molecular Formula: C₅H₇N₃O₂
• Molecular Weight: 141.13
• CAS Registry Number: 551-92-8
• EC Number: 209-001-2
• SMILES: CC1=NC=C(N1C)[N+](=O)[O-]

Properties

• Melting point: 177-182 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H315-H319-H335-H341
• Safety Statements: P203-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1,2-Dimethyl-5-nitroimidazole is a chemical compound belonging to the class of nitroimidazoles, which are well known for their antibacterial, antiprotozoal, and antitumor properties. Nitroimidazole derivatives are widely used in the treatment of infections caused by anaerobic bacteria and certain protozoa.

The compound 1,2-dimethyl-5-nitroimidazole is characterized by the presence of a nitro group (-NO2) attached to the imidazole ring, which is a five-membered heterocyclic structure containing nitrogen atoms. The methyl groups at positions 1 and 2 on the imidazole ring contribute to its chemical properties, affecting its solubility and biological activity.

1,2-Dimethyl-5-nitroimidazole, like other nitroimidazoles, is primarily used for its antimicrobial activity. It exerts its effects by interfering with the DNA synthesis of microorganisms. The nitro group in the compound is reduced within the microbial cell to generate reactive intermediates, which then interact with the DNA, causing damage. This inhibits the ability of the organism to replicate and grow, leading to the death of the pathogen.

The compound is used in the treatment of infections caused by anaerobic bacteria, such as those that cause conditions like pelvic inflammatory disease, abscesses, and some gastrointestinal infections. Additionally, nitroimidazoles are effective against protozoal infections like amebiasis, giardiasis, and trichomoniasis. 1,2-Dimethyl-5-nitroimidazole, while not as commonly used as other nitroimidazole derivatives like metronidazole, shares similar pharmacological properties and may have specific applications in research or clinical settings where it is necessary to target anaerobic infections.

In terms of its pharmacological activity, 1,2-dimethyl-5-nitroimidazole has been studied for its potential use as an anticancer agent as well, though its primary applications remain in the antimicrobial and antiparasitic areas.

The compound is typically administered orally or intravenously, depending on the nature and severity of the infection. As with other nitroimidazoles, care must be taken to monitor for potential side effects such as gastrointestinal disturbances, neurotoxic effects, and, in rare cases, allergic reactions.

In conclusion, 1,2-dimethyl-5-nitroimidazole is a nitroimidazole derivative with antimicrobial, antiparasitic, and potentially anticancer properties. It is mainly used in the treatment of anaerobic bacterial and protozoal infections. The compound works by interfering with microbial DNA synthesis, leading to the inhibition of pathogen growth.

References

2024. Development of purity certified reference materials to establish metrological traceability for the measurement of nitroimidazoles in agricultural products. Analytical and Bioanalytical Chemistry, 416(28).
DOI: 10.1007/s00216-024-05530-3

2012. A comparative study on vibrational, conformational and electronic structure of 1,2-dimethyl-5-nitroimidazole and 2-methyl-5-nitroimidazole. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 97.
DOI: 10.1016/j.saa.2012.05.072