2-Methyl-5-Nitro Imidazole: From Origin to Opportunity

Historical Development

Back in the middle of the twentieth century, researchers looking for more powerful antimicrobial compounds turned their attention to imidazole derivatives. The addition of a methyl group at the second carbon and a nitro group at the fifth position led to a molecule both intriguing and practical. This marked a major step for chemistry and medicine, since scientists realized these structural tweaks directly influenced biological activity. Over decades, 2-Methyl-5-Nitro Imidazole earned attention as labs and pharmaceutical makers sought alternatives to more traditional treatments for protozoal and anaerobic bacterial infections. When resistance started creeping into households and hospitals, this compound’s roots became important for development strategies aiming to outpace bacterial adaptation.

Product Overview

2-Methyl-5-Nitro Imidazole shows up in labs as a pale yellow crystalline powder. Chemical suppliers often stock it for research, pharmaceutical processes, and intermediate use in synthesis. Its growth as a staple of microbiological testing and drug development can’t be separated from the demand for safer, effective agents to treat infections beyond the reach of simple penicillins or cephalosporins. Across the world, its availability has fueled new pharmaceutical syntheses and multiple generic product launches. Its unique placement among nitroimidazoles also supports unusual or hard-to-treat infection strategies, giving clinicians new tools against some stubborn pathogens.

Physical & Chemical Properties

This substance carries a molecular weight hovering around 155.13 g/mol and displays a melting point between 185 and 190°C. It resists easy dissolution in water yet blends smoothly with common organic solvents such as ethanol or dimethyl sulfoxide. It carries a slightly bitter odor, rarely strong enough to notice outside of pure form handling. The molecule holds tightly to its aromatic ring, with electron-rich nitrogen and oxygen atoms lending themselves to hydrogen bonding—something that shapes its behavior in both lab reactions and biological environments. Sensitivity to intense light and oxidative conditions means storage choices often focus on dry, cool, and dark environments.

Technical Specifications & Labeling

Laboratories must check for purity above 98 percent by HPLC or GC, with appearances rated regularly for color, consistency, and absence of foreign materials. Labels carry lot number, expiry date, country of origin, and manufacturer’s batch certifications for all clinical or research applications. Safety information, hazard pictograms, and recommended personal protective equipment show up at every purchasing level, from bulk shipment drums to research vials. Documentation standardizes around International Union of Pure and Applied Chemistry protocols and follows GO/No-GO criteria for active pharmaceutical ingredients, especially in regulated territories.

Preparation Method

Production generally begins with methylimidazole as a base compound, subjected to a controlled nitration process. This step uses a mixture of concentrated nitric acid and sulfuric acid under low temperatures to discourage runaway byproducts. The nitro group lands at the five-position through direct substitution, with yields locked in through careful adjustment of temperature, acid concentration, and agitation speed. Industrial routes repeat these steps with closed reactors and in-line cooling to minimize risk. Purification often includes repeated crystallization using ethanol or a similar medium, followed by vacuum drying to remove trace reagents.

Chemical Reactions & Modifications

The presence of both nitro and methyl groups means this molecule behaves distinctively compared to parent imidazole. The nitro moiety enables reduction to the corresponding amine, a key move in drug discovery and custom molecule design. Methyl, meanwhile, boosts lipophilicity and shifts selectivity in biological pathways. Derivatization at the N1 or additional substitutions across the ring allow medicinal chemists to deepen antimicrobial activity or slice away toxic effects. In organic chemistry, 2-Methyl-5-Nitro Imidazole acts as both a target for further synthetic building and a probe for studying electron transport inside cells. Reports have described alkylations and acylations, revealing wider applications in agrochemical and dye research, not just as an antibiotic precursor.

Synonyms & Product Names

Chemists call this compound by several other names: metronidazole intermediate, 2-Methyl-5-nitro-1H-imidazole, and 1H-Imidazole, 2-methyl-5-nitro. Trade and regulatory contexts may classify it under research numbers or internal company codes, depending on the place and intended application. Drug development teams and inventory controllers track these synonyms to align operational data, supply chain records, and regulatory registrations worldwide, since fragmented names could lead to delayed shipments or compliance gaps in multinational operations.

Safety & Operational Standards

Despite a strong safety profile in formulated drugs, handling concentrated 2-Methyl-5-Nitro Imidazole demands respect inside laboratories and pilot plants. Long-term exposure to powders or dust can irritate the skin and airways, calling for disposable gloves, safety glasses, and effective ventilation systems. Material Safety Data Sheets specify emergency actions for spills, accidental ingestion, and fire containment. Regulatory guidelines such as REACH and OSHA spell out exposure limits and prescribe labeling for transportation and storage. Anyone involved in regular handling receives targeted training, keeping workplace safety audits and environmental controls air-tight where these chemicals flow.

Application Area

This compound’s core action involves disrupting DNA synthesis in target organisms, a trait valuable for treating infections no longer responding to frontline antibiotics. It stands behind the clinical success of several antiprotozoal and antibacterial agents, including widely deployed nitroimidazole drugs like metronidazole and tinidazole. Beyond pharmaceuticals, researchers use it to illuminate pathways of microbial resistance and to create new test strains in microbiology. Industrial scale-ups have branched into production for veterinary drugs, environmental water testing agents, and plant protection blends where soil-borne pathogens threaten crop yields. Biotech pipelines see it as a springboard for building ever more selective anti-infective molecules.

Research & Development

Pharmaceutical innovators leverage 2-Methyl-5-Nitro Imidazole in screening programs designed to outmaneuver drug resistance, with teams focusing on new analogs that dodge emerging bacterial counter-mechanisms. Academic groups use it to model how nitro-containing drugs interact with human metabolic enzymes, hoping for breakthroughs in low-toxicity, high-potency drug forms. Synthesis and medicinal chemistry units automate reaction variations on its backbone to build focused libraries for testing in bacteria, protozoa, and even some fungal pathogens. Each new publication pushes understanding another step forward, leading to pipeline candidates in not just infection, but also inflammatory and oncological settings.

Toxicity Research

Scientists pay close attention to cellular and systemic safety, since nitroimidazoles have a checkered past regarding mutagenic and carcinogenic potential, especially under long-term or high-dose conditions. Rodent studies and cell assays map out metabolic breakdown products, revealing how even minor byproducts can trigger genotoxicity given sustained exposure. Toxicologists keep refining test models, factoring in not only direct human effects but also downstream impacts if the compound enters aquatic systems. Regulatory filings hinge on this research, as agencies demand proof that environmental, occupational, and clinical exposures stay well under harm thresholds defined by decades of animal and human data.

Future Prospects

Antibiotic resistance shows no sign of slowing down, so this molecule’s place remains as crucial as ever. The flexibility built into its structure encourages new thinking: combination therapies, site-targeted prodrugs, and next-layer modifications to sidestep resistance entirely. Environmental chemists have started adapting it to degrade faster after use, softening impact on wastewater systems and wildlife. Automated synthesis and artificial intelligence screening offer the promise of dozens of novel analogs rolled out in less time and at lower cost. Partnerships spring up between academic labs, private industry, and healthcare stakeholders, all betting that future generations of nitroimidazole-derived compounds will continue fending off the world’s stubbornest infections while minimizing risk for people and planet.




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2-Methyl-5-Nitro Imidazole
2-Methyl-5-Nitro Imidazole
2-Methyl-5-Nitro Imidazole