The story of 3-Aminopyrazine-2-carboxylic acid stretches back to the mid-20th century, built around a growing understanding of pyrazine derivatives. Researchers in organic chemistry took interest due to the versatility of pyrazine rings and their clear impact on medicinal chemistry. Early syntheses borrowed from classical methods, often producing small yields, which frustrated those working in both academic and industrial laboratories. Over time, optimization followed, driven by the promise of new antibacterial, antifungal, and agricultural products. Generations of chemists passed down modifications, accumulating a body of knowledge that now supports its routine preparation. Looking back, the journey saw basic research in heterocyclic chemistry shift toward targeted synthesis, analytical advances, and growing industrial uptake.
The compound 3-Aminopyrazine-2-carboxylic acid has earned a place on the shelf of any serious lab working with fine chemicals, agrochemical intermediates, or potential pharmaceuticals. Its unique pyrazine backbone, with strategically placed amino and carboxylic acid groups, makes it attractive for both direct application and further modification. Scientists value its reliability as a building block and intermediate, particularly when constructing molecules where electron distribution and hydrogen bonding are key. The molecule doesn’t just serve a single market; it brings practical value to drug discovery, diagnostics, and even niche materials research.
This solid appears off-white or pale yellow and sports a molecular formula of C5H5N3O2, with a molar mass around 139.12 g/mol. Its melting point sits between 260°C and 270°C, which is high enough to keep worries about accidental melting to a minimum during handling or reactions. The chemical structure features a six-membered aromatic ring, boasting one amino group at position three and a carboxylic acid at position two. Solubility in water stays moderate, though it swells in DMF or DMSO, and those working with the solid must watch for its tendency to form strong intra- and intermolecular hydrogen bonds. Acidity corresponds to the carboxylic group, while the ring also supports nucleophilic substitutions due to the electron-withdrawing nature of the adjacent nitrogen atoms.
Quality-conscious users often call for purity above 97%, with HPLC and NMR serving as mainstays in confirming batch consistency. Labels on commercial products cite the CAS Number 7415-67-6, storage instructions (cool, dry places), and warning information tied to its irritant risk profile. Package sizes stretch from grams for academic work up to kilograms for process research teams. Certificates of analysis detail trace impurities, water content by Karl Fischer testing, and the permissible heavy metal concentration—key variables for regulatory compliance. Reference to batch numbers and synthesis conditions make traceability on par with best practices for research and safe industrial deployment.
Synthesizing 3-aminopyrazine-2-carboxylic acid usually begins with a substituted pyrazine precursor, often pyrazine-2-carboxylic acid or an analogous ester. Amination of the pyrazine ring can take several approaches, but direct introduction of the amino group at the three position remains dominant, using reagents like ammonia or amines in polar solvents under elevated temperatures. Reduction of nitro groups or other protected intermediates extends the synthetic options. Process chemists find that optimizing pH, solvent, and reaction times brings higher yields and cleaner products, reducing the need for laborious purification steps. Industrial players push toward greener, catalytic routes, not just for efficiency but to cut down on waste and energy consumption.
The molecule stands out for its chemical flexibility. Carboxyl groups open opportunities for amide coupling and esterification, fundamental in producing peptide mimetics and drug candidates. Amino groups enter acylation, sulfonation, and diazotization, connecting to dyes, agrochemicals, and advanced materials. Selective substitutions on the pyrazine ring allow design of novel analogs, with medicinal chemists using every handle the molecule offers. One vivid example lies in linking the carboxylic acid to form prodrugs, altering pharmacokinetic profiles to boost bioavailability. Academics likewise use the compound’s core for preparing coordination complexes, exploring catalysis or materials science possibilities.
In shipping orders and scientific papers alike, 3-aminopyrazine-2-carboxylic acid may appear as “3-APCA,” “2-pyrazinecarboxylic acid, 3-amino-,” or by catalog numbers from major suppliers. Some texts reference it as “3-aminopyrazine-2-carboxylate acid” or “pyrazinecarboxylic acid, 3-amino,” reflecting slight shifts in naming conventions over time or by region. These synonyms shape literature searches, enforce consistency across supply chains, and guide regulatory submissions, helping evade confusion amid similar-sounding analogs.
Every lab user quickly learns to respect this material, not for high acute toxicity but because safety protocols help avoid skin, eye, and respiratory irritation. Lab coats, gloves, and properly vented hoods strike a balance between productivity and well-being. Spills or contact with incompatible reagents risk forming mild irritants—quick cleanup and timely disposal become habits. Packaging follows hazardous material guidelines, with labeling echoing globally harmonized system standards. Training on storage stability and container integrity guards against moisture ingress, which might degrade the material or complicate downstream use. Industrial settings introduce more formal precautions, involving exposure monitoring, material safety data sheets, and routine risk assessments before scaling up processes. Shipping remains subject to standard transport regulations, particularly for bulk quantities destined for pharmaceutical or specialty chemical applications.
Opinions on its main value depend on the professional background. Pharmaceutical researchers see it primarily as a precursor for drugs targeting tuberculosis, other bacterial infections, or rare metabolic conditions. Agrochemical companies use it for herbicide and fungicide development, leaning on its compatibility as a core structure for synthetic analogs. Diagnostics and analytical chemistry benefit from derivatives with strong affinity for metal ions, supporting imaging or quantification. Recent years saw a surge in investigating its behavior in polymer chemistry, giving rise to new smart materials that respond to pH or other triggers. The reach of its applications reflects a broad commitment to extracting practical outcomes from chemical innovation, building value not just for industry but for public health and research communities.
Ongoing research finds companies and universities fine-tuning both synthesis and application. Many current efforts look to shorten synthetic routes or use renewable feedstocks. At the same time, teams continue expanding structure-activity relationships, combing through analog libraries for compounds with greater antimicrobial or antifungal properties. Analytical chemists leverage NMR, MS, and crystallography to better understand tautomerism, hydrogen bonding, and solid-state forms, each affecting how the compound performs in real-world settings. Collaboration between industry and academia helps move promising analogs from the bench to preclinical trials, pooling resources in a mutually beneficial cycle of discovery. Companies also invest in education and training, building up the next wave of scientists fluent in both theory and practice surrounding this and related molecules.
Studies on this compound show relatively low acute toxicity, yet chronic exposure concerns persist, especially for workers handling large volumes or in settings where controls may slip. Toxicologists track metabolic breakdown in animal models, noting any formation of genotoxic metabolites. Environmental safety teams evaluate persistence in soil and water, seeking to minimize the load of synthetic intermediates in ecosystems. Many journals require rigorous safety data before publishing new applications, reflecting growing social and regulatory pressure to close knowledge gaps on risk factors. For users, this means monitoring for updates in allowable exposure levels, keeping informed of new data as regulatory landscapes change.
Expanding markets for personalized medicine likely boost demand for building blocks like 3-aminopyrazine-2-carboxylic acid, encouraging new investment in next-generation synthesis and analytics. The search for antimicrobial solutions in the face of drug resistance continues to drive structural modification, with fragment-based drug design making creative use of this scaffold. Green chemistry is shifting the production model, with catalysis, solvent recycling, and renewable inputs quickly moving into the mainstream. Meanwhile, educational and open data initiatives give a wider audience a chance to access best practices and contribute fresh ideas. The journey of this molecule, from bench curiosity to core industrial intermediate, says a lot about what's possible when basic science, practical need, and shared knowledge push each other forward.
