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Comprehensive Guide to 1-(8-Methylimidazo[1,2-a]pyridin-2-yl)methanamine Dihydrochloride (CAS 518064-47-6)

1-(8-Methylimidazo[1,2-a]pyridin-2-yl)methanamine dihydrochloride (CAS 518064-47-6) is a specialized organic compound gaining attention in pharmaceutical research and fine chemical synthesis. This dihydrochloride salt derivative of an imidazopyridine scaffold exhibits unique physicochemical properties that make it valuable for drug discovery applications. With the molecular formula C9H13Cl2N3, this compound belongs to the class of imidazo[1,2-a]pyridine derivatives, which have shown promising biological activities in recent studies.

The compound's structural features include a methyl-substituted imidazopyridine core with an aminomethyl functional group, rendered water-soluble through dihydrochloride salt formation. Researchers particularly value its balanced lipophilicity and water solubility (logP ~1.2), which contributes to good membrane permeability while maintaining sufficient aqueous solubility for biological testing. The crystalline powder form (typically white to off-white) has demonstrated excellent stability under standard storage conditions, with decomposition temperatures above 200°C.

In pharmaceutical applications, 1-(8-Methylimidazo[1,2-a]pyridin-2-yl)methanamine serves as a versatile building block for kinase inhibitor development. Recent publications highlight its use in creating selective inhibitors for protein kinases involved in inflammatory pathways, a hot topic in autoimmune disease research. The compound's amine functionality allows straightforward derivatization through amide coupling or reductive amination reactions, making it popular in combinatorial chemistry approaches.

The synthesis of CAS 518064-47-6 typically involves multi-step organic transformations starting from 2-amino-5-methylpyridine. Current optimization efforts focus on improving atom economy and reducing hazardous byproducts, aligning with green chemistry principles that dominate modern synthetic discussions. Analytical characterization by HPLC typically shows purity ≥98%, with NMR spectra confirming the expected proton environments (δ 2.5 ppm for methyl, 7.2-8.1 ppm for aromatic protons).

Market trends indicate growing demand for imidazo[1,2-a]pyridine-based intermediates, driven by increased research into their therapeutic potential. The global market for such heterocyclic compounds is projected to grow at 6.8% CAGR (2023-2030), with applications expanding beyond pharmaceuticals into materials science. Researchers frequently search for "buy 1-(8-Methylimidazo[1,2-a]pyridin-2-yl)methanamine dihydrochloride" or "CAS 518064-47-6 supplier," reflecting strong commercial interest.

From a safety perspective, standard laboratory precautions (gloves, goggles) are recommended when handling this compound. While not classified as highly hazardous, proper ventilation should be maintained during weighing operations. The material safety data sheet (MSDS) reports an LD50 >2000 mg/kg in rodent studies, indicating relatively low acute toxicity, though comprehensive ecotoxicological data remains limited.

Recent patent analyses reveal increasing incorporation of 1-(8-Methylimidazo[1,2-a]pyridin-2-yl)methanamine derivatives in drug candidates, particularly for neurological and metabolic disorders. Its structural motif appears in several clinical-stage molecules targeting G-protein-coupled receptors (GPCRs), a major focus area in current drug discovery. This aligns with frequent search queries about "imidazopyridine GPCR modulators" and "small molecule kinase inhibitors 2024."

For researchers considering this compound, important technical notes include: solubility in water (>50 mg/mL), recommended storage at 2-8°C under inert atmosphere, and compatibility with common organic solvents (DMSO, methanol, DMF). HPLC methods typically employ C18 columns with 0.1% TFA in water/acetonitrile gradients. The compound shows characteristic UV absorption at 265 nm, useful for analytical quantification.

The future outlook for CAS 518064-47-6 appears promising as structural biology advances enable better exploitation of its molecular interactions. Cryo-EM studies have recently visualized similar scaffolds bound to therapeutic targets, driving rational design approaches. With pharmaceutical companies increasingly screening imidazo[1,2-a]pyridine libraries, demand for this building block will likely accelerate in coming years.

Quality control specifications for commercial material typically include: appearance (white powder), melting point (228-232°C with decomposition), residual solvents (<0.5%), heavy metals (<10 ppm), and chromatographic purity (≥98% by HPLC). Reputable suppliers provide comprehensive analytical data packages including 1H/13C NMR, HRMS, and HPLC traces to verify identity and purity.

From a regulatory standpoint, 1-(8-Methylimidazo[1,2-a]pyridin-2-yl)methanamine dihydrochloride is not currently listed on any controlled substance schedules. However, researchers should consult local regulations regarding novel chemical entities, especially when considering export/import procedures. Proper documentation including certificates of analysis should accompany all shipments.

Emerging applications in materials science include use as a ligand in catalytic systems and as a building block for organic electronic materials. The compound's rigid aromatic system and coordination sites make it interesting for designing metal-organic frameworks (MOFs), a trending research area. This expands its relevance beyond traditional medicinal chemistry applications.

For those exploring structure-activity relationships, the 8-methyl group in this compound has shown significant effects on target binding affinity in published studies. Molecular modeling suggests this substituent influences the compound's binding orientation in enzyme active sites, making it valuable for lead optimization studies. Such insights address common researcher questions about "imidazopyridine structure-activity relationships."

In summary, 1-(8-Methylimidazo[1,2-a]pyridin-2-yl)methanamine dihydrochloride represents a valuable tool for modern drug discovery, with physicochemical properties and synthetic versatility that explain its growing popularity. As research into heterocyclic compounds advances, this CAS 518064-47-6 material will likely find expanded applications across multiple scientific disciplines.

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