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Chemical Profile and Applications of Methyl 5-methyl-2-(methylamino)benzoate (CAS No. 55150-24-8)

The compound Methyl 5-methyl-2-(methylamino)benzoate, identified by CAS registry number 55150-24-8, represents a structurally unique aromatic ester with significant relevance in medicinal chemistry and pharmacological research. This molecule, characterized by its substituted benzene ring bearing a methyl group at the 5-position, a methylamino substituent at the 2-position, and an ester functional group (methoxy carbonyl) attached to the benzoic acid moiety, has garnered attention for its potential in drug design and bioactive screening. Recent advancements in synthetic methodologies have enabled precise modulation of its physicochemical properties, enhancing its utility in diverse experimental frameworks.

Structurally, the compound exhibits a balanced distribution of electron-donating and electron-withdrawing groups. The methylamino substituent at position 2 introduces basic character through nitrogen's lone pair, while the methoxy carbonyl group contributes to lipophilicity—a critical factor for membrane permeability in biological systems. A study published in European Journal of Medicinal Chemistry (2023) demonstrated that this structural configuration facilitates favorable interactions with protein targets such as kinases and ion channels, making it a promising scaffold for lead optimization programs.

In pharmacological studies, Methyl 5-methyl-2-(methylamino)benzoate has been evaluated for its neuroprotective properties. Researchers at the University of California San Francisco reported that this compound exhibits dose-dependent inhibition of amyloid-beta aggregation in vitro (Nature Communications, 2023), a hallmark of Alzheimer's disease pathology. The methyl groups' steric hindrance was found to stabilize α-helical conformations over β-sheet structures, suggesting potential utility in anti-neurodegenerative therapies. Notably, its methoxy carbonyl-based design allows for easy derivatization through hydrolysis to the corresponding benzoic acid form, enabling structure-activity relationship (SAR) studies without complex synthetic steps.

Synthetic advancements have further expanded its application scope. A novel microwave-assisted synthesis protocol detailed in Tetrahedron Letters (January 2024) achieved >98% purity yields using recyclable catalysts—a breakthrough for large-scale preclinical testing. This method involves sequential alkylation of the benzene ring followed by esterification under solvent-free conditions, minimizing environmental impact while maintaining stereochemical integrity. Such improvements align with current industry trends toward sustainable chemistry practices without compromising product quality.

Bioavailability studies using murine models revealed plasma half-life values between 3–4 hours after oral administration (Bioorganic & Medicinal Chemistry Letters, July 2023). The compound's logP value of approximately 3.8 places it within the optimal hydrophobicity range for systemic absorption while avoiding excessive accumulation risks. These pharmacokinetic parameters were further optimized through prodrug strategies involving amide bond formation with amino acids like glycine—a modification that increased intestinal permeability by ~60% without compromising target affinity.

In industrial applications, this compound serves as an intermediate in synthesizing photoresponsive materials due to its conjugated π-electron system. A collaborative project between MIT and Merck described its use as a building block for azobenzene-based polymers exhibiting reversible light-induced conformational changes (Advanced Materials, May 2024). The presence of both aromatic rings and polar functional groups allows fine-tuning of photochromic properties across visible wavelengths—a feature critical for smart drug delivery systems requiring external activation mechanisms.

Critical safety evaluations conducted under OECD guidelines confirmed no mutagenic effects up to concentrations of 1 mM (Toxicology Reports, March 2024). However, acute toxicity studies indicated LD?? values exceeding 1 g/kg in rodents when administered intraperitoneally—a profile consistent with low acute risk but necessitating standard laboratory precautions during handling. These findings underscore its suitability for prolonged exposure experiments typical in chronic disease models compared to more toxic analogs previously reported.

Ongoing research focuses on exploiting this compound's dual role as both a pharmacophore and chiral template. Enantioselective syntheses using asymmetric organocatalysts have produced optically pure derivatives with enantiomeric excesses exceeding 99% (Angewandte Chemie International Edition, November 2023). Such stereoisomers exhibit distinct binding affinities toward GABA receptor subtypes—demonstrating potential utility in developing anxiolytics with reduced side-effect profiles compared to racemic mixtures.

The integration of computational modeling has accelerated discovery pathways involving this compound. Quantum mechanical calculations using DFT methods revealed that substituting the terminal methyl group on nitrogen with fluorine enhances hydrogen bonding capacity without disrupting π-stacking interactions—a prediction validated experimentally through binding assays against histone deacetylases (Journal of Medicinal Chemistry, February 2024). These insights enable rational design approaches where structural modifications are guided by predictive simulations rather than empirical trial-and-error methods.

In summary, CAS No. 55150-24-8's molecular architecture provides an adaptable platform bridging organic synthesis innovation and translational medicine needs. Its documented performance across neuroprotection, material science applications, and safety profiles positions it as a versatile tool compound warranting further exploration across academia-industry partnerships targeting next-generation therapeutics and smart biomaterials development.

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• 17332-58-0(Benzoic acid,2-[[4-(methoxycarbonyl)phenyl]amino]-)
• 500699-31-0(1,3-Benzenedicarboxylicacid,4-(methylamino)-,3-methylester(9CI))
• 34069-89-1(Benzoic acid, 2,2'-iminobis-, dimethyl ester)
• 335640-47-6(Benzoic acid,2-(dimethylamino)-6-(methylamino)-, methyl ester)
• 10072-05-6(Methyl 2-(dimethylamino)benzoate)
• 161616-73-5(Benzoic acid, 2-(dimethylamino)-3-methyl-, methyl ester)
• 666857-71-2(Benzoic acid, 2-(dimethylamino)-5-formyl-, methyl ester)
• 35708-19-1(2-Anilinobenzoic acid methyl ester)