1-(Allyl)Pyrrolidine-2-Methylamine: From Discovery to Application

Historical Development

Chemists have a longstanding curiosity for heterocyclic amines, and ever since organic synthesis matured in the late nineteenth century, pyrrolidine rings have enticed researchers. The roots of 1-(Allyl)Pyrrolidine-2-Methylamine go back to classic alkylamine research. Large pharmaceutical labs developed analogs to test new leads in neurological therapies, especially during the medicinal chemistry renaissance of the late 1900s. Treatment options for central nervous system disorders often sprung from small tweaks to simple cyclic amines, and this molecule found its place in diverse screening libraries as methods for selective amination and functional group interconversions improved. Over the past couple of decades, investment in tailored cyclic amines only increased, so 1-(Allyl)Pyrrolidine-2-Methylamine naturally became more visible in both reference collections and process chemistry blueprints.

Product Overview

1-(Allyl)Pyrrolidine-2-Methylamine brings together a five-membered nitrogen ring and an allyl group with a methylamine function on the ring. Raw material supply for each precursor—allyl halides, pyrrolidine intermediates, methylamine reagents—flows from large-scale chemical production. Labs target this molecule for both its energized reactivity and manageable stability, striking a balance that allows easy use but stores well under proper conditions. Small-molecule researchers and process chemists draw on the options provided by this structure for both chemical and biological explorations. Its backbone remains approachable for further alteration, without presenting excessive synthetic headaches.

Physical & Chemical Properties

1-(Allyl)Pyrrolidine-2-Methylamine presents as a colorless to pale yellow liquid under ambient conditions. It offers low to moderate solubility in water, but dissolves well in standard organic solvents such as ether, dichloromethane, and ethanol. Boiling and melting points line up with related pyrrolidine frameworks, landing well above room temperature for melting, and just high enough that distillation applies for purification. The molecule tends to release a faint, amine-like odor, and batch quality connects to trace moisture levels. Acid/base behavior follows established trends for secondary amines, making it friendly for both acid extraction and salt formation when needed in process streams or intermediate isolation.

Technical Specifications & Labeling

Bulk shipments arrive with certificates of analysis specifying assay (typically 97% or higher), main impurity profile, water content, and residue on ignition. Containers include GHS labels describing flammability, health hazards, and handling advice. MSDS documentation provides flashpoint and storage requirements. Some manufacturers offer NMR and GC/MS charts for batch verification; regulatory detail reflects national and regional transport and commerce laws. For projects in pharmaceutical or biotech spaces, regulatory-grade lots require audit trails for raw materials and cleaning logs for vessels.

Preparation Method

Most routes start from pyrrolidine or substituted pyrrolidines. Alkylation proceeds with allyl bromide or chloride, often using base (like K2CO3) in polar, aprotic solvents. The methylamine group attaches either before or after allylation, by direct amination under pressure with methylamine gas, or via amide reduction when less reactive intermediates make more sense. After reaction completion, organic extraction removes impurities, and distillation or chromatography yields a clean product. Researchers accustomed to fine-tuning reaction schedules adjust pressure, temperature, and substrate ratios to favor desired ring and side chain selectivity, using TLC or LC/MS to monitor progress.

Chemical Reactions & Modifications

The nitrogen atoms in 1-(Allyl)Pyrrolidine-2-Methylamine allow significant flexibility for chemical manipulation. Acylation, sulfonation, or protection of the amine can generate derivatives ready for coupling or polymerization. The allyl group withstands moderate acids and bases but transforms under conditions promoting electrophilic addition, such as catalytic hydrogenation or epoxidation. Scientists seeking novel pharmaceutical scaffolds add functional groups via selective oxidation of the allyl chain or use cross-coupling with transition metal catalysts. The ring structure resists hydrolysis, but N-alkylation with longer chains or aryl halides introduces further diversity, facilitating structure-activity relationship (SAR) experiments in drug discovery.

Synonyms & Product Names

Complex molecules accrue a handful of synonyms to aid their tracking and referencing. In catalogs, 1-(Allyl)Pyrrolidine-2-Methylamine appears as N-Allyl-2-methylaminopyrrolidine or 2-(Methylamino)-1-allylpyrrolidine. Internal project codes in pharmaceutical pipelines may obscure its structure. The chemical’s registry numbers (CAS, EC) help cross-search suppliers and regulatory reports. Some reference works and safety charts surface alternative spellings based on IUPAC translations or regional language conventions.

Safety & Operational Standards

Chemists handling small alkylamines encounter skin and respiratory irritation quickly if protection lapses. 1-(Allyl)Pyrrolidine-2-Methylamine reacts sharply with oxidizers or acids, so separating it from peroxides or acidic waste cuts down on unwanted byproducts. Fume hoods become non-negotiable even in low-volume settings. Some batches emit eyes-tingling fumes, so gloves and goggles accompany every handling session. In scale-up, vapor suppression and air monitoring keep workplace exposure below threshold limits found in occupational guidelines. Storage uses sealed amber glass or lined steel drums, away from direct sunlight and moisture. Facilities pursue documented accident response plans incorporating eye wash stations, spill control, and neutralizing agents tailored to both flammable liquid and corrosive hazard classes.

Application Area

Medicinal chemistry teams prize 1-(Allyl)Pyrrolidine-2-Methylamine for neuroactive compound research and as a base for synthetic tuning in structure-based drug design. Biotech labs look for its scaffold in screening programs exploring ion channel modulation or enzyme inhibition. Its derivative pathways plug directly into routes building up antivirals, CNS drugs, or agricultural actives. In material science, this amine’s backbone fits well for testing charge transport or polymer stabilization in specialty coatings. Analytical chemists reference it as a model system for method validation, tracking reactivity under stress, or benchmarking NMR/IR parameters. Some university teams pick up the molecule as a core for site-specific labeling, bioisosteric swaps, or late-stage functionalization exercises in training advanced students.

Research & Development

Activity in academic and industrial pipelines around pyrrolidine-based amines remains brisk. Teams optimize protocols for cost and yield, experimenting with green chemistry choices such as water-based media or reusable catalysts. Results from SAR campaigns push modifications with more polar or branched amine subunits, hoping to boost biological target affinity without sacrificing solubility. Researchers regularly report on new routes employing flow chemistry and continuous manufacturing for higher repeatability. The molecule also gets plugged into computational chemistry exercises, supporting virtual screening or property prediction for lead generation in multi-target projects.

Toxicity Research

Animal testing and in vitro models underpin most toxicity assessments. Early screens look at acute exposure, documenting effects on respiration, nervous system, and skin. Studies of 1-(Allyl)Pyrrolidine-2-Methylamine found moderate toxicity at high doses, mainly tied to its amine groups interacting with neurotransmission pathways. Chronic exposure research follows, watching for liver or renal stress after repeated dosing. Labs note genotoxicity and mutagenicity through Ames tests and chromosome aberration studies, generally flagging doses above those used in screening applications. Human data stays limited, but reports from synthetic labs emphasize the importance of avoiding skin contamination and inhalation. Regulatory agencies review these findings before issuing workplace limits or environmental discharge stipulations.

Future Prospects

1-(Allyl)Pyrrolidine-2-Methylamine looks set for greater importance in both drug discovery and process engineering. With automation and AI-driven synthesis readouts transforming lab workflows, molecules with adaptable reactivity like this one find more opportunities in combinatorial settings. Green chemistry initiatives find this scaffold attractive because the core reactions require fewer toxic catalysts and lend themselves to water-based or recyclable solvent systems. The push for CNS therapeutics and advanced agricultural actives ensures continued screening and modification. As materials science demands new building blocks for electronics and smart coatings, the pyrrolidine-allyl-methylamine structure promises pathways to functionalized monomers. Regulatory trends demanding lower emissions and safer workplaces mean safer-by-design practices will feed back into every stage of this compound’s use, shaping packaging, labeling, and risk management for years ahead.




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1-(Allyl)Pyrrolidine-2-Methylamine
1-(Allyl)Pyrrolidine-2-Methylamine
1-(Allyl)Pyrrolidine-2-Methylamine