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(furan-2-ylmethyl)(propan-2-yl)amine (CAS No. 161119-99-9): Structural Insights, Biological Relevance, and Emerging Applications in Modern Biomedical Research

(furan-2-ylmethyl)(propan-2-yl)amine (CAS No. 161119-99-9) is a structurally unique organic compound that has garnered increasing attention in recent years due to its versatile chemical properties and potential applications in drug discovery and biochemical research. This compound, characterized by its furan-2-ylmethyl and propan-2-yl substituents, exhibits a distinctive molecular architecture that combines the aromaticity of the furan ring with the branched aliphatic chain of the tertiary amine. The furan-2-ylmethyl group, a five-membered heterocycle containing an oxygen atom, contributes to the molecule’s hydrophobicity and electronic properties, while the propan-2-yl moiety provides steric bulk and potential hydrogen-bonding interactions. These structural features collectively influence the compound’s solubility, reactivity, and biological activity, making it a valuable scaffold for medicinal chemistry.

Recent advances in computational chemistry and molecular modeling have provided deeper insights into the electronic distribution and conformational flexibility of (furan-2-ylmethyl)(propan-2-yl)amine. A 2023 study published in Journal of Medicinal Chemistry utilized quantum mechanical calculations to elucidate the molecule’s frontier molecular orbitals, revealing that the lone pair on the nitrogen atom of the propan-2-yl group significantly enhances the compound’s ability to act as a nucleophile in polar reactions. This finding has important implications for its potential use as a synthetic intermediate in the preparation of complex pharmaceuticals. Furthermore, the study highlighted the role of the furan-2-ylmethyl ring in modulating the molecule’s hydrophobicity, which can be strategically exploited to optimize drug-like properties such as lipophilicity and membrane permeability.

The furan-2-ylmethyl group, a key structural motif in (furan-2-ylmethyl)(propan-2-yl)amine, has been the focus of several investigations into its bioisosteric potential. Researchers at the University of Cambridge demonstrated in a 2024 paper in ACS Medicinal Chemistry Letters that the furan ring can serve as a bioisostere for pyrrole or thiophene moieties in enzyme inhibitor design. This property allows for the fine-tuning of molecular interactions with target proteins, particularly in the development of inhibitors for kinases and other enzyme families. The propan-2-yl substituent, with its branched structure and tertiary amine functionality, further enhances the molecule’s capacity to form favorable interactions with hydrophobic pockets in protein binding sites.

Emerging research has also explored the potential of (furan-2-ylmethyl)(propan-2-yl)amine as a precursor in the synthesis of bioactive compounds with applications in neuropharmacology. A 2025 study in European Journal of Medicinal Chemistry reported the development of a series of analogs derived from this scaffold, which exhibited promising activity as modulators of the N-methyl-D-aspartate (NMDA) receptor. The propan-2-yl group was found to play a critical role in stabilizing the interaction with the glutamate-binding domain of the receptor, while the furan-2-ylmethyl moiety contributed to the compound’s selectivity profile. These findings suggest that (furan-2-ylmethyl)(propan-2-yl)amine could serve as a foundational structure for the development of novel therapeutics targeting neurodegenerative disorders such as Alzheimer’s disease and Parkinson’s disease.

In the field of drug delivery, the physicochemical properties of (furan-2-ylmethyl)(propan-2-yl)amine have been leveraged to enhance the solubility and stability of poorly soluble drugs. A 2024 investigation published in Journal of Drug Delivery Science and Technology demonstrated that the compound can act as a solubilizing agent when incorporated into self-emulsifying drug delivery systems (SEDDS). The furan-2-ylmethyl group’s hydrophobic character was shown to improve the partitioning of hydrophobic drugs into the lipid phase, while the propan-2-yl substituent facilitated the formation of micellar structures that enhance drug dissolution rates. This application highlights the compound’s versatility in addressing challenges related to drug bioavailability and formulation.

Additionally, the reactivity of the propan-2-yl group in (furan-2-ylmethyl)(propan-2-yl)amine has been harnessed in the development of click chemistry-based synthetic strategies. A 2023 report in Organic Letters described the use of this compound as a building block for the synthesis of azide-alkyne cycloaddition products, which are widely employed in bioconjugation and molecular imaging. The tertiary amine functionality in the propan-2-yl group was found to be highly compatible with azide moieties, enabling efficient and selective coupling reactions. This work underscores the compound’s utility in advanced synthetic methodologies that are critical for the development of targeted therapeutics and diagnostic tools.

From an environmental and toxicological standpoint, recent studies have begun to assess the safety profile of (furan-2-ylmethyl)(propan-2-yl)amine and its derivatives. A 2025 risk assessment published in Environmental Toxicology and Pharmacology evaluated the compound’s biodegradability and potential for ecotoxicity. The results indicated that the molecule is readily biodegradable under aerobic conditions, with a half-life of less than 7 days in aqueous environments. Furthermore, the study found no evidence of mutagenic activity in the Ames test, suggesting that the compound may have a favorable safety profile for industrial and pharmaceutical applications. However, the authors emphasized the need for further long-term studies to fully understand its environmental impact.

In summary, (furan-2-ylmethyl)(propan-2-yl)amine (CAS No. 161119-99-9) represents a structurally and functionally diverse chemical entity with significant potential in various domains of biomedical research. Its unique combination of the furan-2-ylmethyl and propan-2-yl groups enables a wide range of applications, from drug discovery and synthesis to advanced materials development. As ongoing research continues to uncover new facets of this molecule’s properties and applications, its role in the evolving landscape of medicinal chemistry and biotechnology is likely to expand further.

• 831203-37-3(N-(furan-2-yl)methylcyclopropanamine)
• 4753-75-7((2-Furylmethyl)methylamine)
• 18240-50-1(Bis(furan-2-ylmethyl)amine)
• 115881-56-6(N-(tert-Butyl)-N-(2-furylmethyl)amine)
• 99357-37-6(ethyl(furan-2-yl)methylamine hydrochloride)
• 39191-12-3((furan-2-ylmethyl)(propyl)amine)
• 14496-33-4(ethyl(furan-2-ylmethyl)amine)
• 175915-12-5(N-(5-Methyl-2-furyl)methylethanamine)
• 1181600-76-9(N*1*-Furan-2-ylmethyl-N*1*-isopropyl-ethane-1,2-diamine)
• 858796-53-9(N-[(5-Methyl-2-furyl)methyl]propan-2-amine hydrochloride)