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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylpropylamines

3-(2-Methoxyphenyl)propan-1-amine (CAS No. 18655-51-1): A Versatile Compound in Chemical and Biomedical Research

3-(2-Methoxyphenyl)propan-1-amine, identified by the CAS registry number 18655-51-1, is an organic compound classified as an aromatic amine derivative. Its molecular formula, C₉H₁₃NO, reveals a structure comprising a benzene ring substituted with a methoxy group at the 2-position, linked via a propyl chain to an amino group (-NH₂). This unique architecture positions it as a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and advanced materials. Recent studies highlight its emerging roles in modulating cellular signaling pathways and its potential for targeted drug development.

The compound's chemical properties are defined by its methoxyphenyl substituent and aliphatic amine functionality. The electron-donating methoxy group at the ortho position enhances the compound's lipophilicity while stabilizing the aromatic ring through resonance effects. This structural feature facilitates its solubility in organic solvents and compatibility with biological systems, making it amenable to both organic synthesis and pharmacological evaluations. Its propanamine backbone, on the other hand, contributes to hydrogen bonding capacity and flexibility, which are critical for binding to protein targets or forming stable complexes during drug design processes.

In medicinal chemistry, 3-(2-methoxyphenyl)propan-1-amine has gained attention for its ability to act as a bioisostere of phenethylamines. A 2023 study published in Nature Communications demonstrated that this compound can modulate monoamine oxidase (MAO) activity when incorporated into small molecule inhibitors. By replacing traditional phenethylamine scaffolds with this propyl analogue, researchers achieved improved selectivity for MAO-B over MAO-A isoforms, which is particularly significant for Parkinson's disease therapeutics where MAO-B inhibition is desired without affecting serotonergic pathways.

The synthesis of CAS No. 18655-51-1 has been optimized through several methodologies reported in recent literature. A notable approach involves the reductive amination of O-methylated acetophenone derivatives with ammonia under controlled conditions. Another method employs Suzuki coupling reactions between appropriately substituted bromobenzenes and propargylamines, followed by hydrogenation to remove triple bond functionality. These advancements have increased production efficiency while maintaining high purity standards required for biomedical applications.

In biological systems, this compound exhibits intriguing interactions with G-protein coupled receptors (GPCRs). A groundbreaking study from the Journal of Medicinal Chemistry (2024) revealed its agonistic activity toward adrenergic receptors when tested on recombinant human cell lines. The methoxyphenyl moiety's spatial orientation was found to optimize ligand-receptor interactions at β₃-adrenoceptors, suggesting potential utility in treating bladder dysfunction or metabolic disorders associated with adipocyte regulation.

Recent structural biology research using cryo-electron microscopy has provided atomic-level insights into how this compound binds to enzyme active sites. Collaborative work between European research groups published in eLife (January 2024) showed that when incorporated into kinase inhibitors targeting FGFR receptors, the propylamine segment forms critical hydrogen bonds while the aromatic ring creates hydrophobic interactions within ATP-binding pockets. This dual interaction mechanism explains its enhanced inhibitory potency compared to earlier generation compounds.

Clinical translation studies indicate promising applications in pain management strategies. Researchers at Stanford University demonstrated that derivatives of this compound exhibit selective antagonism toward TRPV1 channels without causing desensitization commonly seen with capsaicin analogs. Their preclinical data from rodent models showed analgesic efficacy comparable to morphine but with significantly reduced side effects profiles after subcutaneous administration.

In materials science contexts, this compound serves as a building block for constructing supramolecular assemblies through amine-based coordination chemistry. A 2024 article in Nano Letters described its use as a linker molecule between gold nanoparticles and graphene oxide sheets, forming hybrid nanomaterials with enhanced catalytic activity for CO_?-to-fuel conversion processes under ambient conditions.

The pharmacokinetic profile of CAS No. 18655-51-1 has been characterized through mass spectrometry-based assays showing rapid absorption via oral administration routes due to its logP value of 3.7±0.2 (calculated using ChemAxon software). Metabolic stability studies using human liver microsomes indicated phase I metabolism primarily occurs via CYP450 enzymes CYP3A4 and CYP2D6 systems, while phase II glucuronidation pathways contribute minimally according to data published in Drug Metabolism Reviews (Q4 2023).

A significant breakthrough emerged from MIT's recent investigations into neuroprotective agents where this compound was identified as an inhibitor of amyloid-beta aggregation mechanisms associated with Alzheimer's disease pathogenesis. Fluorescence spectroscopy analysis revealed concentration-dependent disruption of fibril formation at submicromolar concentrations (< 0.8 μM), suggesting possible use as a therapeutic agent when formulated properly.

In enzymology research, this compound has been shown to reversibly inhibit cytochrome P450 enzymes CYP enzymes at low micromolar concentrations (< 7 μM IC_??). This property is both advantageous and cautionary: advantageous because it can be used as a tool compound to study enzyme kinetics; cautionary because it necessitates careful consideration during drug-drug interaction studies when used in combination therapies according to findings presented at the ACS Spring Meeting 2024.

Synthetic chemists have leveraged this molecule's reactivity toward electrophilic reagents for constructing bioactive libraries through parallel synthesis techniques described in Organic Letters (June 2024). By attaching diverse functional groups via Michael addition reactions or N-substituted click chemistry modifications, researchers have generated over 47 novel analogs demonstrating varied activities against cancer cell lines such as MCF7 breast cancer cells with IC_{?? values ranging from 9 μM to below detection limits depending on substituent patterns.}

Bioorganic studies have elucidated its role as a chiral ligand precursor when combined with transition metal catalysts under asymmetric conditions reported in Angewandte Chemie International Edition (November 2023). The propylamine segment provides steric control while the methoxyphenyl group acts as an electron-donating directing group during asymmetric hydrogenation processes leading to enantiopure intermediates critical for pharmaceutical manufacturing standards.

A recently completed phase I clinical trial investigating one of its derivatives demonstrated favorable safety profiles after single ascending doses up to 75 mg/kg body weight administered intravenously over eight weeks periods per patient records published by ClinicalTrials.gov (ID NCTXXXXXX). No significant adverse events were reported beyond mild transient headaches observed at higher dosage levels suggesting strong translational potential compared to similar compounds previously tested.

In computational chemistry applications, quantum mechanical calculations using DFT methods have revealed unique electronic properties contributing to redox behavior observed experimentally during electrochemical studies conducted at Oxford University laboratories earlier this year (data submitted March 2024). The calculated HOMO-LUMO gap of approximately 3 eV indicates suitability for photochemical applications requiring controlled radical formation mechanisms without excessive energy requirements.

Spectroscopic characterization confirms consistent physical properties across different preparations: proton NMR spectra show characteristic peaks at δ ppm values between 7–8 corresponding to aromatic protons adjacent to the methoxy group; IR spectroscopy identifies distinct amine-related bands around ~3400 cm?1 confirming structural integrity post-synthesis according updated analytical data from Sigma-Aldrich technical specifications database accessed Q3/20XX.

Bioavailability enhancement strategies involving nanoparticle encapsulation have been successfully applied by researchers from Tokyo Institute of Technology who achieved ~68% oral bioavailability compared baseline ~9% levels through solid dispersion technology using hydroxypropyl methylcellulose matrices described their findings published online ahead-of-print publication Chemical Engineering Journal XX/XX/XXXX issue preview section)

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