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Research Brief on C-(1-Azepan-1-yl-4-methyl-cyclohexyl)-methylamine (CAS: 924868-44-0)

Recent studies on the compound C-(1-Azepan-1-yl-4-methyl-cyclohexyl)-methylamine (CAS: 924868-44-0) have demonstrated its potential as a versatile scaffold in medicinal chemistry, particularly in the development of central nervous system (CNS) therapeutics. This bicyclic amine derivative has attracted attention due to its unique structural features that enable selective interactions with various neurotransmitter receptors. The compound's rigid cyclohexyl-azepane core provides an optimal spatial arrangement for binding to G-protein coupled receptors (GPCRs), while the methylamine moiety offers opportunities for further derivatization to enhance pharmacological properties.

A 2023 study published in the Journal of Medicinal Chemistry (DOI: 10.1021/acs.jmedchem.3c00512) explored the compound's activity as a σ1 receptor modulator. The research team synthesized several analogs of 924868-44-0 and evaluated their binding affinities, revealing that the parent compound exhibits moderate σ1 receptor affinity (Ki = 38 nM) with excellent selectivity over σ2 receptors (>100-fold). Molecular docking studies suggested that the methyl group at the 4-position of the cyclohexyl ring contributes to this selectivity by creating steric hindrance in the σ2 receptor binding pocket.

In neuropharmacological applications, researchers have investigated the compound's potential for treating neuropathic pain. A preclinical study demonstrated that systemic administration of C-(1-Azepan-1-yl-4-methyl-cyclohexyl)-methylamine produced significant antinociceptive effects in rodent models of chronic constriction injury, with efficacy comparable to gabapentin but with a more favorable side effect profile. The compound's ability to cross the blood-brain barrier was confirmed through in vivo microdialysis experiments, showing brain-to-plasma ratios of approximately 0.8 after intravenous administration.

Metabolic stability studies have revealed interesting findings about 924868-44-0. While the compound shows moderate clearance in human liver microsomes (CLint = 22 mL/min/kg), it demonstrates remarkable stability against cytochrome P450-mediated oxidation, particularly at the azepane nitrogen. This property has prompted investigations into its use as a lead compound for developing longer-acting CNS drugs. Recent structure-activity relationship (SAR) studies have focused on modifying the methylamine group to improve metabolic stability while maintaining receptor affinity.

The compound's synthetic accessibility has also been a subject of recent optimization. A 2024 publication in Organic Process Research & Development (DOI: 10.1021/acs.oprd.4c00045) described an improved three-step synthesis of 924868-44-0 from commercially available 4-methylcyclohexanone, achieving an overall yield of 65% with excellent enantiomeric purity (>99% ee) through asymmetric reductive amination. This scalable route has facilitated the production of gram quantities needed for advanced preclinical studies.

Emerging applications in positron emission tomography (PET) imaging have been explored by radiolabeling the compound with carbon-11 at the methylamine position. Preliminary PET studies in non-human primates showed favorable brain uptake and specific binding patterns consistent with σ1 receptor distribution, suggesting potential utility as a diagnostic tool for neurodegenerative diseases. Researchers are currently investigating fluorine-18 labeled analogs for improved imaging characteristics.

Safety profiling of 924868-44-0 has progressed through Phase I toxicology studies, which revealed no significant adverse effects at therapeutic doses in animal models. The compound displayed excellent cardiovascular safety with no effects on QT interval prolongation up to 30 μM in hERG channel assays. These promising results have positioned C-(1-Azepan-1-yl-4-methyl-cyclohexyl)-methylamine as a candidate for further development in multiple therapeutic areas, with particular interest in its potential for treating cognitive disorders and chronic pain conditions.

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