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1-(1-Phenylcyclohexyl)methanamine (CAS 17380-54-0): Structural, Pharmacological, and Research Perspectives

1-(1-Phenylcyclohexyl)methanamine, also known by its CAS number 17380-54-0, is a chemical compound with a complex molecular architecture that has garnered significant attention in pharmacological and biochemical research. Its IUPAC name, 1-(1-phenylcyclohexyl)methanamine, reflects its structural features: a cyclohexane ring substituted with a phenyl group and an amine moiety. This compound is part of the broader class of arylcycloalkylamines, which are characterized by their ability to interact with various neurotransmitter systems in the central nervous system (CNS). The molecular formula of 1-(1-phenylcyclohexyl)methanamine is C??H??N, with a molar mass of 243.36 g/mol. Its synthesis typically involves multi-step organic reactions, including Friedel-Crafts alkylation for the phenylation of cyclohexane and subsequent amine functionalization.

The pharmacological profile of CAS 17380-54-0 is primarily defined by its interaction with N-methyl-D-aspartate (NMDA) receptors, a key target in neuropharmacology. As an NMDA receptor antagonist, 1-(1-phenylcyclohexyl)methanamine modulates glutamatergic signaling, which plays a critical role in synaptic plasticity, memory formation, and neuroprotection. Recent studies have highlighted its potential as a tool compound for investigating glutamate receptor dynamics and their implications in neurological disorders such as Alzheimer’s disease and epilepsy. However, due to its complex mechanism of action involving multiple receptor systems—including sigma receptors and voltage-gated sodium channels—research on this compound remains focused on elucidating its dual role as both a research reagent and a model for understanding CNS pathophysiology.

In the context of modern drug discovery, compounds structurally related to 1-(1-phenylcyclohexyl)methanamine have inspired the development of novel therapeutics targeting psychiatric and neurodegenerative conditions. For instance, derivatives with modified substituents on the cyclohexane or phenyl rings have been explored for their potential to enhance selectivity toward specific receptor subtypes while minimizing off-target effects. A 2023 review in *Neuropharmacology* emphasized how computational modeling techniques are being employed to predict binding affinities between arylcycloalkylamines like CAS 17380-54-0 and their protein targets, accelerating the rational design of next-generation modulators.

The synthesis pathway for CAS 17380-54-0 involves several critical steps that require precise control over reaction conditions. The initial step typically employs Friedel-Crafts alkylation to attach a phenethyl group to cyclohexane under acidic catalysis. Subsequent reductive amination or alkylation processes introduce the terminal amine functionality essential for biological activity. Recent advancements in green chemistry have prompted researchers to optimize these syntheses using solvent-free conditions or biocatalytic approaches to improve yield and reduce environmental impact.

In terms of analytical characterization, nuclear magnetic resonance (NMR) spectroscopy is indispensable for confirming the structure of CAS 17380-54-0. The proton NMR spectrum exhibits distinct signals corresponding to aromatic protons from the phenyl ring (δ ~7–8 ppm), aliphatic protons from the cyclohexane ring (δ ~2–3 ppm), and the methylene protons adjacent to the amine group (δ ~2–2.5 ppm). Mass spectrometry further corroborates its molecular weight through characteristic fragmentation patterns observed during electron ionization (EI) or electrospray ionization (ESI) experiments.

Beyond its pharmacological relevance, compounds like CAS 17380-54-0 serve as valuable probes in mechanistic studies of receptor-ligand interactions. For example, radiolabeled derivatives have been utilized in positron emission tomography (PET) imaging to visualize NMDA receptor distribution in living organisms—a technique now being refined for early diagnosis of neurodegenerative diseases such as Parkinson’s disease.

The safety profile of CAS 17380-54-0 necessitates rigorous evaluation under controlled laboratory settings due to its potent biological activity at low concentrations. Current guidelines recommend handling this compound within fume hoods equipped with HEPA filtration systems when working with solutions exceeding micromolar ranges.

Ongoing research continues to expand our understanding of how subtle structural modifications can alter the pharmacodynamics of arylcycloalkylamines like CAS 17380-54-0. For instance, substituting hydrogen atoms on either ring system can significantly influence lipophilicity—a property directly linked to CNS penetration efficiency—and thus therapeutic efficacy versus toxicity profiles.

• 771582-88-8(1-(4-methylphenyl)cyclohexylmethylamine)
• 4442-89-1(2-cyclohexyl-2-phenylethanamine)
• 2287317-45-5([3-(4-Methylphenyl)-1-bicyclo[1.1.1]pentanyl]methanamine)
• 1039953-62-2({1-4-(propan-2-yl)phenylcyclobutyl}methanamine)
• 2287289-01-2(INDEX NAME NOT YET ASSIGNED)
• 17380-59-5((1-phenylcyclohexyl)methanamine hydrochloride)
• 1094477-12-9(1-[1-(3-methylphenyl)cyclohexyl]methanamine)
• 1096853-40-5(1-(4-tert-butylphenyl)cyclobutylmethanamine)
• 117077-68-6(Tricyclo[3.3.1.13,7]decane-1-methanamine, 3-(4-methylphenyl)-)
• 91245-59-9((1-phenylcyclobutyl)methanamine)