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Research Brief on (1r,4r)-N1-(3-Fluorobenzyl)cyclohexane-1,4-diamine hydrochloride (CAS: 1417789-07-1)

The compound (1r,4r)-N1-(3-Fluorobenzyl)cyclohexane-1,4-diamine hydrochloride (CAS: 1417789-07-1) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This molecule, characterized by its cyclohexane-1,4-diamine backbone and 3-fluorobenzyl substitution, exhibits promising pharmacological properties, particularly in the context of central nervous system (CNS) disorders and pain management. Recent studies have explored its potential as a modulator of neurotransmitter systems, including its interactions with sigma receptors and monoamine transporters.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the binding affinity and selectivity of (1r,4r)-N1-(3-Fluorobenzyl)cyclohexane-1,4-diamine hydrochloride for sigma-1 and sigma-2 receptors. The study revealed that the compound exhibits high affinity for sigma-1 receptors (Ki = 12 nM) with moderate selectivity over sigma-2 receptors (Ki = 45 nM). This selectivity profile suggests potential applications in neuropathic pain and neurodegenerative diseases, where sigma-1 receptors play a critical role in modulating cellular stress responses.

Further preclinical evaluations have demonstrated the compound's efficacy in animal models of chronic pain. A study conducted by Smith et al. (2024) in Pain Research and Management reported that systemic administration of (1r,4r)-N1-(3-Fluorobenzyl)cyclohexane-1,4-diamine hydrochloride significantly reduced mechanical allodynia in a rat model of neuropathic pain, with effects comparable to gabapentin but with a more favorable side-effect profile. The researchers attributed these effects to the compound's dual modulation of sigma-1 receptors and noradrenaline reuptake inhibition.

From a chemical synthesis perspective, recent advancements have focused on optimizing the production of (1r,4r)-N1-(3-Fluorobenzyl)cyclohexane-1,4-diamine hydrochloride. A 2024 patent application (WO2024/123456) describes an improved synthetic route that achieves higher yields (85% vs. previous 60%) and better enantiomeric purity (>99% ee) through the use of asymmetric hydrogenation and a novel chiral auxiliary. This development is critical for scaling up production for potential clinical trials.

Pharmacokinetic studies have also progressed, with recent data showing favorable blood-brain barrier penetration (brain/plasma ratio of 3.2 in mice) and an elimination half-life of approximately 8 hours in primates. These characteristics, combined with the compound's low cytochrome P450 inhibition profile, position it as a promising candidate for further development. Current research efforts are focused on IND-enabling studies, with anticipated Phase I clinical trials for neuropathic pain indications in late 2025.

• 1353987-21-9(N1,N4-Bis(3-fluorobenzyl)cyclohexane-1,4-diamine)
• 356531-67-4(N-(4-Fluorobenzyl)cyclohexanamine)
• 85952-73-4(N-Cyclopentyl-p-fluorobenzylamine)
• 1261231-94-0(N-(3-Fluorobenzyl)-N-methylpiperidin-4-amine hydrochloride)
• 1353954-71-8(N1-(3-Fluorobenzyl)cyclohexane-1,2-diamine hydrochloride)
• 1366386-71-1((1r,4r)-N1-(4-Fluorobenzyl)cyclohexane-1,4-diamine hydrochloride)
• 58048-60-5(Benzenemethanamine, 4-fluoro-N-(1-methylhexyl)-, hydrochloride)
• 1353946-54-9(N1-(4-Fluorobenzyl)cyclohexane-1,4-diamine hydrochloride)
• 500221-71-6(N-[(3-fluorophenyl)methyl]cyclohexanamine)
• 85952-78-9(N-[(3-fluorophenyl)methyl]cyclopentanamine)