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• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Aralkylamines
• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Amines Aralkylamines

Research Briefing on (S)-1-Cyclopropyl-1-phenylmethanamine (CAS: 321863-61-0) in Chemical Biology and Pharmaceutical Applications

(S)-1-Cyclopropyl-1-phenylmethanamine (CAS: 321863-61-0) has emerged as a chiral building block of significant interest in medicinal chemistry and drug discovery. Recent studies highlight its structural versatility as a privileged scaffold for developing CNS-active compounds, particularly due to the cyclopropyl moiety's ability to confer metabolic stability while maintaining conformational flexibility. The stereospecific (S)-configuration at the chiral center has shown enhanced binding affinity in several target systems compared to its (R)-enantiomer.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's utility as a key intermediate in synthesizing novel κ-opioid receptor antagonists. Researchers at Kyoto University developed an optimized synthetic route starting from (S)-1-cyclopropyl-1-phenylmethanamine, achieving 92% enantiomeric purity through asymmetric hydrogenation. The resulting derivatives exhibited sub-nanomolar binding affinity (Ki = 0.78 nM) with improved metabolic stability in human liver microsomes (t_1/2 > 120 min).

In neuropharmacology applications, a Nature Communications paper (2024) reported the compound's incorporation into positive allosteric modulators of α7 nicotinic acetylcholine receptors. The cyclopropyl group was found to reduce P-glycoprotein efflux by 40% compared to linear alkyl analogs, significantly enhancing blood-brain barrier penetration (brain/plasma ratio = 2.1). This property makes (S)-1-cyclopropyl-1-phenylmethanamine particularly valuable for CNS drug development.

Recent ADMET studies (European Journal of Pharmaceutical Sciences, 2024) revealed that derivatives maintain favorable pharmacokinetic profiles, with oral bioavailability ranging 65-78% in rodent models. The cyclopropylamine moiety demonstrates remarkable resistance to CYP450-mediated oxidation, addressing a common metabolic vulnerability in similar scaffolds. Quantum mechanical calculations suggest this stability arises from the ring strain energy (≈27.5 kcal/mol) that disfavors oxidative ring opening.

Ongoing clinical trials (Phase Ib) by Vertex Pharmaceuticals feature a hepatitis C virus NS5A inhibitor incorporating this chiral amine, where it contributes to pan-genotypic activity (EC₅₀ = 0.3-1.2 nM across genotypes 1-6). The compound's synthetic accessibility - now achievable in 3 steps from commercially available (S)-phenylglycinol - positions it as a cost-effective option for large-scale production, with recent process chemistry improvements yielding >85% overall yield.

Emerging applications in radiopharmaceuticals have been reported at the 2024 SNMMI Annual Meeting, where ¹⁸F-labeled derivatives showed promising results as PET tracers for imaging neuroinflammation. The rigid cyclopropyl structure minimized non-specific binding while maintaining target engagement, with a 3.5-fold increase in signal-to-noise ratio compared to previous generation tracers.

• 56640-53-0(2-Methyl-1-phenyl-butylamine)
• 681509-99-9(Benzenemethanamine, a-(cyclopropylmethyl)-)
• 23459-38-3(1-Cyclopropyl-1-phenylmethanamine)
• 535925-71-4(cyclopropyl(4-methylphenyl)methanamine)
• 140167-41-5(Cyclopropyl(4-propylphenyl)methanamine)
• 434307-26-3((R)-Cyclopropyl(phenyl)methanamine)
• 844470-80-0((1S)-Cyclopropylphenylmethylamine Hydrochloride)
• 535925-72-5(Cyclopropyl-(3-methylphenyl)methanamine)
• 1416450-04-8((R)-cyclopropyl(phenyl)methanamine hydrochloride)
• 39959-72-3(cyclopropyl(phenyl)methanamine;hydrochloride)