Cas no 932706-27-9 ((1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride)

(1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride is a chiral fluorinated cyclopentylamine derivative, commonly employed as a versatile intermediate in pharmaceutical synthesis and medicinal chemistry. Its stereospecific configuration (1S,2R) and fluorine substitution enhance its utility in the design of bioactive molecules, particularly for modulating receptor interactions or improving metabolic stability. The hydrochloride salt form ensures improved solubility and handling characteristics. This compound is valued for its potential applications in the development of CNS-targeting drugs, enzyme inhibitors, or peptidomimetics. Its rigid cyclopentane backbone and fluorine atom contribute to conformational restraint and electronic effects, making it a valuable building block for structure-activity relationship studies.
(1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride structure
932706-27-9 structure
Product Name:(1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride
CAS No:932706-27-9
MF:C5H11ClFN
MW:139.598943948746
MDL:MFCD19215170
CID:4665960
PubChem ID:55285365
Update Time:2025-06-27

(1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride Chemical and Physical Properties

Names and Identifiers

    • (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride
    • (1S,2R)-2-fluorocyclopentan-1-amine;hydrochloride
    • MDL: MFCD19215170
    • Inchi: 1S/C5H10FN.ClH/c6-4-2-1-3-5(4)7;/h4-5H,1-3,7H2;1H/t4-,5+;/m1./s1
    • InChI Key: ZJXOEOALNHXCOE-JBUOLDKXSA-N
    • SMILES: Cl.F[C@@H]1CCC[C@@H]1N

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 0
  • Complexity: 65.099
  • Topological Polar Surface Area: 26

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Additional information on (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride

Recent Advances in the Study of (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride (CAS: 932706-27-9)

In recent years, (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride (CAS: 932706-27-9) has emerged as a compound of significant interest in the field of chemical biology and medicinal chemistry. This chiral fluorinated cyclopentylamine derivative has shown promising potential in various therapeutic applications, particularly in the development of novel central nervous system (CNS) drugs. The unique structural features of this compound, including its stereochemistry and fluorine substitution, contribute to its distinctive pharmacological properties and metabolic stability.

Recent studies have focused on the synthetic methodologies for (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride, with particular emphasis on asymmetric synthesis routes that ensure high enantiomeric purity. A 2023 publication in the Journal of Medicinal Chemistry demonstrated an improved synthetic pathway using chiral auxiliaries, achieving >99% ee with significantly reduced production costs. This advancement is particularly important for scaling up production while maintaining the compound's pharmacological integrity.

The pharmacological profile of (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride has been extensively investigated in recent preclinical studies. Research published in Neuropharmacology (2024) revealed its potent activity as a selective serotonin reuptake inhibitor (SSRI) with additional noradrenergic effects, suggesting potential applications in treatment-resistant depression. The fluorine atom at the 2-position appears to enhance blood-brain barrier penetration while reducing metabolic degradation, leading to improved pharmacokinetic properties compared to non-fluorinated analogs.

Structural-activity relationship (SAR) studies have provided valuable insights into the molecular interactions of (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride with biological targets. X-ray crystallography data (Nature Structural Biology, 2023) demonstrated how the specific stereochemistry of the compound facilitates optimal binding to the serotonin transporter protein, explaining its enhanced selectivity. These findings are guiding the design of next-generation antidepressants with improved efficacy and reduced side effects.

Recent toxicological evaluations (Regulatory Toxicology and Pharmacology, 2024) have established a favorable safety profile for (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride in animal models. The studies reported no significant genotoxicity or cardiotoxicity at therapeutic doses, with a wide safety margin. These results support the compound's progression to clinical trials, with Phase I studies expected to begin in late 2024.

The pharmaceutical industry has shown growing interest in (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride as a potential lead compound. Several patent applications filed in 2023-2024 describe its use in combination therapies for neuropsychiatric disorders and as a molecular scaffold for developing new psychotropic agents. The compound's versatility is further highlighted by its investigation in other therapeutic areas, including neuropathic pain management and cognitive enhancement.

Future research directions for (1S,2R)-2-Fluorocyclopentan-1-amine hydrochloride include exploring its potential in personalized medicine approaches, particularly in patients with specific genetic polymorphisms affecting drug metabolism. Additionally, novel formulation strategies are being developed to optimize its delivery to target tissues while minimizing systemic exposure. The continued investigation of this compound represents an important frontier in CNS drug development and fluorinated pharmaceutical chemistry.

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