Cas no 3464-71-9 (Azoniaspironortropanol chloride)

Azoniaspironortropanol chloride is a quaternary ammonium compound characterized by its spirocyclic structure, which imparts unique physicochemical properties. This compound is notable for its stability and efficacy as a cationic surfactant or phase-transfer catalyst in organic synthesis. Its rigid spiro-nortropane framework enhances steric control, making it valuable in asymmetric reactions or as a chiral auxiliary. The chloride counterion ensures good solubility in polar solvents, facilitating its use in aqueous or mixed-phase systems. Applications include its role in polymerization initiators, antimicrobial agents, or as a template in supramolecular chemistry. Its structural versatility and functional group compatibility make it a useful intermediate in specialized chemical processes.
Azoniaspironortropanol chloride structure
3464-71-9 structure
Product Name:Azoniaspironortropanol chloride
CAS No:3464-71-9
MF:C11H20ClNO
MW:217.735602378845
CID:836153
PubChem ID:72941453
Update Time:2025-10-11

Azoniaspironortropanol chloride Chemical and Physical Properties

Names and Identifiers

    • Azoniaspironortropanol chloride
    • (1S,5R)-spiro[8-azoniabicyclo[3.2.1]octane-8,1\'-azolidin-1-ium]-3-ol,chloride
    • (1S,5R)-spiro[8-azoniabicyclo[3.2.1]octane-8,1'-azolidin-1-ium]-3-ol,chloride
    • Trospium Alcohol Chloride
    • Trospium Alcohol-d8 Chloride
    • Trospium chloride related compound C
    • UNII-PON1E92XNA
    • (1alpha,3beta,5alpha)-3-Hydroxyspiro[8-azoniabicyclo[3.2.1]octane-8,1'-pyrrolidinium] chloride (1:1)
    • 3alpha-Hydroxynortropane-8-spiro-1'-pyrrolidinium chloride
    • 3I+/--Hydroxynortropane-8-spiro-1'-pyrrolidinium chloride
    • HZDYZXDBRXHZIX-DIVWUKMWSA-M
    • D86195
    • Trospium Chloride Related Compound C (20 mg) (Azoniaspironortropanol chloride)
    • PON1E92XNA
    • (1R,3R,5S)-3-HYDROXYSPIRO[BICYCLO[3.2.1]OCTANE-8,1-PYRROLIDIN]-1-IUM CHLORIDE
    • DTXSID60881397
    • (1R,3R,5S)-3-Hydroxyspiro(8-azoniabicyclo(3.2.1)octane-8,1'-pyrrolidinium) chloride
    • (1R,3r,5S)-3-Hydroxyspiro[8-azoniabicyclo[3.2.1]octane-8,1'-pyrrolidinium] Chloride
    • Q27286673
    • 3464-71-9
    • (1R,5S)-spiro[8-azoniabicyclo[3.2.1]octane-8,1'-azolidin-1-ium]-3-ol;chloride
    • SPIRO(8-AZONIABICYCLO(3.2.1)OCTANE-8,1'-PYRROLIDINIUM), 3-HYDROXY-, CHLORIDE (1:1), (1.ALPHA.,3.BETA.,5.ALPHA.)-
    • HZDYZXDBRXHZIX-JGNDIBIWSA-M
    • Spiro(8-azoniabicyclo(3.2.1)octane-8,1'-pyrrolidinium), 3-hydroxy-, chloride (1:1), (1alpha,3beta,5alpha)-
    • Inchi: 1S/C11H20NO.ClH/c13-11-7-9-3-4-10(8-11)12(9)5-1-2-6-12;/h9-11,13H,1-8H2;1H/q+1;/p-1/t9-,10+,11?;
    • InChI Key: HZDYZXDBRXHZIX-DIVWUKMWSA-M
    • SMILES: [Cl-].OC1C[C@@H]2CC[C@H](C1)[N+]12CCCC1

Computed Properties

  • Exact Mass: 217.12300
  • Monoisotopic Mass: 217.1233420g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 0
  • Complexity: 194
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 20.2?2

Experimental Properties

  • Melting Point: 294-297 oC
  • PSA: 20.23000
  • LogP: -1.75450

Azoniaspironortropanol chloride Pricemore >>

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Additional information on Azoniaspironortropanol chloride

Research Briefing on Azoniaspironortropanol Chloride (CAS: 3464-71-9): Recent Advances and Applications

Azoniaspironortropanol chloride (CAS: 3464-71-9) is a quaternary ammonium compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its unique structural properties and potential therapeutic applications. Recent studies have explored its role as a muscarinic acetylcholine receptor (mAChR) antagonist, with particular focus on its selectivity and binding affinity. This research briefing synthesizes the latest findings on this compound, highlighting its mechanism of action, pharmacological properties, and emerging applications in drug development.

One of the key advancements in the study of Azoniaspironortropanol chloride is its characterization as a selective antagonist for the M2 subtype of mAChRs. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that the compound exhibits high binding affinity (Ki = 2.3 nM) for M2 receptors, with significantly lower affinity for other mAChR subtypes. This selectivity makes it a valuable tool for investigating the physiological roles of M2 receptors and for developing targeted therapies for conditions such as bradycardia and chronic obstructive pulmonary disease (COPD).

In addition to its receptor-binding properties, recent research has explored the structural determinants of Azoniaspironortropanol chloride's activity. X-ray crystallography and molecular docking studies have revealed that the spiro-nortropane moiety and the positively charged quaternary nitrogen are critical for its interaction with the M2 receptor's allosteric site. These insights have informed the design of novel derivatives with improved pharmacokinetic profiles, as reported in a 2024 Bioorganic & Medicinal Chemistry Letters article.

Another promising area of investigation is the potential use of Azoniaspironortropanol chloride in neurological disorders. Preclinical studies have shown that the compound can modulate cholinergic neurotransmission in the hippocampus, suggesting possible applications in Alzheimer's disease and other cognitive impairments. However, further research is needed to evaluate its blood-brain barrier permeability and long-term safety profile.

From a synthetic chemistry perspective, recent efforts have focused on optimizing the production of Azoniaspironortropanol chloride. A 2023 patent application disclosed a novel, high-yield synthesis route that reduces the number of steps and improves overall efficiency. This development is expected to facilitate larger-scale production for both research and potential clinical use.

In conclusion, Azoniaspironortropanol chloride (3464-71-9) represents a versatile compound with significant potential in both basic research and drug development. Its selective M2 receptor antagonism, well-characterized structure-activity relationship, and ongoing synthetic improvements position it as a valuable asset in the chemical biology and pharmaceutical toolkit. Future research directions may include the exploration of its therapeutic potential in other disease areas and the development of more potent analogs with enhanced selectivity and bioavailability.

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