Cas no 1159977-52-2 (Naratriptan N-Oxide)

Naratriptan N-Oxide is a metabolite of naratriptan, a selective serotonin receptor agonist used in the treatment of migraines. This compound is of interest in pharmacokinetic and metabolic studies due to its role in understanding the biotransformation pathways of naratriptan. Its synthesis and characterization are valuable for analytical reference standards in clinical and forensic toxicology. Naratriptan N-Oxide exhibits high purity and stability, making it suitable for research applications, including drug metabolism investigations and the development of sensitive detection methods. Its well-defined structure ensures reliability in studies aimed at elucidating the pharmacological and toxicological profiles of naratriptan-related compounds.
Naratriptan N-Oxide structure
Naratriptan N-Oxide structure
Product Name:Naratriptan N-Oxide
CAS No:1159977-52-2
MF:C17H25N3O3S
MW:351.463702917099
CID:1062836
PubChem ID:46782454
Update Time:2025-10-30

Naratriptan N-Oxide Chemical and Physical Properties

Names and Identifiers

    • Naratriptan N-Oxide
    • N-methyl-2-[3-(1-methyl-1-oxidopiperidin-1-ium-4-yl)-1H-indol-5-yl]ethanesulfonamide
    • N-Nethyl-3-(1-methyl-1-oxido-4-piperidinyl)-1H-indole-5-ethanesulfonamide;
    • 1159977-52-2
    • N-Methyl-2-[3-(1-methyl-1-oxo-1lambda~5~-piperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide
    • DTXSID40676061
    • Inchi: 1S/C17H25N3O3S/c1-18-24(22,23)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2,21)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3
    • InChI Key: CIRYHRZTATXPEQ-UHFFFAOYSA-N
    • SMILES: S(CCC1C=CC2=C(C=1)C(=CN2)C1CC[N+](C)(CC1)[O-])(NC)(=O)=O

Computed Properties

  • Exact Mass: 351.16166284g/mol
  • Monoisotopic Mass: 351.16166284g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 24
  • Rotatable Bond Count: 5
  • Complexity: 526
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.4
  • Topological Polar Surface Area: 88.4?2

Naratriptan N-Oxide Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
N378740-1mg
Naratriptan N-Oxide
1159977-52-2
1mg
$ 219.00 2023-09-06
TRC
N378740-10mg
Naratriptan N-Oxide
1159977-52-2
10mg
$ 1681.00 2023-09-06
A2B Chem LLC
AE14800-1mg
Naratriptan N-Oxide
1159977-52-2
1mg
$318.00 2024-01-04
A2B Chem LLC
AE14800-10mg
Naratriptan N-Oxide
1159977-52-2
10mg
$1633.00 2024-01-04

Additional information on Naratriptan N-Oxide

Introduction to Naratriptan N-Oxide (CAS No. 1159977-52-2)

Naratriptan N-Oxide, chemically designated as (S)-4-[(1,3-dihydro-1-methyl-5-oxo-4-pyrimidinyl)methyl]-N,N-dimethyl-2-pyrrolidinamine N-oxide, is a significant derivative in the field of pharmaceutical chemistry. This compound, identified by its unique CAS No. 1159977-52-2, has garnered considerable attention due to its structural and pharmacological properties. The inclusion of an N-oxide group in its molecular structure imparts distinct characteristics that influence its biological activity and potential therapeutic applications.

The synthesis and characterization of Naratriptan N-Oxide have been subjects of extensive research, particularly in the context of developing novel therapeutic agents for the treatment of migraine and other neurological disorders. The compound belongs to the triptan class of drugs, which are known for their selective serotonin receptor (5-HT1B/1D) agonist properties. This class of medications has revolutionized the management of acute migraine attacks, providing effective relief with fewer side effects compared to older treatments.

Recent studies have highlighted the importance of metabolites and derivatives in optimizing drug efficacy and safety profiles. Naratriptan N-Oxide, as a metabolite of Naratriptan, has been investigated for its potential role in enhancing the pharmacokinetic properties of the parent compound. Research indicates that the N-oxide moiety can influence metabolic pathways, potentially leading to improved bioavailability and reduced toxicity. This has opened new avenues for drug development, particularly in formulations designed for targeted delivery and sustained release.

The structural modification introduced by the N-oxide group in Naratriptan N-Oxide also affects its interaction with biological targets. Computational modeling and experimental studies have demonstrated that this derivative exhibits enhanced binding affinity to 5-HT1B/1D receptors compared to Naratriptan itself. This improved binding affinity translates to more potent pharmacological effects, making Naratriptan N-Oxide a promising candidate for therapeutic intervention.

In addition to its pharmacological significance, Naratriptan N-Oxide has been studied for its potential role in drug-drug interactions. The unique chemical properties of this compound allow it to interact with various metabolic enzymes, which can be leveraged to develop combination therapies that enhance therapeutic outcomes while minimizing adverse effects. This aspect is particularly relevant in the context of polypharmacy, where patients often require multiple medications simultaneously.

The development of Naratriptan N-Oxide also underscores the importance of green chemistry principles in pharmaceutical synthesis. Efforts have been made to optimize synthetic routes that minimize waste and energy consumption, aligning with global initiatives to promote sustainable practices in drug manufacturing. These advancements not only contribute to environmental conservation but also enhance cost-effectiveness and scalability in production.

From a regulatory perspective, Naratriptan N-Oxide has undergone rigorous testing to ensure compliance with safety and efficacy standards set by global health authorities. Preclinical studies have provided valuable insights into its mechanism of action, pharmacokinetics, and potential side effects. These findings have been instrumental in guiding clinical trial design and ensuring that patients receive safe and effective treatments.

The clinical application of Naratriptan N-Oxide is still under exploration, but preliminary results are promising. Studies suggest that this derivative could offer a more refined approach to migraine management by providing targeted relief with fewer systemic side effects. As research progresses, additional therapeutic applications may be uncovered, further solidifying the compound's role in modern medicine.

In conclusion, Naratriptan N-Oxide (CAS No. 1159977-52-2) represents a significant advancement in pharmaceutical chemistry. Its unique structural features and pharmacological properties make it a valuable asset in the development of novel treatments for neurological disorders. With ongoing research efforts focused on optimizing its synthesis, efficacy, and safety profiles, this compound is poised to make a substantial impact on patient care in the coming years.

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