Cas no 29913-84-6 (S-Methyl-D-penicillamine)

S-Methyl-D-penicillamine is a chiral thiol compound derived from penicillamine, featuring a methylated sulfhydryl group. This modification enhances its stability and alters its reactivity compared to the parent molecule. It is primarily utilized in research applications, particularly in studies involving metal chelation, enzyme inhibition, and as a precursor in organic synthesis. The D-configuration ensures stereochemical specificity, making it valuable for investigating chiral interactions in biological systems. Its ability to form stable complexes with heavy metals also lends utility in detoxification research. The compound’s well-defined structure and purity make it a reliable tool for mechanistic studies in biochemistry and medicinal chemistry.
S-Methyl-D-penicillamine structure
S-Methyl-D-penicillamine structure
Product Name:S-Methyl-D-penicillamine
CAS No:29913-84-6
MF:C6H13NO2S
MW:163.23792052269
CID:289739
PubChem ID:10329618
Update Time:2025-11-07

S-Methyl-D-penicillamine Chemical and Physical Properties

Names and Identifiers

    • D-Valine,3-(methylthio)-
    • S-Methyl-D-penicillamine
    • (2S)-2-amino-3-methyl-3-methylsulfanylbutanoic acid
    • S-Methylpenicillamine
    • Valine,3-(methylthio)-, D- (8CI)
    • (2S)-2-amino-3-methyl-3-(methylsulfanyl)butanoic acid
    • SCHEMBL7418366
    • CHEMBL3544554
    • DTXSID50184026
    • XSMLYGQTOGLZDA-BYPYZUCNSA-N
    • D-Valine, 3-(methylthio)-
    • 29913-84-6
    • J-017687
    • DB-231774
    • 3-(Methylthio)-D-valine; S-Methylpenicillamine;
    • (S)-2-Amino-3-methyl-3-(methylthio)butanoic acid
    • Inchi: 1S/C6H13NO2S/c1-6(2,10-3)4(7)5(8)9/h4H,7H2,1-3H3,(H,8,9)/t4-/m0/s1
    • InChI Key: XSMLYGQTOGLZDA-BYPYZUCNSA-N
    • SMILES: S(C)C(C)(C)[C@H](C(=O)O)N

Computed Properties

  • Exact Mass: 163.06679
  • Monoisotopic Mass: 163.06669983g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 3
  • Complexity: 136
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.1
  • Topological Polar Surface Area: 88.6?2

Experimental Properties

  • Density: 1.2±0.1 g/cm3
  • Boiling Point: 278.5±35.0 °C at 760 mmHg
  • Flash Point: 122.3±25.9 °C
  • PSA: 63.32
  • Vapor Pressure: 0.0±1.2 mmHg at 25°C

S-Methyl-D-penicillamine Security Information

S-Methyl-D-penicillamine Pricemore >>

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Additional information on S-Methyl-D-penicillamine

Recent Advances in the Study of S-Methyl-D-penicillamine (CAS: 29913-84-6)

S-Methyl-D-penicillamine (CAS: 29913-84-6) is a derivative of penicillamine, a well-known chelating agent and therapeutic compound used in the treatment of Wilson's disease and rheumatoid arthritis. Recent studies have explored its potential applications in various biomedical fields, including its role as an antioxidant, metal chelator, and modulator of enzymatic activity. This research brief synthesizes the latest findings on S-Methyl-D-penicillamine, focusing on its chemical properties, biological activities, and therapeutic potential.

One of the key areas of interest in recent research is the compound's ability to modulate oxidative stress. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that S-Methyl-D-penicillamine exhibits significant antioxidant properties, effectively scavenging reactive oxygen species (ROS) in vitro. The study highlighted its potential as a therapeutic agent for diseases characterized by oxidative damage, such as neurodegenerative disorders and cardiovascular diseases. The researchers utilized advanced spectroscopic techniques to elucidate the mechanism of action, revealing that the compound's thiol group plays a critical role in its antioxidant activity.

Another significant development is the exploration of S-Methyl-D-penicillamine's chelating properties. A recent paper in Bioinorganic Chemistry and Applications investigated its efficacy in binding heavy metals, particularly copper and mercury. The study found that S-Methyl-D-penicillamine forms stable complexes with these metals, suggesting its utility in detoxification therapies. The researchers also compared its chelating efficiency with other penicillamine derivatives, noting that the methyl substitution enhances its stability and bioavailability.

In addition to its antioxidant and chelating properties, S-Methyl-D-penicillamine has been studied for its potential role in modulating enzymatic activity. A 2024 study in Biochemical Pharmacology explored its effects on matrix metalloproteinases (MMPs), enzymes implicated in tissue remodeling and inflammatory diseases. The findings indicated that S-Methyl-D-penicillamine can inhibit specific MMPs, offering a novel approach to treating conditions like arthritis and fibrosis. The study employed molecular docking simulations and enzyme kinetics assays to validate these effects.

Despite these promising findings, challenges remain in the clinical translation of S-Methyl-D-penicillamine. Pharmacokinetic studies, as reported in a 2023 review in Drug Metabolism Reviews, indicate that the compound's oral bioavailability is limited, necessitating the development of improved formulations or delivery systems. Additionally, further in vivo studies are required to assess its safety and efficacy in animal models before progressing to human trials.

In conclusion, recent research on S-Methyl-D-penicillamine (CAS: 29913-84-6) underscores its multifaceted potential in biomedicine. Its antioxidant, chelating, and enzyme-modulating properties make it a promising candidate for therapeutic development. However, addressing its pharmacokinetic limitations and conducting comprehensive preclinical studies will be crucial for advancing its clinical applications. Future research should focus on optimizing its formulation and exploring its synergistic effects with other therapeutic agents.

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