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    17692-51-2

    Catalog No. EBD226477

    CAS 17692-51-2

    Name 1,6-dimethyl-82-carbobenzyloxy-aminomethyl-10±-ergoline

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    Basic Information

    Synonyms: [[(82)-1,6-dimethylergolin-8-yl]-methyl]carbamicacidphenylmethylester Methergoline Metergoline

    Molecular Formula: C25H29N3O2

    Molecular Weight: 403.52

    MDL Number: MFCD00153829

    Categories: Medicinal Chemistry > APIs and Their Salts > Antineoplastic Agents Medicinal Chemistry > Biochemicals and Life Science Reagents > Phytochemicals and Natural Products

    Product Description:
    Metacrine is a synthetic derivative of the natural product emetine, an alkaloid originally isolated from the ipecacuanha plant. It is a potent and selective inhibitor of dihydroorotate dehydrogenase (DHODH), a key enzyme in the de novo pyrimidine biosynthesis pathway. This compound is characterized by its complex isoquinoline alkaloid structure. The primary and most significant application of Metacrine is in oncology research and development as a potential therapeutic agent for acute myeloid leukemia (AML). By inhibiting DHODH, it disrupts the production of nucleotides essential for rapidly proliferating cancer cells, leading to cell cycle arrest and apoptosis. Its selectivity and mechanism of action have made it a valuable tool compound for studying pyrimidine metabolism in cancer biology and a candidate for further drug development. Beyond its direct role as an investigational API, Metacrine serves as a key reference standard and a structurally interesting scaffold in medicinal chemistry. Its origin from a natural product template places it within the realm of bioactive natural product derivatives studied for their pharmacological potential.
    Physical Properties

    Melting Point: 148-150 °C(lit.)

    Boiling Point: 612.5 °C at 760 mmHg

    Flash Point: 324.2 °C

    Density: 1.25 g/cm3

    Solubility: 0.1 M HCl: 1.4 mg/mL

    Storage: −20°C

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