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World Anti-Doping Agency prohibited substances
7-Keto-DHEA
Другие языки:

    7-Keto-DHEA

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    7-Keto-DHEA
    7-Keto-DHEA.svg
    7-Keto-DHEA
    7-Keto-DHEA acetate.svg
    7-Keto-DHEA acetate
    Names
    IUPAC name
    3β-Hydroxyandrost-5-ene-7,17-dione
    Systematic IUPAC name
    (3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-Dimethyl-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthrene-1,4(3bH)-dione
    Other names
    7-Oxo-DHEA; 7-Ketodehydroepiandrosterone; 7-Oxodehydroepiandrosterone; 3β-Hydroxyandrost-5-ene-7,17-dione; Androst-5-en-3β-ol-7,17-dione
    Identifiers
    3D model (JSmol)
    ChEBI
    ChemSpider
    PubChem CID
    UNII
    • InChI=1S/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/m0/s1
      Key: KPRGOTLNGIBVFL-GINZOMEDSA-N
    • InChI=1/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/m0/s1
      Key: KPRGOTLNGIBVFL-GINZOMEDBE
    • O=C2\C=C4/[C@]([C@H]3CC[C@@]1(C(=O)CC[C@H]1[C@H]23)C)(C)CC[C@H](O)C4
    Properties
    C19H26O3
    Molar mass 302.414 g·mol−1
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    7-Ketodehydroepiandrosterone (7-keto-DHEA,7-oxo-DHEA), also known as 7-oxoprasterone, is a prohormone produced by metabolism of the prohormone dehydroepiandrosterone (DHEA).

    7-oxo-DHEA is even more effective than DHEA for inducing heat production (thermogenesis). Because dieting is usually accompanied by reduced resting metabolic rate, obese persons may benefit from using 7-oxo-DHEA when dieting due to increased metabolic rate.

    7-Keto-DHEA is not directly converted to testosterone or estrogen, and has thus been investigated as a potentially more useful relative of DHEA. Researchers have raised concern that supplements may trigger positive tests for performance-enhancing drugs.

    The World Anti-Doping Agency lists 7-keto-DHEA as a prohibited anabolic agent. The FDA has proposed that it be banned from use in compounded drugs.

    Chemistry

    7-Keto-DHEA has a number of chemical names, including:

    • 7-Ketodehydroepiandrosterone (7-keto-DHEA)
    • 7-Oxodehydroepiandrosterone (7-oxo-DHEA)
    • 7-Ketoprasterone
    • 7-Oxoprasterone
    • 3β-Hydroxyandrost-5-ene-7,17-dione
    • Androst-5-en-3β-ol-7,17-dione

    For the acetate ester:

    • 3β-Acetoxyandrost-5-ene-7,17-dione
    • 7-Oxo-dehydroepiandrosterone acetate (7-oxo-DHEA acetate)
    • 3-Acetyl-7-oxo-dehydroepiandrosterone (3-acetyl-7-oxo-DHEA)
    • DHEA acetate-7-one
    • Δ5-Androstene-3β-acetoxy-7,17-dione

    Note: "Keto" can be substituted for "oxo" in the above names.

    History

    7-Keto-DHEA has been marketed by alternative medicine providers as a treatment of Adrenal fatigue, a pseudo-scientific term with no scientific basis.

    Regulation

    The FDA has proposed that 7-Keto-DHEA be included among substances banned from use in compounded drugs.

    See also


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