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Steroids2b Javier, Dan, Alex, Gwenael

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  • 1. To or not to “ Juice” “ Juice” ? Supplemental Testosterone in Sports Javier Amigon Daniel Ho Alex Lukatskiy Gwenael Gatto By:
  • 2.
    • Testosterone is a naturally occurring steroid.
    Background Testosterone
    • Androgenic effects
      • -Male secondary sex characteristics
    • Anabolic Effects
    • Medical Use
    2 3 4 5 1 0 1 6 7 8 9 1 4 1 3 1 2 1 1 1 5 1 6 1 7 O 1 9 H 1 8 O H 2 2 H H H 2 5 A B C D
  • 3. Schematic Representation of Intermolecular Interactions between Testosterone and Amino Acids in the Ligand Binding Domain of the Androgen Receptor Testosterone in the Androgen Receptor Hydrogen Bonding
  • 4. Schematic Representation of Intermolecular Interactions between Testosterone and Amino Acids in the Ligand Binding Domain of the Androgen Receptor Testosterone in the Androgen Receptor Van der Waals Forces
  • 5. Cell Membrane Nucleus Cytoplasm Muscle Growth DNA Biological Mechanism of Testosterone T T A
  • 6.  
  • 7.
    • Testosterone banned (1991, Controlled Substances Act)
    Testosterone is Banned in Sports
    • Dietary supplements
    • Emergence of testosterone precursors.
    • Ex. Androstenedione (“Andro”) -1998
  • 8. Testosterone in Sports
    • Athlete’s desire to improve athletic performance.
    • Supplemental testosterone via injections, pills or topical creams.
    Floyd Landis- Tour de France Mark McGwire –Major League Baseball Notable Athletes:
  • 9. Synthesis of Androstenedione Corticosterone Keto-Enol Tautomerization 1. Na + - OCH 3 o o 2. O H O H O O H O H H O
  • 10. Synthesis of Androstenedione (cont.) Androstenedione + + . . . . . . . . . . -
  • 11. Proton NMR Spectroscopy H H H H H H Androstenedione O O (s, 6H)
  • 12. Testosterone Proton NMR Spectroscopy H H H H H H H
    • Electron donating effects of oxygen.
    • Neighboring protons more shielded.
    (S,1H) (t,1H) (s,3H) (s,3H)
  • 13. Androstenedione IR Spectroscopy
  • 14. Testosterone IR Spectroscopy
  • 15. Does Androstenedione Make You Stronger?
    • Increases estrone and estradiol levels in men
    Androstenedione Aromatase Testosterone Estradiol Aromatase Estrone The Result?
  • 16. Man Boobs! (aka Gynecomastia)
  • 17. Conclusions
    • Desired results not achieved.
    • Other methods to bypass laws.
    • Designer Steroids
    • - BALCO, Olympics
    • How to stay ahead of designer steroid manufacturers?
  • 18. References Floyd Landis: http://www.roadcycling.com/artman/uploads/5_landis_podium_002.jpg Mark McGwire: http://www.misunderestimation.com/wp-content/uploads/2007/01/GotJuice.jpg Homer Simpson: http://users. bigpond .net.au/ simpsons /mirror. jpg Health Effects of Androstenedione. FDA White Paper. U.S. Food and Drug Administration. Retrieved on 4/13/09. http://www.fda.gov/oc/whitepapers/andro.html. FDA Warning on Androstenedione (Andro). National Center for Complementary and Alternative Medicine. Retrieved on 4/24/09. http://nccam.nih.gov/news/alerts/androstenedione/consumeradvisory.htm. Koert , Willem and Aede de Groot. The Anabolics Book. Retrieved on 4/10/09. http://www.ergogenics.org/anabolenboek/index21en.html. Yesalis, Charles E. (1999). Medical, Legal, and Societal Implications of Androstenedione Use. JAMA . 1999;281(21):2043-2044. Leder et al. (2002). Effects of Oral Androstenedione Administration on Serum Testosterone and Estradiol Levels in Postmenopausal Women. The Journal of Clinical Endocrinology & Metabolism 87(12):5449–5454. Cawley et al. The detection of androstenedione abuse in sport: a mass spectrometry strategy to identify the 4-hydroxyandrostenedione metabolite. Rapid Commun. Mass Spectrom. 2008; 22: 4147–4157. Le Pera et al (2003). A straightforward chemical synthesis of 17-ketosteroids by cleavage of the C-17-dihydroxyacetone Side chain in corticosteroids. Steroids 68 (2003) 139–142.