Presentation

1. To or not to “ Juice” “ Juice” ? Supplemental Testosterone in Sports Javier Amigon Daniel Ho Alex Lukatskiy Gwenael Gatto By:

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

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)

13. Androstenedione IR Spectroscopy

14. Testosterone IR Spectroscopy

16. Man Boobs! (aka Gynecomastia)

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.