steroids2b javier, dan, alex, gwenael
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ToTo or not toor not to“Juice”“Juice” “Juice”“Juice”
Javier AmigonDaniel HoAlex LukatskiyGwenael Gatto
Javier AmigonDaniel HoAlex LukatskiyGwenael Gatto
By:By:
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Supplemental Testosterone in SportsSupplemental Testosterone in Sports
Testosterone is a naturally occurring steroid.
Testosterone is a naturally occurring steroid.
BackgroundBackground
2
3
4
5
10
1
6
7
8
9 14
13
12
11
15
16
17
O
19H
18 OH22
HH
H 25
AB
CD
TestosteroneTestosterone
Androgenic effects
-Male secondary sex characteristics
Androgenic effects
-Male secondary sex characteristics
Anabolic Effects Anabolic Effects
Medical Use Medical Use
Schematic Representation of Intermolecular Interactions between Testosterone and Amino Acids in the Ligand Binding Domain of the Androgen ReceptorSchematic Representation of Intermolecular Interactions between Testosterone and Amino Acids in the Ligand Binding Domain of the Androgen Receptor
Hydrogen Bonding
Testosterone in the Androgen ReceptorTestosterone in the Androgen Receptor
Schematic Representation of Intermolecular Interactions between Testosterone and Amino Acids in the Ligand Binding Domain of the Androgen ReceptorSchematic Representation of Intermolecular Interactions between Testosterone and Amino Acids in the Ligand Binding Domain of the Androgen Receptor
Van der WaalsForces
Testosterone in the Androgen ReceptorTestosterone in the Androgen Receptor
T
Cell MembraneCell Membrane NucleusNucleusCytoplasmCytoplasm
T A Muscle Growth Muscle Growth
DNADNA
Biological Mechanism of TestosteroneBiological Mechanism of Testosterone
Testosterone banned (1991, Controlled Substances Act) Testosterone banned (1991, Controlled Substances Act)
Testosterone is Banned in SportsTestosterone is Banned in Sports
Emergence of testosterone precursors.
Ex. Androstenedione (“Andro”) -1998
Emergence of testosterone precursors.
Ex. Androstenedione (“Andro”) -1998
Dietary supplements Dietary supplements
Testosterone in SportsTestosterone in Sports
Athlete’s desire to improve athletic performance. Athlete’s desire to improve athletic performance.
Floyd Landis- Tour de FranceFloyd Landis- Tour de France Mark McGwire –Major League BaseballMark McGwire –Major League Baseball
Notable Athletes:Notable Athletes:
Supplemental testosterone via injections, pills or topical creams. Supplemental testosterone via injections, pills or topical creams.
Synthesis of AndrostenedioneSynthesis of Androstenedione
CorticosteroneCorticosterone
1. Na+ -OCH3
o
o
2.
O
O
OH
O
H
OH
H H
O
OCH 3
Keto-Enol TautomerizationKeto-Enol Tautomerization
O
H
O
H
O
O
H
OH
H
O
Synthesis of Androstenedione (cont.)Synthesis of Androstenedione (cont.)
AndrostenedioneAndrostenedione
..
........ -
+ +
Proton NMR Spectroscopy
Proton NMR Spectroscopy
AndrostenedioneO
O
H
HHH
H H
(s, 6H)
Testosterone
Electron donating effects of oxygen.
Neighboring protons more shielded.
Electron donating effects of oxygen.
Neighboring protons more shielded.
Proton NMR Spectroscopy
Proton NMR Spectroscopy
(S,1H)
H
(t,1H)
HH
H
HH
H
(s,3H)
(s,3H)
Androstenedione
IR SpectroscopyIR Spectroscopy
O
O
OH
O
Testosterone
IR SpectroscopyIR Spectroscopy
Does Androstenedione Make You Stronger?Does Androstenedione Make You Stronger?
Increases estrone and estradiol levels in men Increases estrone and estradiol levels in men
AndrostenedioneAndrostenedione
O
O
OH
O
OH
HO
AromataseAromatase
TestosteroneTestosterone EstradiolEstradiol
O
HO
Aromatase
Aromatase
EstroneEstrone
The Result?The Result?
Man Boobs! (aka Gynecomastia)Man Boobs! (aka Gynecomastia)
ConclusionsConclusions
Desired results not achieved. Desired results not achieved.
Other methods to bypass laws. Other methods to bypass laws.
Designer Steroids
- BALCO, Olympics
Designer Steroids
- BALCO, Olympics
How to stay ahead of designer steroid manufacturers? How to stay ahead of designer steroid manufacturers?
ReferencesReferences
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. 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.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.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.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.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 the4-hydroxyandrostenedione metabolite. Rapid Commun. Mass Spectrom. 2008; 22: 4147–4157.Cawley et al. The detection of androstenedione abuse in sport: a mass spectrometry strategy to identify the4-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-dihydroxyacetoneSide chain in corticosteroids. Steroids 68 (2003) 139–142.Le Pera et al (2003). A straightforward chemical synthesis of 17-ketosteroids by cleavage of the C-17-dihydroxyacetoneSide chain in corticosteroids. Steroids 68 (2003) 139–142.