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Anabolic-Androgenic Steroids
• Anabolic: stimulate muscle growth• Androgenic: stimulate male sex characteristics
Androstane
CH3
CH3
H
5 -Androstane
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
Male Sex Hormones
Before Castration
AfterCastration
• It was deduced that a secretion of the testes was responsible for male sex characteristics
Testis Extract and Hormones from Urine
Me
Me O
HO
Androsterone
Isolated from UrineLess activity than testis extract
Testis extract: High activity
Me
Me O
O
Androstenedione
More activity but still less than testis extract
Testosterone
Me
MeOH
O
Testosterone
Separation of Androgenicand Anabolic Effects
Me
MeOH
O
Testosterone
Me
MeOH
O
Dihydrotestosterone
5 - reductase
H
MoreActivity
• Receptors for testosterone have the same affinity in the sex accessory organs as in skeletal muscle
Nandrolone
H
MeOH
O
19-Nortestosterone(Nandrolone)
H
MeOH
O
5 -Dihydro-19-nortestosterone(5 -Dihydronandrolone)
5 - reductase
H
Higher activitythan testosterone
Lower activitythan testosterone
Metabolic Deactivationof Testosterone
Me
MeOH
O
HSD
Me
MeOH
OH
HSDMe
MeO
HO
Me
MeO
O
Testosterone Androstenedione
5 - reductase
5 -Dihydrotestosterone Androsterone
reduction at C-3
17α-substituted Derivatives
Me
MeOH
Me
17 -Methyltestosterone
O
17β- Esters
Me
MeO
O
Testosterone Propionate
O
Structure Activity Relationship
Me
MeOH
Me
17 -methylandrost-2-ene-17 -ol
C-3 Oxygennot important
CN
MeOH
O
Me
19 -cyano-17 -methyltestosterone
antagonist
Me
MeOH
OMe
7 -methyltestosterone
- substituenthas no effect
Performance Enhancers
• 17α- alkyl and 17β- esters are not suitable for illegal use by athletes because of their prolonged life and ease of detection
• Prohormones are metabolized into active anabolics and occur naturally in the body
AndrostenedioneDHEA
Me
MeO
HO
Dehydroepiandrosterone
Side Effects
Side Effects of Anabolic-Androgenic Steroids
Both Sexes Men Women
Increased risk of heart attack and stroke
Testicular atrophy
Clitoral enlargement
Increased aggression impotence Beard growth
Liver tumors, jaundice, peliosis hepatitis
Enlarged prostrate
Deepened voice
baldness Breast enlargement
Breast diminution
References
1. Kochakian, C. D. “History of Anabolic-Androgenic Steroids.” Anabolic Steroid Abuse. 1990, 29-50.2. Block, John H. Beale, John M. Organic Medicinal and Pharmaceutical Chemistry. Pa: Lippincott Williams and Wilkins. 2004.3. Kochakian, C. D. “The Effects of Male Hormone on the Protein and Energy Metabolism of Castrate Dogs.” Journal of Nutrition. 1935. 437-59.4. Bowers, A. Edwards, J. “Steroids: Ring A Modified Hormone Analogs, Part 1.” Journal of Medicinal Chemistry. 6. 1962. 5. Celotti, F. Cesi, P. “Anabolic Steroids: A review of their effects on the muscles, of their possible mechanisms of action and of their use in athletics.” Journal of Steroid Biochemistry and Molecular Biology. 43(5). 1992. 469-77.6. Krieg, M. “Characterization of the androgen receptors in the muscle of the rat.” Steroids 28. 1976. 261-74.7. Counsell, R. E. Adelstein, G. W. “!9-Nor- and 19-Substituted 5a-Androst-2-ene Derivatives” Journal of Medicinal Chemistry. 1966. 685-9.8. Delbeke, Frans T. “Prohormones and Sport.” Journal of Steroid Biochemistry and Molecular Biology. 83. 2003. 245-51.
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