Bolandiol
| Bolandiol | |
|---|---|
 | |
| Systematic name (3β,17β)-Estr-4-ene-3,17-diol | |
| Other names 19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; (3β,17β)-Dihydroxyestr-4-ene; Estr-4-ene-3β,17β-diol | |
| Identifiers | |
| CAS number | 19793-20-5  |
| PubChem | 9835303 |
| ChemSpider | 8011024 |
| Jmol-3D images | {{#if:O[C@@H]4/C=C2\[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4|Image 1 |
| |
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| Properties | |
| Molecular formula | C18H28O2 |
| Molar mass | 276.41 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Bolandiol (19-norandrostenediol) is a synthetic anabolic steroid. It is hypothesized by interaction with androgen receptors, estrogen receptors, and progestin receptors.[1]
Bolandiol is on the World Anti-Doping Agency's list of prohibited substances,[2] and is therefore banned from use in most major sports. It is a potential metabolic precursor to nandrolone.[3] However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.[4][5]
References
- ↑ Attardi, BJ; Page, ST; Hild, SA; Coss, CC; Matsumoto, AM (2010). "Mechanism of action of bolandiol (19-nortestosterone-3beta,17beta-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities". The Journal of steroid biochemistry and molecular biology 118 (3): 151–61. doi:10.1016/j.jsbmb.2009.11.008. PMC 2831543. PMID 19941958.
- ↑ "The World Anti-Doping Code: The 2012 Prohibited List". World Anti-Doping Agency. Retrieved 2012-07-17.
- ↑ Dehennin, L.; Bonnaire, Y.; Plou, Ph. (2002). "Human nutritional supplements in the horse: comparative effects of 19-norandrostenedione and 19-norandrostenediol on the 19-norsteroid profile and consequences for doping control". Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences 766 (2): 257–263. doi:10.1016/S0378-4347(01)00506-0.
- ↑ Van Gammeren, D; Falk, D; Antonio, J (2001). "The effects of supplementation with 19-nor-4-androstene-3,17-dione and 19-nor-4-androstene-3,17-diol on body composition and athletic performance in previously weight-trained male athletes". European journal of applied physiology 84 (5): 426–31. PMID 11417430.
- ↑ Van Gammeren, D; Falk, D; Antonio, J (2002). "Effects of norandrostenedione and norandrostenediol in resistance-trained men". Nutrition 18 (9): 734–7. PMID 12297208.