Bolandiol

Bolandiol

Identifiers
IUPAC name (3S,8R,9S,10R,13S,14S,17S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
Synonyms	19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; Estr-4-ene-3β,17β-diol; 3β-Dihydronandrolone
CAS Number	19793-20-5
PubChem (CID)	9835303
ChemSpider	8011024
ChEMBL	CHEMBL2106664
Chemical and physical data
Formula	C18H28O2
Molar mass	276.42 g·mol^−1
3D model (Jmol)	Interactive image
SMILES 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
InChI InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1 Key:CMXKUJNZWYTFJN-XFUVECHXSA-N

Bolandiol (INN), also known as 19-nor-4-androstenediol, estr-4-en-3β,17β-diol, or 3β-dihydronandrolone, is an anabolic-androgenic steroid (AAS) that was never marketed.^[1] A dipropionate ester, bolandiol dipropionate (brand names Anabiol, Storinal; former developmental code name SC-7525), has been marketed.^[1][2] Bolandiol (and its dipropionate ester) is unique among AAS in that it reportedly also possesses estrogenic and progestogenic activity.^[3][4]

Bolandiol is on the World Anti-Doping Agency's list of prohibited substances,^[5] and is therefore banned from use in most major sports. It is a potential metabolic precursor to nandrolone.^[6] However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.^[7][8]

See also

• 4-Androstenediol
• 19-Nor-5-androstenediol
• 19-Nor-5-androstenedione
• Bolandione (19-nor-4-androstenedione)
• Bolenol (17α-ethyl-19-nor-5-androstenol)

References

1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 899–. ISBN 978-1-4757-2085-3.
2. Thomas E. Hyde; Marianne S. Gengenbach (2007). Conservative Management of Sports Injuries. Jones & Bartlett Learning. pp. 1100–. ISBN 978-0-7637-3252-3.
3. Hormones: Advances in Research and Application: 2011 Edition. ScholarlyEditions. 9 January 2012. pp. 59–. ISBN 978-1-4649-2242-8.
4. 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.
5. "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2012-07-17.
6. 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. 766 (2): 257–263. doi:10.1016/S0378-4347(01)00506-0.
7. 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. doi:10.1007/s004210100395. PMID 11417430.
8. Van Gammeren, D; Falk, D; Antonio, J (2002). "Effects of norandrostenedione and norandrostenediol in resistance-trained men". Nutrition. 18 (9): 734–7. doi:10.1016/s0899-9007(02)00834-1. PMID 12297208.