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Bolandiol

Clinical data
Other names	19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; Estr-4-ene-3β,17β-diol; 3β-Dihydronandrolone
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-tetradecahydrocyclopentaphenanthrene-3,17-diol
CAS Number	19793-20-5
PubChem CID	9835303
ChemSpider	8011024
UNII	49SD6G16U5
ChEBI	CHEBI:145661
ChEMBL	ChEMBL2106664
CompTox Dashboard (EPA)	DTXSID9041027
Chemical and physical data
Formula	C18H28O2
Molar mass	276.420 g·mol
3D model (JSmol)	Interactive image
SMILES O4/C=C2\(1CC3((O)CC31CC2)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-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed. However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed. Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity.

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

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. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 899–. ISBN 978-1-4757-2085-3.
2. Hyde TE, Gengenbach MS (2007). Conservative Management of Sports Injuries. Jones & Bartlett Learning. pp. 1100–. ISBN 978-0-7637-3252-3.
3. Action QA, ed. (9 January 2012). Hormones: Advances in Research and Application (2011 ed.). ScholarlyEditions. pp. 59–. ISBN 978-1-4649-2242-8.
4. Attardi BJ, Page ST, Hild SA, Coss CC, Matsumoto AM (February 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. Archived from the original (PDF) on 2012-05-13. Retrieved 2012-07-17.
6. Dehennin L, Bonnaire Y, Plou P (January 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. PMID 11824814.
7. Van Gammeren D, Falk D, Antonio J (May 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): 426–431. doi:10.1007/s004210100395. PMID 11417430. S2CID 13129479.
8. van Gammeren D, Falk D, Antonio J (September 2002). "Effects of norandrostenedione and norandrostenediol in resistance-trained men". Nutrition. 18 (9): 734–737. doi:10.1016/s0899-9007(02)00834-1. PMID 12297208.

• Anabolic–androgenic steroids
• Estranes
• Estrogens
• Prodrugs
• Progestogens
• Cyclohexenols
• Cyclopentanols
• Abandoned drugs