Bolandiol

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-tetradecahydrocyclopenta[a]phenanthrene-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−1
3D model (JSmol)	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-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed.^[1] However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed.^[1]^[2] Bolandiol and its dipropionate ester are unique among AASs in that they 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]

References

^ ^a ^b 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.
^ Hyde TE, Gengenbach MS (2007). Conservative Management of Sports Injuries. Jones & Bartlett Learning. pp. 1100–. ISBN 978-0-7637-3252-3.
^ Action QA, ed. (9 January 2012). Hormones: Advances in Research and Application (2011 ed.). ScholarlyEditions. pp. 59–. ISBN 978-1-4649-2242-8.
^ 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.
^ "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.
^ 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.
^ 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.
^ 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.

[Elks2014-1] 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.

[HydeGengenbach2007-2] 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.

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See also

References