Bolandiol

Bolandiol
Names
	Systematic IUPAC 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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2106664;
ChemSpider	8011024;
PubChem CID	9835303;
CompTox Dashboard (EPA)	DTXSID9041027 ;
	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; InChI=1/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-XFUVECHXBJ;
	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;
Properties
Chemical formula	C18H28O2
Molar mass	276.420 g·mol−1
	Except where otherwise noted, 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" (PDF). 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.
^ 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.

[1] 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.

[2] "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2012-07-17.

[3] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[4] 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.

[5] 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.

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