1-Androstenediol

1-Androstenediol
Clinical data
ATC code	None;
Identifiers
	IUPAC name (3R,5S,8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17-diol;
CAS Number	5323-27-3;
PubChem CID	11300765;
ChemSpider	9475742;
UNII	V7W74907I7;
CompTox Dashboard (EPA)	DTXSID60627737 ;
Chemical and physical data
Formula	C19H30O2
Molar mass	290.447 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC[C@@H]4[C@@]3(C=C[C@@H](C4)O)C;
	InChI InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,12-17,20-21H,3-6,8,10-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1; Key:RZFGPAMUAXASRE-YSZCXEEOSA-N;

1-Androstenediol, or 5α-androst-1-ene-3β,17β-diol, also known as 4,5α-dihydro-δ¹-4-androstenediol, is a prohormone of 1-testosterone (Δ¹-DHT).^[1]^[2] It has been used as a dietary supplement, and is identified by the World Anti-Doping Agency as a prohibited substance related to anabolic steroids.^[3]

References

^ Schnäuzer W, Thevis M (26 July 2012). "Detecting Illegal Use of Androgens and SARMs". In Nieschlag E, Behre HM, Nieschlag S (eds.). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 521–. ISBN 978-1-107-01290-5.
^ Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 300–. ISBN 978-0-9828280-1-4.
^ Parr MK, Opfermann G, Geyer H, Westphal F, Sönnichsen FD, Zapp J, et al. (May 2011). "Seized designer supplement named "1-Androsterone": identification as 3β-hydroxy-5α-androst-1-en-17-one and its urinary elimination". Steroids. 76 (6): 540–547. doi:10.1016/j.steroids.2011.02.001. PMID 21310167.

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Clinical data

ATC code	None
Identifiers
IUPAC name (3R,5S,8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17-diol
CAS Number	5323-27-3
PubChem CID	11300765
ChemSpider	9475742
UNII	V7W74907I7
CompTox Dashboard (EPA)	DTXSID60627737
Chemical and physical data
Formula	C₁₉H₃₀O₂
Molar mass	290.447 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC[C@@H]4[C@@]3(C=C[C@@H](C4)O)C
InChI InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,12-17,20-21H,3-6,8,10-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1 Key:RZFGPAMUAXASRE-YSZCXEEOSA-N