1-Androstenedione

1-Androstenedione

Clinical data
Routes of administration	Oral
Identifiers
IUPAC name (5S,8R,9S,10R,13S,14S)-10,13-dimethyl-5,6,7,8,9,11,12,14,15,16-decahydro-4H-cyclopenta[a]phenanthrene-3,17-dione
Synonyms	5α-Androst-1-ene-3,17-dione
CAS Number	571-40-4
PubChem (CID)	11196935
ChemSpider	9372004
UNII	C1091EX356
Chemical and physical data
Formula	C19H26O2
Molar mass	286.415 g/mol
3D model (Jmol)	Interactive image
SMILES O=C4\C=C/[C@]2([C@@H](CC[C@H]3[C@@H]1CCC(=O)[C@@]1(C)CC[C@H]23)C4)C
InChI InChI=1S/C19H26O2/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/h7,9,12,14-16H,3-6,8,10-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1 Key:WJIQCDPCDVWDDE-WZNAKSSCSA-N

1-Androstenedione, or 5α-androst-1-ene-3,17-dione, also known as 4,5α-dihydro-δ¹-4-androstenedione, is a synthetic androgen and anabolic steroid. It is a 5α-reduced isomer of the endogenous steroid Δ⁴-androstenedione and acts as an androgen prohormone of 1-testosterone (4,5α-dihydro-δ¹-testosterone), a derivative of dihydrotestosterone (DHT).^[1]

1-Androstenedione is on the World Anti-Doping Agency's list of prohibited substances,^[2] and is therefore banned from use in most major sports.

See also

• 1-Androstenediol

References

1. Zhang H, Qiu Z (December 2006). "An efficient synthesis of 5α-androst-1-ene-3,17-dione". Steroids. 71 (13-14): 1088–90. doi:10.1016/j.steroids.2006.09.008. PMID 17123559.
2. "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2012-07-17.