5α-Androst-2-ene-17-one

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Not to be confused with Androstenone.
5α-Androst-2-ene-17-one
Clinical data
Other names5α-Androst-2-en-17-one; 17-Oxo-5α-androst-2-ene; Delta-2-androst-17-one; (+)-Androst-2-en-17-one; Occlesterone
Routes of
administration		Oral
Identifiers
  • (5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.012.289 Edit this at Wikidata
Chemical and physical data
FormulaC19H28O
Molar mass272.432 g/mol g·mol−1
3D model (JSmol)
  • C[C@@]34CC[C@H]2[C@@H](CCC1C\C=C/C[C@@]12C)[C@@H]4CCC3=O
  • InChI=InChI==1S/C19H28O/c1-18-11-4-3-5-13(18)6-7-14-15-8-9-17(20)19(15,2)12-10-16(14)18/h3-4,13-16H,5-12H2,1-2H3/t13-,14+,15+,16+,18+,19+/m1/s1 checkY
  • Key:ISJVDMWNISUFRJ-HKQXQEGQSA-N checkY

5α-Androst-2-en-17-one is an endogenous, naturally occurring, orally active anabolic-androgenic steroid (AAS) and a derivative of dihydrotestosterone (DHT). It is a metabolite of dehydroepiandrosterone (DHEA) in the body[1][2] and is also a pheromone found in elephants and boars.[3] 5α-Androst-2-en-17-one has been sold on the Internet as a "dietary supplement". It resembles desoxymethyltestosterone (17α-methyl-5α-androst-2-en-17β-ol) in chemical structure and may act as an androgen prohormone.

References

  1. ^ Callies, F; Arlt, W; Siekmann, L; Hübler, D; Bidlingmaier, F; Allolio, B (2000). "Influence of oral dehydroepiandrosterone (DHEA) on urinary steroid metabolites in males and females". Steroids. 65 (2): 98–102. doi:10.1016/S0039-128X(99)00090-2. PMID 10639021.
  2. ^ Gower, DB; Mallet, AI; Watkins, WJ; Wallace, LM (1997). "Transformations of steroid sulphates by human axillary bacteria. A mechanism for human odour formation?". Biochemical Society Transactions. 25 (1): 16S. doi:10.1042/bst025016s. PMID 9056914.
  3. ^ Marchlewska-Koj, A.; Lepri, J. J. (2001). "Chemical signals in vertebrates 9". Springer. 9: 131. ISBN 978-0-306-46682-3.



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