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5α-Androst-2-ene-17-one

From Wikipedia, the free encyclopedia
(Redirected from5α-Androst-2-en-17-one)
Chemical compound
Not to be confused withAndrostenone.
Pharmaceutical compound
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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.012.289Edit this at Wikidata
Chemical and physical data
FormulaC19H28O
Molar mass272.432 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, known by the nicknameDelta-2, is anendogenous,naturally occurring,orally activeanabolic-androgenic steroid (AAS) and aderivative ofdihydrotestosterone (DHT). It is ametabolite ofdehydroepiandrosterone (DHEA) in the body[1][2] and is also apheromone found inelephants andboars.[3] 5α-Androst-2-en-17-one has been sold on theInternet as a "dietary supplement". It resemblesdesoxymethyltestosterone (17α-methyl-5α-androst-2-en-17β-ol) inchemical structure and may act as anandrogen prohormone.

References

[edit]
  1. ^Callies F, Arlt W, Siekmann L, Hübler D, Bidlingmaier F, Allolio B (February 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.S2CID 2630118.
  2. ^Gower DB, Mallet AI, Watkins WJ, Wallace LM (February 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 JJ, Müller-Schwarze D (2001).Chemical signals in vertebrates 9. Vol. 9. Springer. p. 131.ISBN 978-0-306-46682-3.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists


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