5α-Androst-2-ene-17-one - Misplaced Pages

(Redirected from 5α-Androst-2-en-17-one) Chemical compound Not to be confused with Androstenone. Pharmaceutical compound

5α-Androst-2-ene-17-one
Clinical data

Other names	5α-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
IUPAC name (5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopentaphenanthren-17-one
CAS Number	963-75-7
PubChem CID	239425
ChemSpider	92089
UNII	AHC8P4E4ZL
CompTox Dashboard (EPA)	DTXSID30914585
ECHA InfoCard	100.012.289
Chemical and physical data
Formula	C₁₉H₂₈O
Molar mass	272.432 g·mol
3D model (JSmol)	Interactive image
SMILES C34CC2(CCC1C\C=C/C12C)4CCC3=O
InChI 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 Key:ISJVDMWNISUFRJ-HKQXQEGQSA-N

5α-Androst-2-en-17-one, known by the nickname Delta-2, 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 and is also a pheromone found in elephants and boars. 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

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.
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.
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

17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
5α-Dihydronormethandrone

5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
5α-Dihydronorethisterone

SARMsTooltip Selective androgen receptor modulator

Antagonists

Agonists	Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

This article about a steroid is a stub. You can help Misplaced Pages by expanding it.

This drug article relating to the genito-urinary system is a stub. You can help Misplaced Pages by expanding it.