:5α-Androst-2-ene-17-one

{{Short description|Chemical compound}}

{{Distinguish|Androstenone}}

{{Drugbox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| IUPAC_name = (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

| image = 5alpha-androst-2-ene-17-one.svg

| width =

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 963-75-7

| CAS_supplemental =

| ATC_prefix =

| ATC_suffix =

| ATC_supplemental =

| PubChem = 239425

| IUPHAR_ligand =

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 92089

| UNII_Ref={{fdacite|correct|FDA}}

| UNII = AHC8P4E4ZL

| KEGG =

| ChEBI =

| ChEMBL =

| C=19 | H=28 | O=1

| SMILES = C[C@@]34CC[C@H]2[C@@H](CCC1C\C=C/C[C@@]12C)[C@@H]4CCC3=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ISJVDMWNISUFRJ-HKQXQEGQSA-N

| synonyms = 5α-Androst-2-en-17-one; 17-Oxo-5α-androst-2-ene; Delta-2-androst-17-one; (+)-Androst-2-en-17-one; Occlesterone

}}

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{{cite journal | vauthors = Callies F, Arlt W, Siekmann L, Hübler D, Bidlingmaier F, Allolio B | s2cid = 2630118 | title = Influence of oral dehydroepiandrosterone (DHEA) on urinary steroid metabolites in males and females | journal = Steroids | volume = 65 | issue = 2 | pages = 98–102 | date = February 2000 | pmid = 10639021 | doi = 10.1016/S0039-128X(99)00090-2 }}{{cite journal | vauthors = Gower DB, Mallet AI, Watkins WJ, Wallace LM | title = Transformations of steroid sulphates by human axillary bacteria. A mechanism for human odour formation? | journal = Biochemical Society Transactions | volume = 25 | issue = 1 | pages = 16S | date = February 1997 | pmid = 9056914 | doi = 10.1042/bst025016s }} and is also a pheromone found in elephants and boars.{{Cite book | vauthors = Marchlewska-Koj A, Lepri JJ, Müller-Schwarze D |year=2001 |title=Chemical signals in vertebrates 9 |publisher=Springer |volume=9 |pages=131 |isbn=978-0-306-46682-3 }} 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.