19-Nordehydroepiandrosterone

{{Short description|Chemical compound}}

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| IUPAC_name = (3S,8R,9S,10R,13S,14S)-3-hydroxy-13-methyl-2,3,4,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one

| image = 19-Nordehydroepiandrosterone.svg

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| routes_of_administration = By mouth

| class = Androgen; anabolic steroid; progestogen

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

| CAS_number = 17916-75-5

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| UNII = 7FA3BH94UY

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| PubChem = 53990402

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| ChemSpiderID = 277545

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| synonyms = {{ubl|19-Nor-DHEA|19-Nor-5-dehydroepiandrosterone|19-Nor-5-DHEA|Estr-5-en-3β-ol-17-one|19-Norandrost-5-en-3β-ol-17-one|3β-Hydroxyestr-5-en-17-one}}

| C=18 | H=25 | O=2

| SMILES = C[C@]12CC[C@@H]3[C@H]4CC[C@@H](CC4=CC[C@H]3[C@@H]1CCC2=O)O

| StdInChI_Ref =

| StdInChI = 1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,12-16,19H,3-10H2,1H3/t12-,13-,14+,15+,16-,18-/m0/s1

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| StdInChIKey = KELRVUIFMYCLHB-MTLKIPAASA-N

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19-Nordehydroepiandrosterone (19-nor-DHEA), or 19-nor-5-dehydroepiandrosterone (19-nor-5-DHEA), is an estrane (19-norandrostane) steroid which was never marketed.{{cite journal | vauthors = Poortman J, Vroegindewey-Jie D, Thijssen JH, Schwarz F | title = Relative binding affinity of androstane and C-19-nor-androstane-steroids for the estradiol-receptor in human myometrial and mammary cancer tissue | journal = Molecular and Cellular Endocrinology | volume = 8 | issue = 1 | pages = 27–34 | date = July 1977 | pmid = 881104 | doi = 10.1016/0303-7207(77)90015-6 | s2cid = 24190327 }} It is the combined derivative of the androgen/anabolic steroid nandrolone (19-nortestosterone) and the androgen prohormone dehydroepiandrosterone (DHEA, or more specifically 5-DHEA). Related compounds include 19-nor-5-androstenediol, bolandiol (19-nor-4-androstenediol), and bolandione (nor-4-androstenedione), which are all known orally active prohormones of nandrolone.{{cite journal | vauthors = Uralets VP, Gillette PA | title =Over-the-counter Δ⁵ anabolic steroids 5-androsen-3,17-dione; 5-androsten-3β, 17β-diol; dehydroepiandrosterone; and 19-nor-5-androsten-3,17-dione: excretion studies in men | journal = Journal of Analytical Toxicology | volume = 24 | issue = 3 | pages = 188–193 | date = April 2000 | pmid = 10774538 | doi = 10.1093/jat/24.3.188 | doi-access = free }}{{cite book| vauthors = Thieme D, Hemmersbach P |title=Doping in Sports|url=https://books.google.com/books?id=R-hIC-caIn8C&pg=PA137|date=18 December 2009|publisher=Springer Science & Business Media|isbn=978-3-540-79088-4|pages=137–}}{{cite book| vauthors = Villain M, Cirimele V, Kintz P | chapter = Substance Abuse in Sports: Detection of Doping Agents in Hair by Mass Spectrometry | veditors = Yinon J |title=Advances in Forensic Applications of Mass Spectrometry | chapter-url = https://books.google.com/books?id=T0vGENZVDaoC&pg=PA138 |date=29 December 2003|publisher=CRC Press|isbn=978-0-203-99828-1|pages=138–}} 19-Nor-DHEA may occur as a metabolite of bolandione and related steroids.