19-Nordehydroepiandrosterone

19-Nordehydroepiandrosterone
Clinical data
Other names	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;
Routes of; administration	By mouth
Drug class	Androgen; anabolic steroid; progestogen
Identifiers
	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;
CAS Number	17916-75-5 ;
PubChem CID	53990402;
ChemSpider	277545;
UNII	7FA3BH94UY;
Chemical and physical data
Formula	C18H25O2
Molar mass	273.396 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@@H]3[C@H]4CC[C@@H](CC4=CC[C@H]3[C@@H]1CCC2=O)O;
	InChI InChI=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; Key:KELRVUIFMYCLHB-MTLKIPAASA-N;

19-Nordehydroepiandrosterone (19-nor-DHEA), or 19-nor-5-dehydroepiandrosterone (19-nor-5-DHEA), is an estrane (19-norandrostane) steroid which was never marketed.^[1]^[2] It is the combined derivative of the androgen/anabolic steroid nandrolone (19-nortestosterone) and the androgen prohormone dehydroepiandrosterone (DHEA, or more specifically 5-DHEA).^[1]^[2] 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.^[2]^[3]^[4] 19-Nor-DHEA may occur as a metabolite of bolandione and related steroids.^[2]

References

^ ^a ^b Poortman J, Vroegindewey-Jie D, Thijssen JH, Schwarz F (July 1977). "Relative binding affinity of androstane and C-19-nor-androstane-steroids for the estradiol-receptor in human myometrial and mammary cancer tissue". Molecular and Cellular Endocrinology. 8 (1): 27–34. doi:10.1016/0303-7207(77)90015-6. PMID 881104. S2CID 24190327.
^ ^a ^b ^c ^d Uralets VP, Gillette PA (April 2000). "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 of Analytical Toxicology. 24 (3): 188–193. doi:10.1093/jat/24.3.188. PMID 10774538.
^ Thieme D, Hemmersbach P (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 137–. ISBN 978-3-540-79088-4.
^ Villain M, Cirimele V, Kintz P (29 December 2003). "Substance Abuse in Sports: Detection of Doping Agents in Hair by Mass Spectrometry". In Yinon J (ed.). Advances in Forensic Applications of Mass Spectrometry. CRC Press. pp. 138–. ISBN 978-0-203-99828-1.

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Clinical data

Other names	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
Routes of administration	By mouth
Drug class	Androgen; anabolic steroid; progestogen
Identifiers
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
CAS Number	17916-75-5^Y
PubChem CID	53990402
ChemSpider	277545
UNII	7FA3BH94UY
Chemical and physical data
Formula	C₁₈H₂₅O₂
Molar mass	273.396 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@@H]3[C@H]4CC[C@@H](CC4=CC[C@H]3[C@@H]1CCC2=O)O
InChI InChI=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 Key:KELRVUIFMYCLHB-MTLKIPAASA-N