19-Nordehydroepiandrosterone

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]

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 classAndrogen; 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
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H25O2
Molar mass273.396 g·mol−1
3D model (JSmol)
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

See also

References
  1. 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". Mol. Cell. Endocrinol. 8 (1): 27–34. doi:10.1016/0303-7207(77)90015-6. PMID 881104. S2CID 24190327.
  2. 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". J Anal Toxicol. 24 (3): 188–93. doi:10.1093/jat/24.3.188. PMID 10774538.
  3. Detlef Thieme; Peter Hemmersbach (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 137–. ISBN 978-3-540-79088-4.
  4. Jehuda Yinon (29 December 2003). Advances in Forensic Applications of Mass Spectrometry. CRC Press. pp. 138–. ISBN 978-0-203-99828-1.



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