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 classAndrogen; anabolic steroid; progestogen
Identifiers
  • (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)
  • C[C@]12CC[C@@H]3[C@H]4CC[C@@H](CC4=CC[C@H]3[C@@H]1CCC2=O)O
  • 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]

Synthesis

The chemical synthesis of 19-Nordehydroepiandrosterone was reported.[5]

The enone group in Bolandione (1) is protected with isopropenyl acetate to give the corresponding enol acetate (3-Hydroxy-17-oxoestra-3,5-dien-3-yl acetate) PC11278466 (2). Ketalization of the remaining carbonyl with ethyleneglycol in the presence of triethyl orthoformate gives (3). Reduction of the enol ether by treatment with sodium borohydride occurred to give PC118447212 (4). Hydrolytic removal of the cyclic ketal in weak acid completed the synthesis of 19-Nor-DHEA (5).

See also

References

  1. ^ 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.
  2. ^ 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.
  3. ^ Thieme D, Hemmersbach P (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 137–. ISBN 978-3-540-79088-4.
  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.
  5. ^ Tang Sihua, et al. CN117820407 (2024 to Hubei Tongtong Steroidal Drug Research Institute Co ltd).
allikas: https://en.wikipedia.org/wiki/19-Nordehydroepiandrosterone