19-Nordehydroepiandrosterone

Last updated
19-Nordehydroepiandrosterone
19-Nordehydroepiandrosterone.svg
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
  • (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
Formula C18H25O2
Molar mass 273.396 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]

Contents

Synthesis

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

19-Nordehydroepiandrosterone synthesis.svg

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. 1 2 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. 1 2 3 4 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).
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