19-Nordehydroepiandrosterone

Chemical compound From Wikipedia, the free encyclopedia

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]

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
Quick facts Clinical data, Other names ...
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
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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

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