Chemistry:Dienolone

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Dienolone (developmental code name RU-3118; online product names Trenazone,[1] Dienazone), or nordienolone, also known as 19-nor-δ9(10)-testosterone, δ9(10)-nandrolone, or estra-4,9(10)-dien-17β-ol-3-one, is a synthetic anabolic-androgenic steroid (AAS) of the 19-nortestosterone group that was never marketed.[2] It has been found to possess slightly lower affinity for the androgen receptor (AR) and progesterone receptor (PR) relative to nandrolone in rat and rabbit tissue bioassays, whereas trenbolone was found to possess the same affinity for the AR as dienolone but several-fold increased affinity for the PR.[3] Dienedione (the 17-keto analogue of dienolone, also known as 19-nor-4,9-androstadienedione) is thought to be a prohormone of dienolone,[4] while methyldienolone and ethyldienolone are orally active 17α-alkylated AAS derivatives of dienolone.[5][6] In contrast, dienogest, the 17α-cyanomethyl derivative of dienolone, is a potent progestogen and antiandrogen.[7]

Chemistry

Synthesis

Polyvinylpyridine

Prenortestosterone [1089-78-7][8] (see under nandrolone synthesis) can be brominated. 2x dehydrohalogenation step then leads to dienolone.[9][10] In the old method a mixture of molecular bromine and pyridine had been used as the reagents. However, in the new and improved synthesis the reagent was changed to poly(vinylpyridine) bromide perbromide (P(4-VPBPB)) [91650-35-0],[11] polyvinyl(pyridine) (PVP or P4VP) [25232-41-1] and pyridine. This gives an improved yield of product

Application

Whilst Dienedione can be used as a precursor to trenbolone, it is also fully possible to employ Dienolone (Dehydronandrolone), as was recently claimed.[12][13][14]

The synthesis of 11β-methyl-19-nortestosterone is an additional use of dienolone.

See also

References

  1. ↑ "A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates". Steroids 92: 74–80. December 2014. doi:10.1016/j.steroids.2014.09.006. PMID 25286236. 
  2. ↑ "STATUS DECISION OF CONTROLLED AND NON-CONTROLLED SUBSTANCE(S)". August 12, 2011. https://isomerdesign.com/Cdsa/HC/StatusDecisions/A-2013-00235%20-%20PDFs/C-Dienolone-2011-08-12.pdf. 
  3. ↑ "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry 27 (1–3): 255–269. 1987. doi:10.1016/0022-4731(87)90317-7. PMID 3695484. 
  4. ↑ "2009 - Final Rule: Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act". https://www.deadiversion.usdoj.gov/fed_regs/rules/2009/fr1204.htm. 
  5. ↑ "Synthetic Anabolic Agents: Steroids and Nonsteroidal Selective Androgen Receptor Modulators". Doping in Sports. Springer Science & Business Media. 18 December 2009. pp. 103, 157, 162–164. ISBN 978-3-540-79088-4. https://books.google.com/books?id=R-hIC-caIn8C&pg=PA103. 
  6. ↑ "Dissociation of the androgenic and other hormonal activities from the protein anabolic effects of steroids". Anabolic-Androgenic Steroids. Springer Science & Business Media. 6 December 2012. pp. 380–381. doi:10.1007/978-3-642-66353-6_11. ISBN 978-3-642-66353-6. https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA380. 
  7. ↑ "Dienogest". Drugs 56 (5): 825–33; discussion 834–5. November 1998. doi:10.2165/00003495-199856050-00007. PMID 9829156. 
  8. ↑ Patrick J. Bednarski, et al. U.S. Patent 4,745,109 (1988 to Washington Research Foundation).
  9. ↑ Menzenbach, B.; Hübner, M. (October 1986). "Synthese von 3‐Keto‐4,9‐diensteroiden mit polymeren Reagenzien". Zeitschrift für Chemie 26 (10): 371–371. doi:10.1002/zfch.19860261007. https://onlinelibrary.wiley.com/doi/10.1002/zfch.19860261007. 
  10. ↑ Muddana, S. S.; Price, A. M.; MacBride, M. M.; Peterson, B. R. (1 October 2004). "11β-Alkyl-Δ 9 -19-Nortestosterone Derivatives: High-Affinity Ligands and Potent Partial Agonists of the Androgen Receptor". Journal of Medicinal Chemistry 47 (21): 4985–4988. doi:10.1021/jm0342515. https://pubs.acs.org/doi/10.1021/jm0342515. 
  11. ↑ "Poly(4-vinylpyridinium bromide perbromide)". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. 2001. doi:10.1002/047084289X.rp188. https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rp188. 
  12. ↑ Anna Rencurosi, WO2022106574 (to Fabbrica Italiana Sintetici SpA (FIS)).
  13. ↑ Anna Rencurosi & Roberto Brescello, WO2022106566 (to Fabbrica Italiana Sintetici SpA (FIS)).
  14. ↑ 张峥斌, et al. CN117659109 (2024 to Inner Mongolia Junye Biological Pharmaceutical Co ltd, Jiangxi Junye Biological Pharmaceutical Co ltd, Zhejiang Xianju Junye Pharmaceutical Co ltd).



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