Dienolone

Dienolone
Clinical data
Other names	RU-3118; Nordienolone, Dehydronandrolone.
ATC code	None;
Identifiers
	IUPAC name (8S,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one;
CAS Number	6218-29-7;
PubChem CID	11747706;
ChemSpider	9922410;
UNII	ZX4VV1AKUF;
ChEMBL	ChEMBL2311179;
CompTox Dashboard (EPA)	DTXSID80471835 ;
ECHA InfoCard	100.125.823
Chemical and physical data
Formula	C18H24O2
Molar mass	272.388 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2O;
	InChI InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,15-17,20H,2-9H2,1H3/t15-,16+,17+,18+/m1/s1; Key:PUQSDJZESAQGQS-OWSLCNJRSA-N;

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

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.

References

^ Waller CC, McLeod MD (December 2014). "A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates". Steroids. 92: 74–80. doi:10.1016/j.steroids.2014.09.006. hdl:1885/15429. PMID 25286236. S2CID 11504510.
^ "STATUS DECISION OF CONTROLLED AND NON-CONTROLLED SUBSTANCE(S)" (PDF). August 12, 2011. Retrieved April 29, 2025.
^ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry. 27 (1–3): 255–269. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.
^ "2009 - Final Rule: Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act". Archived from the original on January 8, 2010.
^ Thevis M, Schanzer W (18 December 2009). "Synthetic Anabolic Agents: Steroids and Nonsteroidal Selective Androgen Receptor Modulators". In Thieme D, Hemmersbach P (eds.). Doping in Sports. Springer Science & Business Media. pp. 103, 157, 162–164. ISBN 978-3-540-79088-4.
^ Potts GO, Arnold A, Beyler AL (6 December 2012). "Dissociation of the androgenic and other hormonal activities from the protein anabolic effects of steroids". In Kochakian CD (ed.). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 380–381. doi:10.1007/978-3-642-66353-6_11. ISBN 978-3-642-66353-6.
^ Foster RH, Wilde MI (November 1998). "Dienogest". Drugs. 56 (5): 825–33, discussion 834–5. doi:10.2165/00003495-199856050-00007. PMID 9829156. S2CID 262326901.
^ Patrick J. Bednarski, et al. U.S. patent 4,745,109 (1988 to Washington Research Foundation).
^ 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.
^ 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.
^ Wood WF (2001). "Poly(4-vinylpyridinium bromide perbromide)". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rp188.
^ Anna Rencurosi, WO2022106574 (to Fabbrica Italiana Sintetici SpA (FIS)).
^ Anna Rencurosi & Roberto Brescello, WO2022106566 (to Fabbrica Italiana Sintetici SpA (FIS)).
^ 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).

[pmid25286236-1] Waller CC, McLeod MD (December 2014). "A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates". Steroids. 92: 74–80. doi:10.1016/j.steroids.2014.09.006. hdl:1885/15429. PMID 25286236. S2CID 11504510.

[HealthCanada2011-2] "STATUS DECISION OF CONTROLLED AND NON-CONTROLLED SUBSTANCE(S)" (PDF). August 12, 2011. Retrieved April 29, 2025.

[pmid3695484-3] Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry. 27 (1–3): 255–269. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.

[USDOJ2009-4] "2009 - Final Rule: Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act". Archived from the original on January 8, 2010.

[ThiemeHemmersbach2009-5] Thevis M, Schanzer W (18 December 2009). "Synthetic Anabolic Agents: Steroids and Nonsteroidal Selective Androgen Receptor Modulators". In Thieme D, Hemmersbach P (eds.). Doping in Sports. Springer Science & Business Media. pp. 103, 157, 162–164. ISBN 978-3-540-79088-4.

[Kochakian2012-6] Potts GO, Arnold A, Beyler AL (6 December 2012). "Dissociation of the androgenic and other hormonal activities from the protein anabolic effects of steroids". In Kochakian CD (ed.). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 380–381. doi:10.1007/978-3-642-66353-6_11. ISBN 978-3-642-66353-6.

[pmid9829156-7] Foster RH, Wilde MI (November 1998). "Dienogest". Drugs. 56 (5): 825–33, discussion 834–5. doi:10.2165/00003495-199856050-00007. PMID 9829156. S2CID 262326901.

[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.

[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.

[11] Wood WF (2001). "Poly(4-vinylpyridinium bromide perbromide)". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. 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).

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

Chemistry

Synthesis

Application

See also

References