Dimethyltrienolone (developmental code name RU-2420) is a synthetic, orally active, and extremely potentanabolic–androgenic steroid (AAS) and 17α-alkylated19-nortestosterone (nandrolone) derivative which was never marketed for medical use.[1] It has among the highest known affinity of any AAS for the androgen (and progesterone) receptors,[2][3] and has been said to be perhaps the most potent AAS to have ever been developed.[1]
Dimethyltrienolone is an extremely potent agonist of the androgen and progesterone receptors and hence AAS and progestogen.[1] In animalbioassays, it was shown to possess more than 100 times the anabolic and androgenicpotency of the reference AAS methyltestosterone.[1] The drug is not a substrate for 5α-reductase and so is not potentiated or inactivated in so-called "androgenic" tissues like the prostate gland or skin.[1] It is also not a substrate for aromatase and so has no estrogenic activity.[1] Due to its lack of estrogenicity, dimethyltrienolone has no propensity for causing estrogenic side effects like gynecomastia.[1] Because of its C17α methyl group and very high resistance to hepaticmetabolism, dimethyltrienolone is said to be exceedingly hepatotoxic.[1]
Relative affinities (%) of dimethyltrienolone and related steroids[4][5]
Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, estradiol for the ER, DEXA for the GR, and aldosterone for the MR.
Chemistry[]
See also: List of androgens/anabolic steroids
Dimethyltrienolone, also known as 7α,17α-dimethyl-δ9,11-19-nortestosterone or as 7α,17α-dimethylestra-4,9,11-trien-17β-ol-3-one, as well as 7α,17α-dimethyltrenbolone, is a syntheticestranesteroid and a 17α-alkylatedderivative of nandrolone (19-nortestosterone).[1] It is the 7α,17α-dimethyl derivative of trenbolone and the 7α-methyl derivative of metribolone,[6] as well as the δ9,11analogue of metribolone and the δ9,11, 17α-methylated derivative of trestolone.[1]
History[]
Dimethyltrienolone was first described in 1967.[1][7] It was never marketed for medical use.[1]
^Waszkowycz B, Clark DE, Frenkel D, Li J, Murray CW, Robson B, Westhead DR (1994). "PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores". J. Med. Chem. 37 (23): 3994–4002. doi:10.1021/jm00049a019. PMID7966160.
^Loughney DA, Schwender CF (1992). "A comparison of progestin and androgen receptor binding using the CoMFA technique". J. Comput.-Aided Mol. Des. 6 (6): 569–81. doi:10.1007/bf00126215. PMID1291626. S2CID22004130.