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5α-Dihydronormethandrone

5α-Dihydronormethandrone (5α-DHNMT; developmental code name RU-575), also known as 17α-methyl-4,5α-dihydro-19-nortestosterone or as 17α-methyl-5α-estran-17β-ol-3-one, is an androgen/anabolic steroid and a likely metabolite of normethandrone formed by 5α-reductase.[1][2] Analogously to nandrolone and its 5α-reduced metabolite 5α-dihydronandrolone, 5α-DHNMT shows reduced affinity for the androgen receptor relative to normethandrone.[1] Its affinity for the androgen receptor is specifically about 33 to 60% of that of normethandrone.[1]

5α-Dihydronormethandrone
Clinical data
Other names5α-DHNMT; RU-575; 17α-Methyl-4,5α-dihydro-19-nortestosterone; 17α-Methyl-5α-estran-17β-ol-3-one
Identifiers
  • (5S,8R,9R,10S,13S,14S,17S)-17-Hydroxy-13,17-dimethyl-1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC19H30O2
Molar mass290.447 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@H]3CCC(=O)C4
  • InChI=MDXRCPMWSFWIEZ-MOVWYJJTSA-N
  • Key:1S/C19H30O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15+,16+,17-,18-,19-/m0/s1
Relative affinities (%) of normethandrone and metabolites
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin CBGTooltip Corticosteroid binding globulin
Normethandrone 75–125 125–150 <1 1–5 <1 ? ?
5α-Dihydronormethandrone 15–25 50–75 ? <1 ? ? ?
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, estradiol for the ERTooltip estrogen receptor, dexamethasone for the GRTooltip glucocorticoid receptor, and aldosterone for the MRTooltip mineralocorticoid receptor. Sources: See template.

See also

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References

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  1. ^ a b c Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". J. Steroid Biochem. 27 (1–3): 255–69. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.
  2. ^ Schjølberg, T. H. (2013). In Vitro Synthesis of Metabolites of three Anabolic Androgenic Steroids, by Human Liver Microsomes (Master's thesis, Institutt for bioteknologi). https://brage.bibsys.no/xmlui/handle/11250/246018


 

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