5α-Dihydronormethandrone

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5α-Dihydronormethandrone
5α-Dihydronormethandrone.svg
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

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]

Relative affinities (%) of normethandrone and metabolites
Compound PR AR ER GR MR SHBG CBG
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 PR, testosterone for the AR, estradiol for the ER, dexamethasone for the GR, and aldosterone for the MR. Sources: See template.

See also[edit]

References[edit]

  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