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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
  • 6424-04-0 Y
PubChem CID
  • 22792507
UNII
  • JHH2FT7BLU
Chemical and physical data
FormulaC19H30O2
Molar mass290.447 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 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


dihydronormethandrone, dhnmt, developmental, code, name, also, known, 17α, methyl, dihydro, nortestosterone, 17α, methyl, estran, 17β, androgen, anabolic, steroid, likely, metabolite, normethandrone, formed, reductase, analogously, nandrolone, reduced, metabol. 5a Dihydronormethandrone 5a DHNMT developmental code name RU 575 also known as 17a methyl 4 5a dihydro 19 nortestosterone or as 17a methyl 5a estran 17b ol 3 one is an androgen anabolic steroid and a likely metabolite of normethandrone formed by 5a reductase 1 2 Analogously to nandrolone and its 5a reduced metabolite 5a dihydronandrolone 5a 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 5a DihydronormethandroneClinical dataOther names5a DHNMT RU 575 17a Methyl 4 5a dihydro 19 nortestosterone 17a Methyl 5a estran 17b ol 3 oneIdentifiersIUPAC name 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 oneCAS Number6424 04 0 YPubChem CID22792507UNIIJHH2FT7BLUChemical and physical dataFormulaC 19H 30O 2Molar mass290 447 g mol 13D model JSmol Interactive imageSMILES C C 12CC C H 3 C H C H 1CC C 2 C O CC C H 4 C H 3CCC O C4InChI InChI MDXRCPMWSFWIEZ MOVWYJJTSA NKey 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 vte 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 globulinNormethandrone 75 125 125 150 lt 1 1 5 lt 1 5a Dihydronormethandrone 15 25 50 75 lt 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 edit5a Dihydronorethandrolone 5a Dihydronandrolone 5a Dihydronorethisterone 5a DihydrolevonorgestrelReferences edit a b c Ojasoo T Delettre 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 Schjolberg 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 nbsp This pharmacology related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 5a Dihydronormethandrone amp oldid 1184633527, wikipedia, wiki, book, books, library,

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