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5α-Dihydronormethandrone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
ChemSpider
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 nameRU-575), also known as17α-methyl-4,5α-dihydro-19-nortestosterone or as17α-methyl-5α-estran-17β-ol-3-one, is anandrogen/anabolic steroid and a likelymetabolite ofnormethandrone formed by5α-reductase.[1][2] Analogously to nandrolone and its 5α-reduced metabolite5α-dihydronandrolone, 5α-DHNMT shows reducedaffinity for theandrogen 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
CompoundPRTooltip Progesterone receptorARTooltip Androgen receptorERTooltip Estrogen receptorGRTooltip Glucocorticoid receptorMRTooltip Mineralocorticoid receptorSHBGTooltip Sex hormone-binding globulinCBGTooltip Corticosteroid binding globulin
Normethandrone75–125125–150<11–5<1??
5α-Dihydronormethandrone15–2550–75?<1???
Notes: Values are percentages (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,estradiol for theERTooltip estrogen receptor,dexamethasone for theGRTooltip glucocorticoid receptor, andaldosterone for theMRTooltip mineralocorticoid receptor.Sources: See template.

See also

[edit]

References

[edit]
  1. ^abcOjasoo 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


ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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