5α-Dihydronormethandrone

5α-Dihydronormethandrone
Clinical data

Other names	5α-DHNMT; RU-575; 17α-Methyl-4,5α-dihydro-19-nortestosterone; 17α-Methyl-5α-estran-17β-ol-3-one
Identifiers
IUPAC 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-one
CAS Number	6424-04-0^Y
PubChem CID	22792507
UNII	JHH2FT7BLU
Chemical and physical data
Formula	C₁₉H₃₀O₂
Molar mass	290.447 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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]

v
t
e
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.

References

^ ^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.
^ 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

Androgen receptor modulators

Agonists	Testosterone derivatives: 4-Androstenediol 4-Dehydroepiandrosterone (4-DHEA) 4-Hydroxytestosterone 4,17α-Dimethyltestosterone 5-Androstenedione 11-Ketotestosterone 11β-Hydroxyandrostenedione Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione) Androstenediol (5-androstenediol) Androstenediol 3β-acetate Androstenediol 17β-acetate Androstenediol diacetate Androstenediol dipropionate Androstenedione (4-androstenedione) Atamestane Boldenone Boldenone undecylenate Boldione (1,4-androstadienedione) Clostebol Clostebol acetate Clostebol caproate Clostebol propionate Cloxotestosterone Cloxotestosterone acetate Dehydroandrosterone DHEA (androstenolone, prasterone; 5-DHEA) DHEA enanthate (prasterone enanthate) DHEA sulfate Exemestane Formestane Plomestane Quinbolone Silandrone Testosterone^# (+dutasteride) Testosterone esters Polytestosterone phloretin phosphate 5α-Dihydrotestosterone derivatives: 1-Androstenediol 1-Androstenedione 1-Androsterone (1-andro, 1-DHEA) 1-Testosterone 3α-Androstanediol 5α-Androst-2-en-17-one 7β-Hydroxyepiandrosterone 11-Ketodihydrotestosterone Androsterone Bolazine Bolazine capronate Dihydroethyltestosterone Dihydrofluoxymesterone Dihydromethylandrostenediol Dihydrotestosterone (DHT) (androstanolone, stanolone) Dihydrotestosterone esters Drostanolone Drostanolone propionate Epiandrosterone Epitiostanol Mepitiostane Mesabolone Mesterolone Mesterolone cipionate Methyldiazinol Nisterime Nisterime acetate Prostanozol Stenbolone Stenbolone acetate Testifenon (testiphenon, testiphenone) 19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione) 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandiol dipropionate Bolandione (19-nor-4-androstenedione) Bolmantalate (nandrolone adamantoate) Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate) Methoxydienone (methoxygonadiene) Nandrolone Nandrolone esters Norclostebol Norclostebol acetate Normethandrone (methylestrenolone, normethisterone) Oxabolone Oxabolone cipionate (oxabolone cypionate) Trenbolone Trenbolone acetate Trenbolone enanthate Trenbolone hexahydrobenzylcarbonate Trenbolone undecanoate Trendione Trestolone (MENT) Trestolone acetate Trestolone enanthate 5α-Dihydro-19-nortestosterone derivatives: 5α-Dihydronandrolone 5α-Dihydrotrestolone 19-Norandrosterone 17α-Alkylated testosterone derivatives: Bolasterone Calusterone Chlorodehydromethylandrostenediol (CDMA) Chlorodehydromethyltestosterone (CDMT) Chloromethylandrostenediol (CMA) Enestebol Ethyltestosterone Fluoxymesterone Formebolone Hydroxystenozole Metandienone (methandrostenolone) Methandriol (methylandrostenediol) Methandriol bisenanthoyl acetate Methandriol diacetate Methandriol dipropionate Methandriol propionate Methylclostebol (chloromethyltestosterone) Methyltestosterone (+esterified estrogens) Methyltestosterone 3-hexyl ether Oxymesterone Penmesterol Tiomesterone 17α-Alkylated 5α-dihydrotestosterone derivatives: Androisoxazole Desoxymethyltestosterone Furazabol Mebolazine (dimethazine) Mestanolone Metenolone Metenolone acetate Metenolone enanthate Methasterone Methyl-1-testosterone Methylepitiostanol Methylstenbolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated 19-nortestosterone derivatives: Bolenol Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol Methyldienolone Methylhydroxynandrolone (MOHN, MHN) Metribolone Mibolerone Norboletone Norethandrolone Propetandrol RU-2309 Tetrahydrogestrinone 17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone 5α-Dihydronormethandrone 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone) 17α-Vinyl-19-nortestosterone derivatives: Vinyltestosterone 17α-Ethynyltestosterone derivatives: Danazol Ethinylandrostenediol Ethandrostate Ethisterone (ethynyltestosterone) 5α-Dihydro-17α-ethynyltestosterone derivatives: 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol Dihydroethisterone 17α-Ethynyl-19-nortestosterone derivatives: Δ⁴-Tibolone Desogestrel Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g., levonorgestrel butanoate) Lynestrenol Lynestrenol phenylpropionate Norethisterone Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate) Norgestrel Norgestrienone Quingestanol Quingestanol acetate Tibolone 5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel 5α-Dihydronorethisterone Progesterone derivatives: 6α-Methylprogesterone Medroxyprogesterone acetate Megestrol acetate Others/unsorted: 3-Keto-5α-abiraterone 5α-Androstane Alternariol Cl-4AS-1 Drupanol Trilostane ZM-182345
SARMsTooltip Selective androgen receptor modulator	Nonsteroidal: 198RL26 ACP-105 AC-262,536 Acetothiolutamide Acetoxolutamide Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4) BMS-564,929 DTIB Enobosarm (ostarine, MK-2866, GTx-024, S-22) FTBU-1 GLPG-0492 GSK2881078 GSK-4336A GSK-8698 LG121071 (LGD-121071) LGD-2226 LGD-2941 (LGD-122941) LGD-3303 LGD-4033 LY305 JNJ-26146900 JNJ-28330835 JNJ-37654032 OPK-88004 (LY-2452473, TT-701) ORM-11984 PF-06260414 R-1 RU-59063 S-1 S-23 S-40503 S-101479 Vosilasarm Steroidal: EM-9017 MK-0773 TFM-4AS-1 YK-11
Antagonists	Steroidal: 7α-Thioprogesterone 7α-Thiospironolactone 7α-Thiomethylspironolactone 11α-Hydroxyprogesterone 15β-Hydroxycyproterone acetate Abiraterone Abiraterone acetate Allyltestosterone Benorterone BOMT Canrenoic acid Canrenone Chlormadinone acetate Clascoterone Clometerone Cyproheptadine Cyproterone Cyproterone acetate Delanterone Delmadinone acetate Dicirenone Dienogest Drospirenone DU-41165 Edogestrone EM-4350 EM-5854 EM-5855 EM-6537 Epitestosterone Galeterone Guggulsterone Ludaterone Medrogestone Megestrol acetate Mespirenone Metogest Mexrenone Mifepristone Nomegestrol acetate Nordinone Osaterone Osaterone acetate Oxendolone Potassium canrenoate Promegestone Prorenone Rosterolone RU-15328 SC-5233 (spirolactone) Spironolactone Spirorenone Spiroxasone Topterone Trimegestone Trimethyltrienolone (R-2956) Zanoterone Nonsteroidal: 5N-Bicalutamide AA560 Antarlides Arabilin Apalutamide Atraric acid AZD-3514 Bakuchiol Bavdegalutamide BAY-1024767 Bicalutamide Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) BMS-501949 BMS-570511 BMS-641988 CH5137291 Cimetidine Cioteronel Cyanonilutamide Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide Inocoterone Inocoterone acetate Ketoconazole Ketodarolutamide Lavender oil LG-105 LG-120907 LGD-1331 Linuron Masofaniten Methiocarb N-Butylbenzenesulfonamide N-Desmethylapalutamide N-Desmethylenzalutamide Nilutamide ONC1-13B Pentomone PF-998425 Phenothrin Prochloraz Procymidone Proxalutamide Pyrilutamide Ralaniten (EPI-002) Ralaniten acetate (EPI-506) RD-162 Rezvilutamide Ro 2-7239 Ro 5-2537 RU-22930 RU-56187 RU-57073 RU-58642 RU-58841 Seviteronel Thalidomide Topilutamide (fluridil) Valproic acid Vinclozolin YM-580 YM-92088 YM-175735

GPRC6A

Agonists	Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

Progesterone receptor modulators

Agonists	Progesterone derivatives: 3β-Dihydroprogesterone 5α-Dihydroprogesterone 6α-Methylprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 16α-Hydroxyprogesterone 17α-Methyl-11-deoxycorticosterone acetate 20α-Dihydroprogesterone 20β-Dihydroprogesterone Dimepregnen Diosgenin P1-185 Progesterone Progesterone 3-acetyl enol ether Quingestrone Retroprogesterone derivatives: 20α-Dihydrodydrogesterone 20α-Dihydrotrengestone DU-41164 DU-41165 Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives: 6α-Methyl-17α-bromoprogesterone 15β-Hydroxycyproterone acetate 16-Methylene-17α-hydroxyprogesterone acetate 17α-Bromoprogesterone 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Anagestone Anagestone acetate Bromethenmadinone Bromethenmadinone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Chlormadinone caproate Chlormethenmadinone Chlormethenmadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cymegesolate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Fluorometholone Fluorometholone acetate Flumedroxone Flumedroxone acetate Fluoromedroxyprogesterone acetate Gestaclone Gestobutanoyl Haloprogesterone Hydromadinone Hydromadinone acetate Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Hydroxyprogesterone heptanoate benzilic acid hydrazone Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Medroxyprogesterone caproate Megestrol Megestrol acetate Megestrol caproate Melengestrol Melengestrol acetate Methenmadinone Methenmadinone acetate Methenmadinone caproate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone Triamcinolone acetonide 19-Norprogesterone derivatives: 17α-Methyl-19-norprogesterone 18-Methylsegesterone acetate 19-Norprogesterone Amadinone Amadinone acetate Demegestone Fluoro ethyl norprogesterone Fluoro furanyl norprogesterone Gestadienol Gestadienol acetate Gestonorone acetate (gestronol acetate) Gestonorone caproate (gestronol hexanoate) Gestronol (gestonorone) Nomegestrol Nomegestrol acetate Norgestomet ORG-2058 Oxogestone Oxogestone phenpropionate (xinogestone) Promegestone Segesterone Segesterone acetate (nestorone) Trimegestone Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone 6,6-Difluoronorethisterone acetate 17α-Allyl-19-nortestosterone Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethinylandrostenediol Ethandrostate Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g., levonorgestrel butanoate) Lynestrenol Lynestrenol phenylpropionate Metynodiol Metynodiol diacetate Norelgestromin Norethisterone (norethindrone) Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate) Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tibolone Tigestol Tosagestin; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandiol dipropionate Bolandione Dimethisterone Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol (ethylnandrol) Methyldienolone Metribolone (R-1881) Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norethandrolone Normethandrone (methylestrenolone, normethandrolone, normethisterone) RU-2309 Tetrahydrogestrinone Trenbolone (trienolone) Trenbolone esters (e.g., trenbolone acetate, trenbolone enanthate) Trendione Trestolone Trestolone acetate Spirolactone derivatives: Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate Prorenone SC-5233 (spirolactone) SC-8109 Spironolactone Spirorenone Nonsteroidal: 3,8-Dihydrodiligustilide LG-2527 LG-100128 Riligustilide RWJ-26819 RWJ-49853 RWJ-60130 Tanaproget ZM-182345 Unknown: ORG-47241 ORG-201745
Mixed (SPRMsTooltip Selective progesterone receptor modulators)	Steroidal: Dihydroethisterone 5α-Dihydrolevonorgestrel 5α-Dihydronorethisterone Asoprisnil Asoprisnil ecamate Guggulsterone J1042 LG-120838 Metapristone (RU-42633) Mifepristone (RU-486) ORF-9371 ORF-9326 ORG-31710 ORG-33628 RMI-12936 Telapristone Ulipristal acetate Vilaprisan ZK-137316 Nonsteroidal: Apigenin Kaempferol LG-120920 Naringenin PRA-910 Syringic acid
Antagonists	Steroidal: Aglepristone Lilopristone Lonaprisan Onapristone ORG-31710 ORG-31806 ORG-33628 RTI 3021–022 Toripristone Zanoterone Nonsteroidal: Darolutamide LG-001447 LG-100127 LG-100128 LG-120830 LG-121046 Valproic acid ZM-150271 ZM-172406

mPR
(PAQR)

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 11-Deoxycortisone (21-hydroxyprogesterone) 11-Deoxycortisol (17α,21-dihydroxyprogesterone) 17α-Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone
Antagonists	Mifepristone

See also: Receptor/signaling modulators; Progestogens and antiprogestogens; Androgen receptor modulators; Estrogen receptor modulators; List of progestogens

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Es krim bir dengan sebuah tart Es krim bir adalah sebuah jenis es krim yang disiapkan memakai bir sebagai bahan.[1][2] Es krim bir disiapkan memakai bir berwarna tua yang biasanya memiliki rasa yang berbeda dibandung bir yang disiapkan memakai bir yang berwarna muda. Alkohol dalam bir terkadang ada dalam es krim yang selesai dibuat, sementara persiapan lain meliputi memasak, yang dapat menghilangkan alkohol. Es krim soda dapat dibuat memakai bir. Referensi ^ Medrich, A. (2015)...

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5α-Dihydronormethandrone

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References

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