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Anabolic–androgenic steroid
Dimethyltrienolone Other names RU-2420; 7α あるふぁ ,17α あるふぁ -Dimethyltrenbolone; 7α あるふぁ ,17α あるふぁ -Dimethyl-δ でるた 9,11 -19-nortestosterone; 7α あるふぁ ,17α あるふぁ -Dimethylestra-4,9,11-trien-17β べーた -ol-3-one Routes of administration By mouth Drug class Androgen ; Anabolic steroid ; Progestogen
(7R ,8S ,13S ,14S ,17S )-17-hydroxy-7,13,17-trimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a ]phenanthren-3-one
CAS Number PubChem CID ChemSpider UNII ChEMBL Formula C 20 H 26 O 2 Molar mass 298.426 g·mol−1 3D model (JSmol )
C[C@@H]1CC2=CC(=O)CCC2=C3[C@@H]1[C@@H]4CC[C@]([C@]4(C=C3)C)(C)O
InChI=1S/C20H26O2/c1-12-10-13-11-14(21)4-5-15(13)16-6-8-19(2)17(18(12)16)7-9-20(19,3)22/h6,8,11-12,17-18,22H,4-5,7,9-10H2,1-3H3/t12-,17+,18-,19+,20+/m1/s1
Key:MEMDJKLEPFFNQS-ZGPIAVDESA-N
Dimethyltrienolone (developmental code name RU-2420 ) is a synthetic , orally active , and extremely potent anabolic–androgenic steroid (AAS) and 17α あるふぁ -alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use .[ 1] It has among the highest known affinity of any AAS for the androgen (and progesterone ) receptors ,[ 2] [ 3] and has been said to be perhaps the most potent AAS to have ever been developed.[ 1]
Dimethyltrienolone is an extremely potent agonist of the androgen and progesterone receptors and hence AAS and progestogen .[ 1] In animal bioassays , it was shown to possess more than 100 times the anabolic and androgenic potency of the reference AAS methyltestosterone .[ 1] The drug is not a substrate for 5α あるふぁ -reductase and so is not potentiated or inactivated in so-called "androgenic" tissues like the prostate gland or skin .[ 1] It is also not a substrate for aromatase and so has no estrogenic activity.[ 1] Due to its lack of estrogenicity, dimethyltrienolone has no propensity for causing estrogenic side effects like gynecomastia .[ 1] Because of its C17α あるふぁ methyl group and very high resistance to hepatic metabolism , dimethyltrienolone is said to be exceedingly hepatotoxic .[ 1]
Relative affinities (%) of dimethyltrienolone and related steroids[ 4] [ 5]
Compound
Chemical name
PR Tooltip Progesterone receptor
AR Tooltip Androgen receptor
ER Tooltip Estrogen receptor
GR Tooltip Glucocorticoid receptor
MR Tooltip Mineralocorticoid receptor
Testosterone
T
1.0
100
<0.1
0.17
0.9
Nandrolone
19-NT
20
154
<0.1
0.5
1.6
Trenbolone
∆9,11 -19-NT
74
197
<0.1
2.9
1.33
Trestolone
7α あるふぁ -Me-19-NT
50–75
100–125
?
<1
?
Normethandrone
17α あるふぁ -Me-19-NT
100
146
<0.1
1.5
0.6
Metribolone
∆9,11 -17α あるふぁ -Me-19-NT
208
204
<0.1
26
18
Mibolerone
7α あるふぁ ,17α あるふぁ -DiMe-19-NT
214
108
<0.1
1.4
2.1
Dimethyltrienolone
∆9,11 -7α あるふぁ ,17α あるふぁ -DiMe-19-NT
306
180
0.1
22
52
Values are percentages (%). Reference ligands (100%) were progesterone for the PR Tooltip progesterone receptor , testosterone for the AR Tooltip androgen receptor , estradiol for the ER Tooltip estrogen receptor , DEXA Tooltip dexamethasone for the GR Tooltip glucocorticoid receptor , and aldosterone for the MR Tooltip mineralocorticoid receptor .
Dimethyltrienolone, also known as 7α あるふぁ ,17α あるふぁ -dimethyl-δ でるた 9,11 -19-nortestosterone or as 7α あるふぁ ,17α あるふぁ -dimethylestra-4,9,11-trien-17β べーた -ol-3-one, as well as 7α あるふぁ ,17α あるふぁ -dimethyltrenbolone, is a synthetic estrane steroid and a 17α あるふぁ -alkylated derivative of nandrolone (19-nortestosterone).[ 1] It is the 7α あるふぁ ,17α あるふぁ -dimethyl derivative of trenbolone and the 7α あるふぁ -methyl derivative of metribolone ,[ 6] as well as the δ でるた 9,11 analogue of metribolone and the δ でるた 9,11 , 17α あるふぁ -methylated derivative of trestolone .[ 1]
Dimethyltrienolone was first described in 1967.[ 1] [ 7] It was never marketed for medical use.[ 1]
^ a b c d e f g h i j k l William Llewellyn (2009). Anabolics . Molecular Nutrition Llc. pp. 212–214. ISBN 978-0967930473 .
^ Waszkowycz B, Clark DE, Frenkel D, Li J, Murray CW, Robson B, Westhead DR (November 1994). "PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores". Journal of Medicinal Chemistry . 37 (23): 3994–4002. doi :10.1021/jm00049a019 . PMID 7966160 .
^ Loughney DA, Schwender CF (December 1992). "A comparison of progestin and androgen receptor binding using the CoMFA technique". Journal of Computer-Aided Molecular Design . 6 (6): 569–581. Bibcode :1992JCAMD...6..569L . doi :10.1007/bf00126215 . PMID 1291626 . S2CID 22004130 .
^ Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP (January 1980). "Steroid flexibility and receptor specificity". Journal of Steroid Biochemistry . 13 (1): 45–59. doi :10.1016/0022-4731(80)90112-0 . PMID 7382482 .
^ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry . 27 (1–3): 255–269. doi :10.1016/0022-4731(87)90317-7 . PMID 3695484 .
^ Rabe T, Kesel L, Runnebaum B (6 December 2012). "Antiprogestins" . In Ganten D, Pfaff D (eds.). Actions of Progesterone on the Brain . Springer Science & Business Media. pp. 17–. ISBN 978-3-642-69728-9 .
^ Mathieu J (1967). Proceedings of the International Symposium on Drug Research, Montreal, Canada, June 12-14, 1967 . Chemical Institute of Canada, Medical Chemistry Group, Montreal, Canada. p. 134.
AR Tooltip Androgen receptor
Agonists SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α あるふぁ -Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
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 べーた -Methyl-19-nortestosterone
11β べーた -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
Mixed (SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (PAQR Tooltip Progestin and adipoQ receptor )