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Anabolic–androgenic steroid
Dimethyltrienolone
Other names RU-2420; 7α,17α-Dimethyltrenbolone; 7α,17α-Dimethyl-δ9,11 -19-nortestosterone; 7α,17α-Dimethylestra-4,9,11-trien-17β-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-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]
Pharmacology
Pharmacodynamics
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-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
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-Me-19-NT
50–75
100–125
?
<1
?
Normethandrone
17α-Me-19-NT
100
146
<0.1
1.5
0.6
Metribolone
∆9,11 -17α-Me-19-NT
208
204
<0.1
26
18
Mibolerone
7α,17α-DiMe-19-NT
214
108
<0.1
1.4
2.1
Dimethyltrienolone
∆9,11 -7α,17α-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 .
Chemistry
Dimethyltrienolone, also known as 7α,17α-dimethyl-δ9,11 -19-nortestosterone or as 7α,17α-dimethylestra-4,9,11-trien-17β-ol-3-one, as well as 7α,17α-dimethyltrenbolone, is a
synthetic
estrane
steroid and a
17α-alkylated
derivative of
nandrolone (19-nortestosterone).
[1] It is the 7α,17α-dimethyl derivative of
trenbolone and the 7α-methyl derivative of
metribolone ,
[6] as well as the δ9,11
analogue of
metribolone and the δ9,11 , 17α-methylated derivative of
trestolone .
[1]
History
Dimethyltrienolone was first described in 1967.
[1]
[7] It was never marketed for medical use.
[1]
See also
References
^
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-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-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
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )