Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H32O2 |
Molecular Weight | 304.4669 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC(=O)CC[C@]34C
InChI
InChIKey=WYZDXEKUWRCKOB-YDSAWKJFSA-N
InChI=1S/C20H32O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h13,15-17,22H,4-12H2,1-3H3/t13-,15+,16-,17-,18-,19-,20-/m0/s1
DescriptionCurator's Comment: Description was created based on several sources, including https://www.steroid.com/Ermalone.php
Curator's Comment: Description was created based on several sources, including https://www.steroid.com/Ermalone.php
Mestanolone is an oral analogue of dihydrotestosterone. This steroid is a 17-alpha methylated form of this potent endogenous androgen, being essentially (in structure) to dihydrotestosterone what methyltestosterone is to testosterone. Overall, mestanolone has an activity profile not very dissimilar from the hormone it is derived from. Like dihydrotestosterone, mestanolone is primarily androgenic in nature, displaying a low level of anabolic activity. Both dihydrotestosterone and mestanolone are also devoid of estrogenic activity. Dihydrotestosterone was synthesized in 1935. After that 17-alpha-methylated version also appeared. This steroid was not frequently used in clinical medicine. It was produced under the name of ermalon for short period of time. Most studies involving mestanolone were carried out in the 1950s and 1960s. In the 1970s and 1980s it was used as part of the East German doping machine. Mestanolone was evaluated not for its anabolic ability but for its androgenic essence. It improved the functioning of the CNS and neuromuscular interaction. Athletes claimed that it did not make them huge, but gave them speed, strength, aggression, stamina and resistance to stress. Mestanolone is still valued as an oral androgen.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
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Histopathology as a tool for the evaluation of endocrine disruption in zebrafish (Danio rerio). | 2003 Apr |
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Efficient oxidizing methods for the synthesis of oxandrolone intermediates. | 2004 Aug |
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Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites. | 2005 Aug |
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Luteinizing hormone, follicle stimulating hormone, and gonadotropin releasing hormone mRNA expression of Xenopus laevis in response to endocrine disrupting compounds affecting reproductive biology. | 2006 Apr |
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Sex reversal in medaka treated in vitro with 17alpha-methyldihydrotestosterone during oocyte maturation. | 2006 Jan |
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Testosterone content of developing eggs and sex reversal in the medaka (Oryzias latipes). | 2006 Jan 1 |
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Endocrine disrupters with (anti)estrogenic and (anti)androgenic modes of action affecting reproductive biology of Xenopus laevis: I. Effects on sex steroid levels and biomarker expression. | 2007 Jan |
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Gonadal differentiation and hormonal sex reversal in Arctic charr (Salvelinus alpinus). | 2007 Sep 1 |
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Identification and quantification of metabolites common to 17alpha-methyltestosterone and mestanolone in horse urine. | 2007 Sep 21 |
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Hepatic gene expression profiling using GeneChips in zebrafish exposed to 17alpha-methyldihydrotestosterone. | 2008 Apr 28 |
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Detection of urinary metabolites common to structurally related 17alpha-alkyl anabolic steroids in horses and application to doping tests in racehorses: methandienone, methandriol, and oxymetholone. | 2008 Jun |
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Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry. | 2008 Sep |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
Dosages range from 10 mg to 30 mg a day for males for 6-8 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16466394
Intrafollicular oocytes of the medaka Oryzias latipes were incubated for about 10 h in the absence or the presence of Mestanolone at 1–100 ng/mL.
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DEA NO. |
4000
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WIKIPEDIA |
Designer-drugs-Mestanolone
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NCI_THESAURUS |
C2360
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C008376
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)