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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
Structure of MESTANOLONE

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

HIDE SMILES / InChI

Molecular Formula C20H32O2
Molecular Weight 304.4669
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Dosages range from 10 mg to 30 mg a day for males for 6-8 weeks
Route of Administration: Oral
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
S712YZ168E
Record Status Validated (UNII)
Record Version