Mestanolone An Overview of the Androgenic Steroid.pdf

Mestanolone, also known as methylandrostanolone or 17α-methyl-4,5α-dihydrotestosterone (17α-methyl-DHT), is a synthetic androgen and anabolic steroid (AAS) that has been used primarily in medical contexts but is now largely discontinued. Derived from dihydrotestosterone (DHT), it is notable for its strong androgenic properties with relatively weak anabolic effects. This article explores its chemical makeup, historical development, applications, pharmacology, potential risks, and current status.

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Mestanolone:AnOverviewoftheAndrogenicSteroid
HistoryandDevelopment
Mestanolone,alsoknownasmethylandrostanoloneor17α-methyl-4,5α-dihydrotestosterone
(17α-methyl-DHT),isasyntheticandrogenandanabolicsteroid(AAS)thathasbeenusedprimarily
inmedicalcontextsbutisnowlargelydiscontinued.Derivedfromdihydrotestosterone(DHT),itis
notableforitsstrongandrogenicpropertieswithrelativelyweakanaboliceffects.Thisarticle
exploresitschemicalmakeup,historicaldevelopment,applications,pharmacology,potentialrisks,
andcurrentstatus.
ChemicalStructureandProperties

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Mestanoloneisa17α-alkylatedderivativeofDHT,withthechemicalformulaC₂₀H₃₂O₂anda
molecularweightofapproximately304.47g/mol.ItssystematicIUPACnameis
(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodeca
hydro-1H-cyclopenta[a]phenanthren-3-one.Theadditionofamethylgroupatthe17αposition
enhancesitsoralbioavailability,allowingittobetakenbymouthwithoutrapiddegradationinthe
liver.UnlikeitsparentcompoundDHT,mestanoloneresistsmetabolismby3α-hydroxysteroid
dehydrogenase(3α-HSD)incertaintissues,contributingtoitspotencyasanandrogen.
Thisstructuralmodificationmakesmestanoloneincapableofaromatizationintoestrogen,
eliminatingrisksassociatedwithestrogenicactivity.Itisclassifiedasa3-oxo-5α-steroid,andits
stereochemistryisabsolute,withspecificchiralcentersthatdefineitsbiologicalactivity.
HistoricalDevelopment
Mestanolonewasfirstsynthesizedin1935alongsideotherearlysteroidslikemethyltestosterone
andmethandriol.ItwasdevelopedbythepharmaceuticalcompanyRousselinthe1950sand
introducedformedicalusebyaround1960underbrandnamessuchasAndrostalone,Ermalone,
Andoron,Mesanolon,andNotandron.InitiallymarketedinGermanyandotherregions,itwas
promotedasapotentanabolicagentforbuildingmuscleandtreatinghormonedeficiencies.
However,furtherresearchinthefollowingdecadesrevealedthatitsanaboliceffectswere
overstated,anditfunctionedprimarilyasanandrogen.Despitethis,mestanolonegainednotoriety
innon-medicalcontexts,particularlyinEastGermany'sstate-sponsoreddopingprogramduringthe
1970sand1980s.Athletes,includingOlympians,usedittoenhanceperformanceattributeslike
speed,strength,aggression,focus,endurance,andstressresilience,ratherthanforpuremuscle
growth.Bythelate20thcentury,itsmedicalapplicationsdiminished,anditwasdiscontinuedin
mostcountries,thoughitremainsavailableinJapan.
MedicalUses
Historically,mestanolonewasprescribedforconditionsinvolvingandrogendeficiency,suchas
malehypogonadism,wherethebodyproducesinsufficienttestosterone.Itwasadministeredorally,
oftenin25mgsublingualtabletsunderthebrandnameErmalone,topromotemasculinetraitsand
improvepsychologicalwell-being.Asanagonistoftheandrogenreceptor(AR)—thesametarget
asnaturalandrogensliketestosteroneandDHT—mestanolonehelpedalleviatesymptomslikelow
libido,fatigue,andmooddisturbances.
Unlikebroader-spectrumsteroids,itsweakanabolicprofilelimiteditsuseinmuscle-wasting
conditions.Today,itisrarelyemployedinmedicineduetotheavailabilityofsaferalternatives,butit
maystillbefoundinlimitedtherapeuticsettingsinJapanforsimilarindications.

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PharmacologyandMechanismofAction
Mestanoloneactsprimarilyasanandrogen,bindingtoandactivatingtheARintargettissues.This
leadstopronouncedmasculinizingeffects,includingenhancedsecondarysexualcharacteristics
andbehavioralchanges.Itsoralactivitystemsfromthe17α-methylgroup,whichprotectsitfrom
first-passmetabolismintheliver,thoughthisalsocontributestoitshepatotoxicity.
Inskeletalmuscle,mestanoloneisrapidlyinactivatedby3α-HSD,explainingitspooranabolic
potentialcomparedtootherAAS.Ithasnoestrogenicorprogestogenicactivity,asitcannotbe
convertedtoestrogenviaaromatase.Metabolizedmainlyintheliver,itisexcretedthroughurine.
Whileeffectiveforandrogenicpurposes,itsoverallprofilemakesitlessversatilethancompounds
liketestosterone.
SideEffectsandRisks
AswithotherAAS,mestanolonecarriesrisks,particularlyrelatedtoitsandrogenicpotencyand
17α-alkylation.Commonsideeffectsincludevirilizationsymptomssuchasacne,increasedbody
andfacialhairgrowth(hirsutism),scalphairloss,voicedeepening,andheightenedsexualdesire.
Inwomen,theseeffectscanbeirreversible.
Moreseriousconcernsinvolvehepatotoxicity,asthedrugcancauseliverdamage,including
elevatedliverenzymes,jaundice,andpotentiallytumorswithprolongeduse.Otherpotentialissues
includecardiovascularstrain,suchasalteredcholesterollevels,andsuppressionofnatural
testosteroneproduction,leadingtohypogonadismupondiscontinuation.Duetoits
non-aromatizablenature,itavoidsestrogen-relatedproblemslikegynecomastiaorfluidretention.
Usersshouldmonitorforsignsofprostateissues,moodchanges(e.g.,aggressionordepression),
andavoiditiftheyhavepre-existingliver,kidney,orprostateconditions.
LegalStatusandCurrentAvailability
Mestanoloneisclassifiedasacontrolledsubstanceinmanycountries,includingtheUnitedStates
(whereanabolicsteroidsfallunderScheduleIIIoftheControlledSubstancesAct)andmuchof
Europe.Non-medicaluse,suchasforperformanceenhancement,isgenerallyillegalandcanresult
inpenalties.ItisbannedbymajorsportsorganizationsliketheWorldAnti-DopingAgency(WADA)
duetoitshistoryindopingscandals.
Whilediscontinuedinmostmarkets,limitedavailabilitypersistsinJapanformedicalpurposes.In
researchsettings,itoccasionallyservesasareferencecompoundforstudyingandrogenreceptors,
butsaferalternativesarepreferred.

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Conclusion
Mestanolonerepresentsanearlychapterinthedevelopmentofsyntheticsteroids,valuedforits
androgenicstrengthbutlimitedbyweakanabolismandsignificantrisks.Onceatoolformedical
treatmentandathleticedge,ithasfadedfromprominenceamidconcernsoversafetyandethics.
AnyoneconsideringAASshouldconsulthealthcareprofessionals,asthepotentialforharmoften
outweighsbenefitsinnon-medicalscenarios.Ongoingresearchintohormonescontinuestoevolve,
offeringsaferoptionsforandrogen-relatedtherapies.