# Mestanolone

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Mestanolone
> Markdown URL: https://mediated.wiki/source/Mestanolone.md
> Source: https://en.wikipedia.org/wiki/Mestanolone
> Source revision: 1336224538
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Chemical compound}}
{{Distinguish|Mesterolone}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 459508888
| IUPAC_name = (5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-hydroxy-10,13,17-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1''H''-cyclopenta[''a'']phenanthren-3-one
| image = Mestanolone Structural Formula V2.svg
| image_class = skin-invert-image
| width = 225px

<!--Clinical data-->
| tradename = Androstalone, Ermalone, others
| Drugs.com = {{drugs.com|international|mestanolone}}
| pregnancy_US = X
| legal_US = Schedule III
| routes_of_administration = [By mouth](/source/Oral_administration)
| class = [Androgen](/source/Androgen); [Anabolic steroid](/source/Anabolic_steroid)

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = [Liver](/source/Liver)
| elimination_half-life = 
| excretion = [Urine](/source/Kidney)

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 521-11-9
| ATC_prefix = None
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 261514
| PubChem = 10633
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10187
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S712YZ168E
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01533
| synonyms = RU-143; Methylandrostanolone; Methyldihydrotestosterone; Methyl-DHT; 17α-Methyl-4,5α-dihydrotestosterone; 17α-Methyl-DHT; 17α-Methyl-5α-androstan-17β-ol-3-one; 

<!--Chemical data-->
| C=20 | H=32 | O=2 
| SMILES = O=C2C[C@@H]1CC[C@@H]3[C@@H]([C@@]1(C)CC2)CC[C@]4([C@H]3CC[C@@]4(O)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WYZDXEKUWRCKOB-YDSAWKJFSA-N
}}

<!-- Definition and medical uses -->
'''Mestanolone''', also known as '''methylandrostanolone''' and sold under the brand names '''Androstalone''' and '''Ermalone''' among others, is an [androgen](/source/androgen) and [anabolic steroid](/source/anabolic_steroid) (AAS) medication which is mostly no longer used.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA775|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=775–}}</ref><ref name="IndexNominum2000">{{cite book | chapter = Mestanolone |title=Index Nominum 2000: International Drug Directory| chapter-url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA655 |year=2000 |publisher=Taylor & Francis |isbn=978-3-88763-075-1 |pages=655–}}</ref><ref name="Drugs.com" /><ref name="Llewellyn2009">{{cite book| vauthors = Llewellyn W |title= Anabolics |url= https://books.google.com/books?id=afKLA-6wW0oC |year=2009 |publisher=Molecular Nutrition Llc|isbn=978-0967930473|pages=241}}</ref> It is still available for use in [Japan](/source/Japan) however.<ref name="IndexNominum2000" /><ref name="Drugs.com" /> It is taken [by mouth](/source/oral_administration).<ref name="Llewellyn2009" />

<!-- Side effects and mechanism -->
[Side effect](/source/Side_effect)s of mestanolone include [symptom](/source/symptom)s of [masculinization](/source/virilization) like [acne](/source/acne), [increased hair growth](/source/hirsutism), [voice changes](/source/voice_deepening), and increased [sexual desire](/source/libido).<ref name="Llewellyn2009" /> It can also cause [liver damage](/source/hepatotoxicity).<ref name="Llewellyn2009" /> The drug is a [synthetic](/source/synthetic_compound) androgen and anabolic steroid and hence is an [agonist](/source/agonist) of the [androgen receptor](/source/androgen_receptor) (AR), the [biological target](/source/biological_target) of androgens like [testosterone](/source/testosterone) and [dihydrotestosterone](/source/dihydrotestosterone) (DHT).<ref name="Llewellyn2009" /><ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> It has strong [androgen](/source/androgen)ic effects and weak [anabolic](/source/anabolic) effects, which make it useful for producing masculine [psychological](/source/psychology) and [behavioral](/source/behavior) effects.<ref name="Llewellyn2009" /> The drug has no [estrogen](/source/estrogen_(medication))ic effects.<ref name="Llewellyn2009" />

<!-- History, society, and culture -->
Mestanolone was discovered in 1935 and was introduced for medical use in the 1950s.<ref name="pmid8674183" /><ref name="RuzickaGoldberg1935" /><ref name="pmid14086172" /><ref name="Llewellyn2009" /> In addition to its medical use, mestanolone has been used to [improve physique and performance](/source/performance-enhancing_substance).<ref name="Llewellyn2009" /> It was used in [East Germany](/source/East_Germany) in [Olympic](/source/Olympic_Games) [athlete](/source/athlete)s as part of a state-sponsored [doping](/source/Doping_in_sport) program in the 1970s and 1980s.<ref name="Llewellyn2009" /> The drug is a [controlled substance](/source/controlled_substance) in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2009" />

==Medical uses==
===Available forms===
Mestanolone was available in the form of 25&nbsp;mg [sublingual](/source/sublingual_administration) [tablet](/source/tablet_(pharmacy))s (brand name Ermalone).<ref name="Krüskemper2013">{{cite book | vauthors = Krüskemper HL |title=Anabolic Steroids|url=https://books.google.com/books?id=4xIlBQAAQBAJ&pg=PA196|date=22 October 2013|publisher=Elsevier|isbn=978-1-4832-6504-9|pages=196–}}</ref>

==Side effects==
{{See also|Anabolic steroid#Adverse effects}}

[Side effect](/source/Side_effect)s of mestanolone include [virilization](/source/virilization) and [hepatotoxicity](/source/hepatotoxicity) among others.<ref name="Llewellyn2009" />

==Pharmacology==
===Pharmacodynamics===
Mestanolone is an AAS, with both [androgen](/source/androgen)ic and [anabolic](/source/anabolic) effects.<ref name="Llewellyn2009" /> It is very similar in its effects to [androstanolone](/source/androstanolone) (dihydrotestosterone; DHT), and can be thought of as an [orally active](/source/oral_administration) version of this AAS.<ref name="Llewellyn2009" /> Due to inactivation by [3α-hydroxysteroid dehydrogenase](/source/3%CE%B1-hydroxysteroid_dehydrogenase) (3α-HSD) in [skeletal muscle](/source/skeletal_muscle), mestanolone is described as a very poor [anabolic](/source/anabolic) agent, similarly to androstanolone and [mesterolone](/source/mesterolone).<ref name="Llewellyn2009" /> As mestanolone is [5α-reduced](/source/5%CE%B1-reductase), it cannot be [aromatized](/source/aromatase) and hence has no propensity for [estrogen](/source/estrogen)ic [side effect](/source/side_effect)s such as [gynecomastia](/source/gynecomastia).<ref name="Llewellyn2009" /> The drug also has no [progestogen](/source/progestogen)ic activity.<ref name="Llewellyn2009" /> Like other 17α-alkylated AAS, mestanolone is [hepatotoxic](/source/hepatotoxic).<ref name="Llewellyn2009" />

===Pharmacokinetics===
Due to its C17α [methyl group](/source/methyl_group), unlike androstanolone, mestanolone is [orally active](/source/oral_administration).<ref name="Llewellyn2009" />

==Chemistry==
{{See also|List of androgens/anabolic steroids}}

Mestanolone, also known as 17α-methyl-4,5α-dihydrotestosterone (17α-methyl-DHT) or as 17α-methyl-5α-androstan-17β-ol-3-one, is a [synthetic](/source/synthetic_compound) [androstane](/source/androstane) [steroid](/source/steroid) and a [17α-alkylated](/source/17%CE%B1-alkylated_AAS) [derivative](/source/chemical_derivative) of [dihydrotestosterone](/source/dihydrotestosterone) (DHT).<ref name="Elks2014" /><ref name="Llewellyn2009" /> It differs from DHT only by the presence of the [methyl group](/source/methyl_group) at the C17α position.<ref name="Elks2014" /><ref name="Llewellyn2009" /> Close synthetic relatives of mestanolone include [oxandrolone](/source/oxandrolone) (2-oxa-17α-methyl-DHT), [oxymetholone](/source/oxymetholone) (2-hydroxymethylene-17α-methyl-DHT), and [stanozolol](/source/stanozolol) (a derivative of 17α-methyl-DHT (mestanolone) with a [pyrazole](/source/pyrazole) [ring](/source/ring_(chemistry)) fused to the A ring).<ref name="Elks2014" /><ref name="Llewellyn2009" />

===Synthesis===
The chemical synthesis of mestanolone was reported:<ref>廖俊, et al. CN109627273 (2019 to HUAZHONG PHARMACEUTICAL CO Ltd).</ref> Although the Lednicer book method uses DHEA as the starting material,<ref>{{cite book | vauthors=((Lednicer, D.)) | date= 2011 | title=Steroid chemistry at a glance | publisher=Wiley | series=Chemistry at a glance | edition=1. publ | isbn=9780470660843}}</ref> [androstenedione](/source/androstenedione) is cheaper and more readily available.

center|500px|class=skin-invert-image

The reaction of [Androstenedione](/source/Androstenedione) [63-05-8] ('''1''') with [triethyl orthoformate](/source/triethyl_orthoformate) convers the enone into the corresponding enol ether, 3-Ethoxyandrosta-3,5-dien-17-one [972-46-3] ('''2'''). Grignard addition of methyl magnesium halide gives ('''3'''). [Catalytic hydrogenation](/source/Catalytic_hydrogenation) reduces the C5=C6 olefin giving ('''4'''). Hydrolysis of the product in aqueous acid completed the synthesis of mestanolone ('''5''').
===Applications===
Mestanolone is used in the chemical synthesis of [Methyl-1-testosterone](/source/Methyl-1-testosterone), which in-turn is used to make [oxandrolone](/source/oxandrolone).

Mestanolone is also used to make [Oxymesterone](/source/Oxymesterone), [Methyldiazirinol](/source/Methyldiazirinol) & [Furazabol](/source/Furazabol).

Another use is in the synthesis of [Oxymetholone](/source/Oxymetholone), a compound which itself finds use in the synthesis of [stanozolol](/source/stanozolol), [Cyanostane](/source/Cyanostane), [Androisoxazole](/source/Androisoxazole) & [Methasterone](/source/Methasterone).

==History==
Mestanolone was first [synthesized](/source/chemical_synthesis) in 1935 along with [methyltestosterone](/source/methyltestosterone) and [methandriol](/source/methandriol).<ref name="pmid8674183">{{cite journal | vauthors = Schänzer W | title = Metabolism of anabolic androgenic steroids | journal = Clinical Chemistry | volume = 42 | issue = 7 | pages = 1001–1020 | date = July 1996 | pmid = 8674183 | doi = 10.1093/clinchem/42.7.1001 | doi-access = free }}</ref><ref name="RuzickaGoldberg1935">{{cite journal| vauthors = Ruzicka L, Goldberg MW, Rosenberg HR |title=Sexualhormone X. Herstellung des 17-Methyl-testosterons und anderer Androsten- und Androstanderivate. Zusammenhänge zwischen chemischer Konstitution und männlicher Hormonwirkung|journal=Helvetica Chimica Acta|volume=18|issue=1|year=1935|pages=1487–1498|issn=0018-019X|doi=10.1002/hlca.193501801203}}</ref> It was developed by [Roussel](/source/Roussel_Uclaf) in the 1950s and was introduced for medical use, under the brand names Androstalone and Ermalone, by at least 1960.<ref name="Llewellyn2009" /><ref name="pmid13800998">{{cite journal | vauthors = Bishop PM | title = Male sex hormones | journal = British Medical Journal | volume = 1 | issue = 5167 | pages = 184–186 | date = January 1960 | pmid = 13800998 | pmc = 1966335 | doi = 10.1136/bmj.1.5167.184 }}</ref><ref name="pmid14086172">{{cite journal | vauthors = Arnold A, Potts GO, Beyler AL | title = The Ratio of Anabolic to Androgenic Activity of 7: 17-Dimethyltestosterone, Oxymesterone, Mestanolone and Fluoxymesterone | journal = The Journal of Endocrinology | volume = 28 | pages = 87–92 | date = December 1963 | pmid = 14086172 | doi = 10.1677/joe.0.0280087 }}</ref> It was marketed in [Germany](/source/Germany).<ref name="Llewellyn2009" /> The drug was originally thought to be a potent [anabolic](/source/anabolic) agent, but subsequent research showed that it actually has relatively weak anabolic effects and is mostly an androgen.<ref name="Llewellyn2009" /> Mestanolone was used as a [doping agent](/source/doping_agent) in [athlete](/source/athlete)s competing in the [Olympics](/source/Olympics) from [East Germany](/source/East_Germany) due to a state-sponsored doping program in the 1970s and 1980s.<ref name="Llewellyn2009" /> Its value is said to have been less as a muscle-builder and more as an androgen in the [central nervous system](/source/central_nervous_system) and [neuromuscular interaction](/source/neuromuscular_junction), improving speed, strength, [aggression](/source/aggression), [focus](/source/attention), [endurance](/source/endurance), and [stress resilience](/source/stress_resilience).<ref name="Llewellyn2009" /> Today, mestanolone has mostly been discontinued in medicine, though it is still available in [Japan](/source/Japan).<ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="Llewellyn2009" />

==Society and culture==
===Generic names===
''Mestanolone'' is the [generic name](/source/generic_term) of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}, and {{abbrlink|JAN|Japanese Accepted Name}}.<ref name="Elks2014" /><ref name="ChemIDplus">{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/#tab/sidsrcname=ChemIDplus&query=521-11-9&input_type=text| work = ChemIDplus | title = Mestanolone &#91;INN:BAN:JAN&#93; | publisher = U.S. National Library of Medicine }}</ref>

===Brand names===
Mestanolone was marketed under the brand names Andoron, Androstalone, Ermalone, Mesanolon, and Notandron among many others.<ref name="Llewellyn2009" /><ref name="IndexNominum2000" /><ref name="Negwer1987">{{cite book| vauthors = Negwer M |title=Organic-chemical Drugs and Their Synonyms: (an International Survey)|url=https://books.google.com/books?id=k6fwAAAAMAAJ|year=1987|publisher=VCH Publishers|isbn=978-0-89573-552-2|quote=Anavormol, Andoron, Androne, Androstalone, Antalon “Kobayashi K.”, Assimil, Ermalone, Etnabolate, Hermalone-Glosset, Macrobin (Tabl. -- Syrup), Mesanolon, Mestalone, Mestanolone”, Methyantalon, Methybol, 172-Methylandrostanolone, Preroide,. 1045.}}</ref><ref name="Drugs.com">{{Cite web|url=https://www.drugs.com/international/mestanolone.html|title = S1. Anabolic Agents | work = Drugs in Sport: Anti-Doping Prohibited List | via = Drugs.com }}</ref>

===Availability===
Mestanolone has mostly been discontinued but remains available in [Japan](/source/Japan).<ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="Llewellyn2009" />

==References==
{{Reflist}}

{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}

Category:Abandoned drugs
Category:Tertiary alcohols
Category:Androgens
Category:Androstanes
Category:Hepatotoxins
Category:Human drug metabolites
Category:Ketones

---
Adapted from the Wikipedia article [Mestanolone](https://en.wikipedia.org/wiki/Mestanolone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Mestanolone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.