{{Short description|Androgen and anabolic steroid}} {{Drugbox | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 4(8''S'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-Hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[a]phenanthren-3-one | image = Metandienone.svg | image_class = skin-invert-image | width = 225px

<!--Clinical data--> | tradename = Dianabol, others | pregnancy_US = X

| legal_AU = S4 | legal_BR = C5 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}</ref> | legal_CA = Schedule IV | legal_US = Schedule III | legal_status = | routes_of_administration = By mouth, intramuscular injection (veterinary)<ref name="Llewellyn2011" /> | class = Androgen; Anabolic steroid

<!--Pharmacokinetic data--> | bioavailability = High | protein_bound = | metabolism = Hepatic | elimination_half-life = 3–6 hours<ref name="Llewellyn2011" /><ref name="RuizStrain2011">{{cite book| vauthors = Ruiz P, Strain EC |title=Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook|url=https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358|year=2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-60547-277-5|pages=358–}}</ref> | excretion = Urine

<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 72-63-9 | ATC_prefix = A14 | ATC_suffix = AA03 | ATC_supplemental = {{ATC|D11|AE01}} | PubChem = 6300 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB13586 | KEGG = D00389 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6061 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = COZ1R7EOCC | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1418176 | synonyms = Methandienone; Methandrostenolone; Methandrolone; Dehydromethyltestosterone; Methylboldenone; Perabol; Ciba-17309-Ba; TMV-17; NSC-51180; NSC-42722; 17α-Methyl-δ<sup>1</sup>-testosterone; 17β-Hydroxy-17α-methylandrosta-1,4-dien-3-one; 17α-Methylandrost-1,4-dien-17β-ol-3-one

<!--Chemical data--> | C=20 | H=28 | O=2 | SMILES = O=C\1\C=C/[C@]4(/C(=C/1)CC[C@@H]3[C@@H]4CC[C@]2([C@H]3CC[C@@]2(O)C)C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C20H28O2/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/h6,9,12,15-17,22H,4-5,7-8,10-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XWALNWXLMVGSFR-HLXURNFRSA-N }}

'''Metandienone''', also known as '''methandienone''' or '''methandrostenolone''' and sold under the brand name '''Dianabol''' ('''D-Bol''') among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer prescribed.<ref name="IndexNominum2000">{{cite book | author = Swiss Pharmaceutical Society | chapter = Metandienone | title = Index Nominum 2000: International Drug Directory | chapter-url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PT660 | year = 2000 | publisher = Taylor & Francis | isbn = 978-3-88763-075-1 | page = 660 }}</ref><ref name="MortonHall2012">{{cite book | vauthors = Morton IK, Hall JM | title = Concise Dictionary of Pharmacological Agents: Properties and Synonyms | url = https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA177 | date = 6 December 2012 | publisher = Springer Science & Business Media | isbn = 978-94-011-4439-1 | pages = 177– }}</ref><ref name="Llewellyn2011">{{cite book | vauthors = Llewellyn W | title = Anabolics | url = https://books.google.com/books?id=afKLA-6wW0oC&pg=PT444 | year = 2011 | publisher = Molecular Nutrition Llc | isbn = 978-0-9828280-1-4 | pages=444–454, 533 }}</ref><ref name="Drugs.com">{{cite web | url = https://www.drugs.com/international/metandienone.html | title = Metandienone | work = drugs.com }}</ref> It is also used non-medically for physique- and performance-enhancing purposes.<ref name="Llewellyn2011" /> It is often taken by mouth.<ref name="Llewellyn2011" />

Side effects of metandienone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire, estrogenic effects like fluid retention and breast enlargement, and liver damage.<ref name="Llewellyn2011" /> The drug is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT), and has strong anabolic effects and moderate androgenic effects.<ref name="Llewellyn2011" /> It also has moderate estrogenic effects.<ref name="Llewellyn2011" />

Metandienone was originally developed in 1955 by CIBA and marketed in Germany and the United States.<ref name="Llewellyn2011" /><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=PA781 | date = 14 November 2014 | publisher = Springer | isbn = 978-1-4757-2085-3 | pages = 781– }}</ref><ref name="IndexNominum2000" /><ref name="Yesali_1990">{{cite journal | vauthors = Yesalis CE, Anderson WA, Buckley WE, Wright JE | title = Incidence of the nonmedical use of anabolic-androgenic steroids | journal = NIDA Research Monograph | volume = 102 | pages = 97–112 | year = 1990 | pmid = 2079979 | url = http://www.drugabuse.gov/pdf/monographs/102.pdf | access-date = 2007-09-26 | archive-date = 2007-10-31 | archive-url = https://web.archive.org/web/20071031080129/http://www.drugabuse.gov/pdf/monographs/102.pdf | url-status = dead }}</ref><ref name="Fair_1993">{{cite journal| vauthors = Fair JD |title=Isometrics or Steroids? Exploring New Frontiers Of Strength in the Early 1960s |journal=Journal of Sport History |volume=20 |issue=1 |pages=1–24 |year=1993 |url=http://www.la84foundation.org/SportsLibrary/JSH/JSH1993/JSH2001/jsh2001b.pdf |url-status=dead |archive-url=https://web.archive.org/web/20080528195958/http://www.la84foundation.org/SportsLibrary/JSH/JSH1993/JSH2001/jsh2001b.pdf |archive-date=2008-05-28 }}</ref> As the CIBA product Dianabol, metandienone quickly became the first widely used AAS among professional and amateur athletes, and remains the most common orally active AAS for non-medical use.<ref name="Yesalis_2002">{{cite journal | vauthors = Yesalis C, Bahrke M | year = 2002 | title = History of Doping in Sport | url = http://library.la84.org/SportsLibrary/ISS/ISS2401/ISS2401e.pdf | journal = International Sports Studies | volume = 24 | pages = 42–76 | access-date = 2017-01-14 | archive-url = https://web.archive.org/web/20171123053107/http://library.la84.org/SportsLibrary/ISS/ISS2401/ISS2401e.pdf | archive-date = 2017-11-23 | url-status = dead }}</ref><ref name="Yesali_1990" /><ref>{{cite book|url=https://archive.org/details/bub_gb_DXTysiS5ndQC|page=[https://archive.org/details/bub_gb_DXTysiS5ndQC/page/n37 29]|quote=dianabol history.|title=Anabolic Steroid Abuse| vauthors = Lin GC, Erinoff L |date=1996-07-01|publisher=DIANE Publishing|isbn=978-0-7881-2969-8}}</ref><ref>{{cite web | url = http://www.alanaragonblog.com/wp-content/uploads/2014/11/Aug-2014-AARR-Eric-Helms-Article.pdf | title = What can be achieved as a natural bodybuilder?| vauthors = Helms E |date=August 2014|website=Alan Aragon's Research Review|publisher=Alan Aragon}}</ref> It is currently a controlled substance in the United States<ref>{{cite book | publisher = United States Drug Enforcement Administration | title = Controlled Substances, Alphabetical Order | url = http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf | access-date = 2013-04-06 | archive-date = 2016-04-17 | archive-url = https://web.archive.org/web/20160417085659/http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf | url-status = dead }}</ref> and United Kingdom<ref>{{cite web | url=https://www.gov.uk/government/publications/controlled-drugs-list--2/list-of-most-commonly-encountered-drugs-currently-controlled-under-the-misuse-of-drugs-legislation|title=List of most commonly encountered drugs currently controlled under the misuse of drugs legislation | website=www.gov.uk|access-date=2017-01-14}}</ref> and remains popular among bodybuilders. Metandienone is readily available without a prescription in certain countries such as Mexico, and is also manufactured in some Asian countries.<ref name="Drugs.com" />

==Medical uses== Metandienone was formerly approved and marketed as a form of androgen replacement therapy for the treatment of hypogonadism in men, but has since been discontinued and withdrawn in most countries, including in the United States.<ref name="Barceloux2012">{{cite book | vauthors = Barceloux DG | title = Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants|url=https://books.google.com/books?id=9JLiJcjdqkcC&pg=PA275|date=3 February 2012|publisher=John Wiley & Sons|isbn=978-1-118-10605-1|pages=275–}}</ref><ref name="IndexNominum2000" /><ref name="Drugs.com"/>

It was given at a dosage of 5 to 10&nbsp;mg/day in men and 2.5&nbsp;mg/day in women.<ref name="Fruehan1963">{{cite journal | vauthors = Fruehan AE, Frawley TF | title = Current status of anabolic steroids | journal = JAMA | volume = 184 | issue = 7 | pages = 527–532 | date = May 1963 | pmid = 13945852 | doi = 10.1001/jama.1963.03700200049009 }}</ref><ref name="Pharmind1978">{{cite book|title=ABPI Data Sheet Compendium|url=https://books.google.com/books?id=YvS3AAAAIAAJ|year=1978|publisher=Pharmind Pub.}}</ref><ref name="Llewellyn2011" />

{{Androgen replacement therapy formulations and dosages used in men}}

===Available forms=== Metandienone was provided in the form of 2.5, 5 and 10&nbsp;mg oral tablets.<ref name="NDCD1982">{{cite book|title=National Drug Code Directory|url=https://books.google.com/books?id=n1FqfT-jEagC&pg=PA642|year=1982|publisher=Consumer Protection and Environmental Health Service, Public Health Service, U.S. Department of Health, Education, and Welfare|pages=642–}}</ref><ref>{{cite book|title=Federal Register|url=https://books.google.com/books?id=dxNAxmL0SvkC&pg=PA2208|date=18 January 1983|publisher=Office of the Federal Register, National Archives and Records Service, General Services Administration|pages=2208–2209}}</ref><ref name="APA1974">{{cite book|title=The National Formulary ...|url=https://books.google.com/books?id=Mu4jAQAAMAAJ|year=1974|publisher=American Pharmaceutical Association|quote=Tablets available — Methandrostenolone Tablets usually available contain the following amounts of methandrostenolone: 2.5 and 5 mg.}}</ref><ref name="Llewellyn2011" />

==Non-medical uses== Metandienone is used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.<ref name="Llewellyn2011" /> It is said to be the most widely used AAS for such purposes both today and historically.<ref name="Llewellyn2011" />

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

Androgenic side effects such as oily skin, acne, seborrhea, increased facial/body hair growth, scalp hair loss, and virilization may occur.<ref name="Llewellyn2011" /> Estrogenic side effects such as gynecomastia and fluid retention can also occur.<ref name="Llewellyn2011" /> Case reports of gynecomastia exist.<ref name="Dorfman2016">{{cite book| vauthors = Dorfman RI |title=Steroidal Activity in Experimental Animals and Man|url=https://books.google.com/books?id=uizgBAAAQBAJ&pg=PA70|date=5 December 2016|publisher=Elsevier Science|isbn=978-1-4832-7300-6|pages=70–}}</ref><ref name="Laron1962">{{cite journal | vauthors = Laron Z | title = Breast development induced by methandrostenolone (Dianabol) | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 22 | issue = 4 | pages = 450–452 | date = April 1962 | pmid = 14462467 | doi = 10.1210/jcem-22-4-450 }}</ref> As with other 17α-alkylated steroids, methandienone poses a risk of hepatotoxicity and use over extended periods of time can result in liver damage without appropriate precautions.<ref name="Llewellyn2011" />

==Pharmacology==

===Pharmacodynamics=== {{Relative androgenic to anabolic activity in animals}}

Methandienone binds to and activates the androgen receptor (AR) in order to exert its effects.<ref>{{cite journal | vauthors = Roselli CE | title = The effect of anabolic-androgenic steroids on aromatase activity and androgen receptor binding in the rat preoptic area | journal = Brain Research | volume = 792 | issue = 2 | pages = 271–6 | date = May 1998 | pmid = 9593936 | doi = 10.1016/S0006-8993(98)00148-6 | s2cid = 29441013 }}</ref> These include dramatic increases in protein synthesis, glycogenolysis, and muscle strength over a short space of time.{{medcn|date=April 2014}} While it can be metabolized by 5α-reductase into methyl-1-testosterone (17α-methyl-δ<sup>1</sup>-DHT), a more potent AAS, the drug has extremely low affinity for this enzyme and methyl-1-testosterone is thus produced in only trace amounts.<ref name="Llewellyn2011" /><ref name="pmid2031859">{{cite journal | vauthors = Schänzer W, Geyer H, Donike M | title = Metabolism of metandienone in man: identification and synthesis of conjugated excreted urinary metabolites, determination of excretion rates and gas chromatographic-mass spectrometric identification of bis-hydroxylated metabolites | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 38 | issue = 4 | pages = 441–64 | date = April 1991 | pmid = 2031859 | doi = 10.1016/0960-0760(91)90332-y | s2cid = 20197705 }}</ref> As such, 5α-reductase inhibitors like finasteride and dutasteride do not reduce the androgenic effects of metandienone.<ref name="Llewellyn2011" /> Nonetheless, while the ratio of anabolic to androgenic activity of metandienone is improved relative to that of testosterone, the drug does still possess moderate androgenic activity and is capable of producing severe virilization in women and children.<ref name="Llewellyn2011" /> As such, it is only really commonly used in men.<ref name="Llewellyn2011" />

Metandienone is a substrate for aromatase and can be metabolized into the estrogen methylestradiol (17α-methylestradiol).<ref name="Llewellyn2011" /> While the rate of aromatization is reduced relative to that for testosterone or methyltestosterone, the estrogen produced is metabolism-resistant and hence metandienone retains moderate estrogenic activity.<ref name="Llewellyn2011" /> As such, it can cause side effects such as gynecomastia and fluid retention.<ref name="Llewellyn2011" /> The co-administration of an antiestrogen such as an aromatase inhibitor like anastrozole or a selective estrogen receptor modulator like tamoxifen can reduce or prevent such estrogenic side effects.<ref name="Llewellyn2011" /> Metandienone has no progestogenic activity.<ref name="Llewellyn2011" />

As with other 17α-alkylated AAS, metandienone may be hepatotoxic, especially with prolonged use of high doses.<ref name="Llewellyn2011" />

===Pharmacokinetics=== Metandienone has high oral bioavailability.<ref name="Llewellyn2011" /> It has very low affinity for human serum sex hormone-binding globulin (SHBG), about 10% of that of testosterone and 2% of that of DHT.<ref name="pmid6539197">{{cite journal | vauthors = Saartok T, Dahlberg E, Gustafsson JA | title = Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin | journal = Endocrinology | volume = 114 | issue = 6 | pages = 2100–6 | date = June 1984 | pmid = 6539197 | doi = 10.1210/endo-114-6-2100 }}</ref> The drug is metabolized in the liver by 6β-hydroxylation, 3α- and 3β-oxidation, 5β-reduction, 17-epimerization, and conjugation among other reactions.<ref name="pmid2031859" /> Unlike methyltestosterone, owing to the presence of its C1(2) double bond, metandienone does not produce 5α-reduced metabolites.<ref name="pmid2031859" /><ref name="Llewellyn2011" /><ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–21 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> The elimination half-life of metandienone is about 3 to 6&nbsp;hours.<ref name="Llewellyn2011" /><ref name="RuizStrain2011" /> It is eliminated in the urine.<ref name="pmid2031859" />

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

Metandienone, also known as 17α-methyl-δ<sup>1</sup>-testosterone or as 17α-methylandrost-1,4-dien-17β-ol-3-one, is a synthetic androstane steroid and a 17α-alkylated derivative of testosterone.<ref name="Elks2014" /> It is a modification of testosterone with a methyl group at the C17α position and an additional double bond between the C1 and C2 positions.<ref name="Elks2014" /> The drug is also the 17α-methylated derivative of boldenone (δ<sup>1</sup>-testosterone) and the δ<sup>1</sup> analogue of methyltestosterone (17α-methyltestosterone).<ref name="Elks2014" />

===Detection in body fluids=== Metandienone is subject to extensive hepatic biotransformation by a variety of enzymatic pathways. The primary urinary metabolites are detectable for up to 3 days, and a recently discovered hydroxymethyl metabolite is found in urine for up to 19 days after a single 5&nbsp;mg oral dose.<ref>{{cite journal | vauthors = Schänzer W, Geyer H, Fusshöller G, Halatcheva N, Kohler M, Parr MK, Guddat S, Thomas A, Thevis M | title = Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine | journal = Rapid Communications in Mass Spectrometry | volume = 20 | issue = 15 | pages = 2252–8 | year = 2006 | pmid = 16804957 | doi = 10.1002/rcm.2587 | bibcode = 2006RCMS...20.2252S }}</ref> Several of the metabolites are unique to metandienone. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry.<ref>{{cite book | vauthors = Baselt R | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 8th | publisher = Biomedical Publications | location = Foster City, CA | year = 2008 | pages = 952–4 }}</ref><ref>{{cite journal | vauthors = Fragkaki AG, Angelis YS, Tsantili-Kakoulidou A, Koupparis M, Georgakopoulos C | title = Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 115 | issue = 1–2 | pages = 44–61 | date = May 2009 | pmid = 19429460 | doi = 10.1016/j.jsbmb.2009.02.016 | s2cid = 10051396 }}</ref>

==History== Metandienone was first described in 1955.<ref name="Llewellyn2011" /> It was synthesized by researchers at the CIBA laboratories in Basel, Switzerland. CIBA filed for a U.S. patent in 1957,<ref>{{cite patent | country = US | number = 2900398 |status = granted | title = Process for the manufacture of steroid dehydrogenation products | gdate = 18 August 1959 | inventor = Wettstein A, Hunger A, Meystre C, Ehmann L | assign1 = Ciba Pharmaceutical Products, Inc. }}</ref> and began marketing the drug as Dianabol in 1958 in the U.S.<ref name="Llewellyn2011" /><ref name=":3">{{cite news | vauthors = Chaney M | url = http://www.nydailynews.com/sports/football/dianabol-widely-steroid-turns-50-year-article-1.292864 | title = Dianabol, the first widely used steroid, turns 50 | newspaper = NY Daily News | date = 16 June 2008 | access-date = 2017-01-14 }}</ref> It was initially prescribed to burn victims and the elderly. It was also prescribed off-label as a pharmaceutical performance enhancement to weight lifters and other athletes.<ref name="Peters_2005">{{cite news | url = http://www.slate.com/articles/sports/sports_nut/2005/02/the_man_behind_the_juice.html | title = The Man Behind the Juice | vauthors = Peters J | date = 2005-02-18 | newspaper = Slate | issn = 1091-2339 | access-date = 2017-01-14 }}</ref> Early adopters included players for Oklahoma University and San Diego Chargers head coach Sid Gillman, who administered Dianabol to his team starting in 1963.<ref>{{cite web | vauthors = Quinn TJ | url = http://www.espn.com/espn/otl/news/story?id=3866837 | title = OTL: Football's first steroids team? The '63 Chargers | date = 2009-02-01 | work = ESPN | access-date = 2017-01-14 }}</ref>

After the Kefauver Harris Amendment was passed in 1962, the U.S. FDA began the DESI review process to ensure the safety and efficacy of drugs approved under the more lenient pre-1962 standards, including Dianabol.<ref>{{cite journal| vauthors = Fourcroy J |title=Designer steroids: past, present and future|journal=Current Opinion in Endocrinology, Diabetes and Obesity|volume=13|issue=3|pages=306–309|doi=10.1097/01.med.0000224812.46942.c3|year=2006|s2cid=87333977 }}</ref> In 1965, the FDA pressured CIBA to further document its legitimate medical uses, and re-approved the drug for treating post-menopausal osteoporosis and pituitary-deficient dwarfism.<ref name="Llewellyn_2011">{{cite book | url = https://books.google.com/books?id=afKLA-6wW0oC&q=dianabol+ciba+fda&pg=PT446 | title = Anabolics | vauthors = Llewellyn W | date=2011-01-01 | publisher = Molecular Nutrition Llc | isbn = 978-0-9828280-1-4 }}</ref> After CIBA's patent exclusivity period lapsed, other manufacturers began to market generic metandienone in the U.S.

Following further FDA pressure, CIBA withdrew Dianabol from the U.S. market in 1983.<ref name="Llewellyn2011" /> Generic production shut down two years later, when the FDA revoked metandienone's approval entirely in 1985.<ref name="Llewellyn2011" /><ref name="Llewellyn_2011" /><ref>{{cite book | url = https://books.google.com/books?id=lOrf_dHX-RgC&q=1980s+dianabol+ciba&pg=PA232 | title = Muscle, Smoke and Mirrors| vauthors = Roach R | date=2017-01-14 | publisher = AuthorHouse | isbn = 978-1-4670-3840-9}}</ref> Non-medical use was outlawed in the U.S. under the Anabolic Steroids Control Act of 1990.<ref>{{cite web | url = https://www.deadiversion.usdoj.gov/fed_regs/rules/2005/fr1216.htm | title = Implementation of the Anabolic Steroid Control Act of 2004 | author = Diversion Control Division | publisher = United States Department of Justice | access-date = 2017-01-14 | archive-date = 2017-01-16 | archive-url = https://web.archive.org/web/20170116210028/https://www.deadiversion.usdoj.gov/fed_regs/rules/2005/fr1216.htm | url-status = dead }}</ref> While metandienone is controlled and no longer medically available in the U.S., it continues to be produced and used medically in some other countries.<ref name="Llewellyn2011" />

==Society and culture== [[File:Sept-Steroid-Tablets.jpg|thumb|right|250px|Metandienone confiscated by the Drug Enforcement Administration (DEA) in 2008.]]

===Generic names=== ''Metandienone'' is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, while ''methandienone'' is its {{abbrlink|BAN|British Approved Name}} and ''métandiénone'' is its {{abbrlink|DCF|Dénomination Commune Française}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /> It is also referred to as ''methandrostenolone'' and as ''dehydromethyltestosterone''.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Llewellyn2011" /><ref name="Drugs.com" /> The former synonym should not be confused with ''methylandrostenolone'', which is another name for a different AAS known as metenolone.<ref name="IndexNominum2000" />

===Brand names=== Metandienone was introduced and formerly sold primarily under the brand name Dianabol.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /><ref name="Llewellyn2011" /> It has also been marketed under a variety of other brand names including Anabol, Averbol, Chinlipan, Danabol, Dronabol, Metanabol, Methandon, Naposim, Reforvit-B, and Vetanabol among others.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /><ref name="Llewellyn2011" />

===Legal status=== Metandienone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.<ref name="FFFLM2006">{{cite book | vauthors = Karch SB | title = Drug Abuse Handbook | edition = Second | url = https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30 | date=21 December 2006 | publisher = CRC Press | isbn = 978-1-4200-0346-8 | pages = 30– }}</ref>

===Doping in sports=== {{See also|List of doping cases in sport by substance#Metandienone}}

There are many known cases of doping in sports with metandienone by professional athletes.

==References== {{Reflist}}

== External links == {{Other dermatological preparations}} {{Androgens and antiandrogens}} {{Androgen receptor modulators}} {{Estrogen receptor modulators}}

Category:Tertiary alcohols Category:Androgens Category:Androstanes Category:Doping in sport Category:Hepatotoxins Category:Enones Category:Synthetic estrogens Category:Veterinary drugs