Metandienone

Metandienone
Clinical data
Trade names	Dianabol, others
Other names	Methandienone; Methandrostenolone; Methandrolone; Dehydromethyltestosterone; Methylboldenone; Perabol; Ciba-17309-Ba; TMV-17; NSC-51180; NSC-42722; 17α-Methyl-δ1-testosterone; 17β-Hydroxy-17α-methylandrosta-1,4-dien-3-one; 17α-Methylandrost-1,4-dien-17β-ol-3-one
Routes of; administration	By mouth, intramuscular injection (veterinary)
Drug class	Androgen; Anabolic steroid
ATC code	A14AA03 (WHO) D11AE01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C5 (Anabolic steroids); CA: Schedule IV; US: Schedule III;
Pharmacokinetic data
Bioavailability	High
Metabolism	Hepatic
Elimination half-life	3–6 hours
Excretion	Urine
Identifiers
CAS Number	72-63-9 ;
PubChem CID	6300;
DrugBank	DB13586 ;
ChemSpider	6061 ;
UNII	COZ1R7EOCC;
KEGG	D00389;
ChEMBL	ChEMBL1418176 ;
CompTox Dashboard (EPA)	DTXSID2023276 ;
ECHA InfoCard	100.000.716
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=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 ; Key:XWALNWXLMVGSFR-HLXURNFRSA-N ;
	S,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[aphenanthren-3-one&page2=Metandienone (verify)]

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.^[4]^[5]^[1]^[6] It is also used non-medically for physique- and performance-enhancing purposes.^[1] It is often taken by mouth.^[1]

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.^[1] 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.^[1] It also has moderate estrogenic effects.^[1]

Metandienone was originally developed in 1955 by CIBA and marketed in Germany and the United States.^[1]^[7]^[4]^[8]^[9] 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.^[10]^[8]^[11]^[12] It is currently a controlled substance in the United States^[13] and United Kingdom^[14] 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.^[6]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 444–454, 533. ISBN 978-0-9828280-1-4.
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ Ruiz P, Strain EC (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5.
^ ^a ^b Swiss Pharmaceutical Society (2000). "Metandienone". Index Nominum 2000: International Drug Directory. Taylor & Francis. p. 660. ISBN 978-3-88763-075-1.
^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.
^ ^a ^b "Metandienone". drugs.com.
^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 781–. ISBN 978-1-4757-2085-3.
^ ^a ^b Yesalis CE, Anderson WA, Buckley WE, Wright JE (1990). "Incidence of the nonmedical use of anabolic-androgenic steroids" (PDF). NIDA Research Monograph. 102: 97–112. PMID 2079979. Archived from the original (PDF) on 2007-10-31. Retrieved 2007-09-26.
^ Fair JD (1993). "Isometrics or Steroids? Exploring New Frontiers Of Strength in the Early 1960s" (PDF). Journal of Sport History. 20 (1): 1–24. Archived from the original (PDF) on 2008-05-28.
^ Yesalis C, Bahrke M (2002). "History of Doping in Sport" (PDF). International Sports Studies. 24: 42–76. Archived from the original (PDF) on 2017-11-23. Retrieved 2017-01-14.
^ Lin GC, Erinoff L (1996-07-01). Anabolic Steroid Abuse. DIANE Publishing. p. 29. ISBN 978-0-7881-2969-8. dianabol history.
^ Helms E (August 2014). "What can be achieved as a natural bodybuilder?" (PDF). Alan Aragon's Research Review. Alan Aragon.
^ Controlled Substances, Alphabetical Order (PDF). United States Drug Enforcement Administration. Archived from the original (PDF) on 2016-04-17. Retrieved 2013-04-06.
^ "List of most commonly encountered drugs currently controlled under the misuse of drugs legislation". www.gov.uk. Retrieved 2017-01-14.

[Llewellyn2011-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 444–454, 533. ISBN 978-0-9828280-1-4.

[2] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[RuizStrain2011-3] Ruiz P, Strain EC (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5.

[IndexNominum2000-4] Swiss Pharmaceutical Society (2000). "Metandienone". Index Nominum 2000: International Drug Directory. Taylor & Francis. p. 660. ISBN 978-3-88763-075-1.

[MortonHall2012-5] Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.

[Drugs.com-6] "Metandienone". drugs.com.

[Elks2014-7] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 781–. ISBN 978-1-4757-2085-3.

[Yesali_1990-8] Yesalis CE, Anderson WA, Buckley WE, Wright JE (1990). "Incidence of the nonmedical use of anabolic-androgenic steroids" (PDF). NIDA Research Monograph. 102: 97–112. PMID 2079979. Archived from the original (PDF) on 2007-10-31. Retrieved 2007-09-26.

[Fair_1993-9] Fair JD (1993). "Isometrics or Steroids? Exploring New Frontiers Of Strength in the Early 1960s" (PDF). Journal of Sport History. 20 (1): 1–24. Archived from the original (PDF) on 2008-05-28.

[Yesalis_2002-10] Yesalis C, Bahrke M (2002). "History of Doping in Sport" (PDF). International Sports Studies. 24: 42–76. Archived from the original (PDF) on 2017-11-23. Retrieved 2017-01-14.

[11] Lin GC, Erinoff L (1996-07-01). Anabolic Steroid Abuse. DIANE Publishing. p. 29. ISBN 978-0-7881-2969-8. dianabol history.

[12] Helms E (August 2014). "What can be achieved as a natural bodybuilder?" (PDF). Alan Aragon's Research Review. Alan Aragon.

[13] Controlled Substances, Alphabetical Order (PDF). United States Drug Enforcement Administration. Archived from the original (PDF) on 2016-04-17. Retrieved 2013-04-06.

[14] "List of most commonly encountered drugs currently controlled under the misuse of drugs legislation". www.gov.uk. Retrieved 2017-01-14.

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