Metandienone

Source: Wikipedia, the free encyclopedia.
Metandienone
Clinical data
Trade namesDianabol, others
Other namesMethandienone; 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)[1]
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
JSmol)
  • 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=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 checkY
  • Key:XWALNWXLMVGSFR-HLXURNFRSA-N checkY
  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

physique- and performance-enhancing purposes.[1] It is often taken by mouth.[1]

anabolic effects and moderate androgenic effects.[1] It also has moderate estrogenic effects.[1]

Metandienone was originally developed in 1955 by

bodybuilders. Metandienone is readily available without a prescription in certain countries such as Mexico, and is also manufactured in some Asian countries.[6]

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as a form of androgen replacement therapy for the treatment of hypogonadism in men, but has since been discontinued and withdrawn in most countries, including in the United States.[15][4][6]

It was given at a dosage of 5 to 10 mg/day in men and 2.5 mg/day in women.[16][17][1]

Androgen replacement therapy formulations and dosages used in men
Route Medication Major brand names Form Dosage
Oral Testosteronea – Tablet 400–800 mg/day (in divided doses)
Testosterone undecanoate Andriol, Jatenzo Capsule 40–80 mg/2–4x day (with meals)
Methyltestosteroneb Android, Metandren, Testred Tablet 10–50 mg/day
Fluoxymesteroneb Halotestin, Ora-Testryl, Ultandren Tablet 5–20 mg/day
Metandienoneb Dianabol Tablet 5–15 mg/day
Mesteroloneb Proviron Tablet 25–150 mg/day
Sublingual Testosteroneb Testoral Tablet 5–10 mg 1–4x/day
Methyltestosteroneb Metandren, Oreton Methyl Tablet 10–30 mg/day
Buccal Testosterone Striant Tablet 30 mg 2x/day
Methyltestosteroneb Metandren, Oreton Methyl Tablet 5–25 mg/day
Transdermal
 Testosterone AndroGel, Testim, TestoGel Gel 25–125 mg/day
Androderm, AndroPatch, TestoPatch Non-scrotal patch 2.5–15 mg/day
Testoderm Scrotal patch 4–6 mg/day
Axiron Axillary solution 30–120 mg/day
Androstanolone (DHT) Andractim Gel 100–250 mg/day
Rectal Testosterone Rektandron, Testosteronb Suppository 40 mg 2–3x/day
SC
Tooltip subcutaneous injection)		 Testosterone Andronaq, Sterotate, Virosterone Aqueous suspension 10–50 mg 2–3x/week
Testosterone propionateb Testoviron Oil solution 10–50 mg 2–3x/week
Testosterone enanthate Delatestryl Oil solution 50–250 mg 1x/1–4 weeks
Xyosted Auto-injector 50–100 mg 1x/week
Testosterone cypionate Depo-Testosterone Oil solution 50–250 mg 1x/1–4 weeks
Testosterone isobutyrate Agovirin Depot Aqueous suspension 50–100 mg 1x/1–2 weeks
Testosterone phenylacetateb Perandren, Androject Oil solution 50–200 mg 1x/3–5 weeks
Mixed testosterone esters Sustanon 100, Sustanon 250 Oil solution 50–250 mg 1x/2–4 weeks
Testosterone undecanoate Aveed, Nebido Oil solution 750–1,000 mg 1x/10–14 weeks
Testosterone buciclatea – Aqueous suspension 600–1,000 mg 1x/12–20 weeks
Implant Testosterone Testopel Pellet 150–1,200 mg/3–6 months
Notes: Men produce about 3 to 11 mg testosterone per day (mean 7 mg/day in young men). Footnotes: a = Never marketed. b = No longer used and/or no longer marketed. Sources: See template.

Available forms

Metandienone was provided in the form of 2.5, 5 mg and 10mg oral tablets.[18][19][20][1]

Non-medical uses

Metandienone is used for

powerlifters.[1] It is said to be the most widely used AAS for such purposes both today and historically.[1]

Side effects

See also: Anabolic steroid § Adverse effects

fluid retention can also occur.[1] Case reports of gynecomastia exist.[21][22] 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.[1]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

Methandienone binds to and activates the

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.[1] As such, it is only really commonly used in men.[1]

Metandienone is a

fluid retention.[1] 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.[1] Metandienone has no progestogenic activity.[1]

As with other 17α-alkylated AAS, metandienone may be

hepatotoxic, especially with prolonged use of high doses.[1]

Pharmacokinetics

Metandienone has high

elimination half-life of metandienone is about 3 to 6 hours.[1][3] It is eliminated in the urine.[24]

Chemistry

See also:
List of androgens/anabolic steroids

Metandienone, also known as 17α-methyl-δ1-testosterone or as 17α-methylandrost-1,4-dien-17β-ol-3-one, is a

modification of testosterone with a methyl group at the C17α position and an additional double bond between the C1 and C2 positions.[7] The drug is also the 17α-methylated derivative of boldenone (δ1-testosterone) and the δ1 analogue of methyltestosterone (17α-methyltestosterone).[7]

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 mg oral dose.[27] Several of the metabolites are unique to metandienone. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry.[28][29]

History

Metandienone was first described in 1955.[1] It was synthesized by researchers at the CIBA laboratories in Basel, Switzerland. CIBA filed for a U.S. patent in 1957,[30] and began marketing the drug as Dianabol in 1958 in the U.S.[1][31] 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.[32] Early adopters included players for Oklahoma University and San Diego Chargers head coach Sid Gillman, who administered Dianabol to his team starting in 1963.[33]

After the

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.

Anabolic Steroids Control Act of 1990.[37] 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.[1]

Society and culture

Metandienone confiscated by the Drug Enforcement Administration (DEA) in 2008.

Generic names

Metandienone is the

INNTooltip International Nonproprietary Name, while methandienone is its BANTooltip British Approved Name and métandiénone is its DCFTooltip Dénomination Commune Française.[7][4][5][6] It is also referred to as methandrostenolone and as dehydromethyltestosterone.[7][4][5][1][6] The former synonym should not be confused with methylandrostenolone, which is another name for a different AAS known as metenolone.[4]

Brand names

Metandienone was introduced and formerly sold primarily under the brand name Dianabol.[7][4][5][6][1] 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.[7][4][5][6][1]

Legal status

Metandienone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[38]

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

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  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.
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  6. ^ a b c d e f g "Metandienone". drugs.com.
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    PMID 2079979. Archived from the original
    (PDF) on 2007-10-31. Retrieved 2007-09-26.
  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.
  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. 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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  17. ^ ABPI Data Sheet Compendium. Pharmind Pub. 1978.
  18. ^ National Drug Code Directory. Consumer Protection and Environmental Health Service, Public Health Service, U.S. Department of Health, Education, and Welfare. 1982. pp. 642–.
  19. ^ Federal Register. Office of the Federal Register, National Archives and Records Service, General Services Administration. 18 January 1983. pp. 2208–2209.
  20. ^ The National Formulary ... American Pharmaceutical Association. 1974. Tablets available — Methandrostenolone Tablets usually available contain the following amounts of methandrostenolone: 2.5 and 5 mg.
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    S2CID 20197705
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  28. ^ Baselt R (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 952–4.
  29. S2CID 10051396
    .
  30. ^ US granted 2900398, Wettstein A, Hunger A, Meystre C, Ehmann L, "Process for the manufacture of steroid dehydrogenation products", issued 18 August 1959, assigned to Ciba Pharmaceutical Products, Inc. 
  31. ^ Chaney M (16 June 2008). "Dianabol, the first widely used steroid, turns 50". NY Daily News. Retrieved 2017-01-14.
  32. ISSN 1091-2339
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  33. ^ Quinn TJ (2009-02-01). "OTL: Football's first steroids team? The '63 Chargers". ESPN. Retrieved 2017-01-14.
  34. S2CID 87333977
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  37. ^ Diversion Control Division. "Implementation of the Anabolic Steroid Control Act of 2004". United States Department of Justice. Archived from the original on 2017-01-16. Retrieved 2017-01-14.
  38. ISBN 978-1-4200-0346-8
    .

External links

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