Metandienone

Last updated
Metandienone
Metandienone.svg
Clinical data
Trade names Dianabol, 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 class Androgen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability High
Metabolism Hepatic
Elimination half-life 3–6 hours [1] [3]
Excretion Urine
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.716 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H28O2
Molar mass 300.442 g·mol−1
3D model (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 Yes check.svgY
  • Key:XWALNWXLMVGSFR-HLXURNFRSA-N Yes check.svgY
   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 still quite often used because of its affordability and effectiveness for bulking cycles. [4] [5] [1] [6] It is also used non-medically for physique- and performance-enhancing purposes. [1] It is often taken by mouth. [1]

Contents

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]

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
RouteMedicationMajor brand namesFormDosage
Oral Testosterone a–Tablet400–800 mg/day (in divided doses)
Testosterone undecanoate Andriol, JatenzoCapsule40–80 mg/2–4x day (with meals)
Methyltestosterone bAndroid, Metandren, TestredTablet10–50 mg/day
Fluoxymesterone bHalotestin, Ora-Testryl, UltandrenTablet5–20 mg/day
MetandienonebDianabolTablet5–15 mg/day
Mesterolone bProvironTablet25–150 mg/day
Sublingual Testosterone bTestoralTablet5–10 mg 1–4x/day
Methyltestosterone bMetandren, Oreton MethylTablet10–30 mg/day
Buccal Testosterone StriantTablet30 mg 2x/day
Methyltestosterone bMetandren, Oreton MethylTablet5–25 mg/day
Transdermal Testosterone AndroGel, Testim, TestoGelGel25–125 mg/day
Androderm, AndroPatch, TestoPatchNon-scrotal patch2.5–15 mg/day
TestodermScrotal patch4–6 mg/day
AxironAxillary solution30–120 mg/day
Androstanolone (DHT) AndractimGel100–250 mg/day
Rectal Testosterone Rektandron, TestosteronbSuppository40 mg 2–3x/day
Injection (IM Tooltip intramuscular injection or SC Tooltip subcutaneous injection) Testosterone Andronaq, Sterotate, VirosteroneAqueous suspension10–50 mg 2–3x/week
Testosterone propionate bTestovironOil solution10–50 mg 2–3x/week
Testosterone enanthate DelatestrylOil solution50–250 mg 1x/1–4 weeks
XyostedAuto-injector50–100 mg 1x/week
Testosterone cypionate Depo-TestosteroneOil solution50–250 mg 1x/1–4 weeks
Testosterone isobutyrate Agovirin DepotAqueous suspension50–100 mg 1x/1–2 weeks
Testosterone phenylacetate bPerandren, AndrojectOil solution50–200 mg 1x/3–5 weeks
Mixed testosterone esters Sustanon 100, Sustanon 250Oil solution50–250 mg 1x/2–4 weeks
Testosterone undecanoate Aveed, NebidoOil solution750–1,000 mg 1x/10–14 weeks
Testosterone buciclate a–Aqueous suspension600–1,000 mg 1x/12–20 weeks
Implant Testosterone TestopelPellet150–1,200 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 physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters. [1] It is said to be the most widely used AAS for such purposes both today and historically. [1]

Side effects

Androgenic side effects such as oily skin, acne, seborrhea, increased facial/body hair growth, scalp hair loss, and virilization may occur. [1] Estrogenic side effects such as gynecomastia and 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
MedicationRatioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone1:1–1:8
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 androgen receptor (AR) in order to exert its effects. [23] These include dramatic increases in protein synthesis, glycogenolysis, and muscle strength over a short space of time.[ medical citation needed ] While it can be metabolized by 5α-reductase into methyl-1-testosterone (17α-methyl-δ1-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. [1] [24] As such, 5α-reductase inhibitors like finasteride and dutasteride do not reduce the androgenic effects of metandienone. [1] 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. [1] As such, it is only really commonly used in men. [1]

Metandienone is a substrate for aromatase and can be metabolized into the estrogen methylestradiol (17α-methylestradiol). [25] 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. [25] As such, it can cause side effects such as gynecomastia and fluid retention. [25] 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. [25] Metandienone has no progestogenic activity. [25]

As with other 17α-alkylated AAS, metandienone may be hepatotoxic, especially with prolonged use of high doses. [1]

Pharmacokinetics

Metandienone has high oral bioavailability. [1] 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. [26] The drug is metabolized in the liver by 6β-hydroxylation, 3α- and 3β-oxidation, 5β-reduction, 17-epimerization, and conjugation among other reactions. [24] Unlike methyltestosterone, owing to the presence of its C1(2) double bond, metandienone does not produce 5α-reduced metabolites. [24] [1] [27] The elimination half-life of metandienone is about 3 to 6 hours. [1] [3] It is eliminated in the urine. [24]

Chemistry

Metandienone, also known as 17α-methyl-δ1-testosterone or as 17α-methylandrost-1,4-dien-17β-ol-3-one, is a synthetic androstane steroid and a 17α-alkylated derivative of testosterone. [7] 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. [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. [28] Several of the metabolites are unique to metandienone. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry. [29] [30]

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, [31] and began marketing the drug as Dianabol in 1958 in the U.S. [1] [32] 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. [33] Early adopters included players for Oklahoma University and San Diego Chargers head coach Sid Gillman, who administered Dianabol to his team starting in 1963. [34]

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. [35] 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. [36] 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. [1] Generic production shut down two years later, when the FDA revoked metandienone's approval entirely in 1985. [1] [36] [37] Non-medical use was outlawed in the U.S. under the Anabolic Steroids Control Act of 1990. [38] 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. Sept-Steroid-Tablets.jpg
Metandienone confiscated by the Drug Enforcement Administration (DEA) in 2008.

Generic names

Metandienone is the generic name of the drug and its INN Tooltip International Nonproprietary Name, while methandienone is its BAN Tooltip British Approved Name and métandiénone is its DCF Tooltip 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]

Metandienone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act. [39]

Doping in sports

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

Related Research Articles

<span class="mw-page-title-main">Methyltestosterone</span> Chemical compound

Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. It is taken by mouth or held in the cheek or under the tongue.

<span class="mw-page-title-main">Metenolone</span> Chemical compound

Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate and metenolone enanthate. Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure. Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.

<span class="mw-page-title-main">Oxandrolone</span> Androgen and anabolic steroid

Oxandrolone, sold under the brand names Oxandrin and Anavar, among others, is an androgen and anabolic steroid (AAS) medication which is used to help promote weight gain in various situations, to help offset protein catabolism caused by long-term corticosteroid therapy, to support recovery from severe burns, to treat bone pain associated with osteoporosis, to aid in the development of girls with Turner syndrome, and for other indications. It is taken by mouth.

<span class="mw-page-title-main">Oxymetholone</span> Androgen and anabolic steroid

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemia. It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain and muscle growth in certain situations. It is taken by mouth.

<span class="mw-page-title-main">Quinbolone</span> Chemical compound

Quinbolone, sold under the brand names Anabolicum and Anabolvis, is an androgen and anabolic steroid (AAS) which was previously marketed in Italy. It was developed by Parke-Davis as a viable orally administered AAS with little or no liver toxicity.

<span class="mw-page-title-main">Metenolone enanthate</span> Chemical compound

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.

<span class="mw-page-title-main">Mesterolone</span> Chemical compound

Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. It has also been used to treat male infertility, although this use is controversial. It is taken by mouth.

<span class="mw-page-title-main">Fluoxymesterone</span> Chemical compound

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth.

<span class="mw-page-title-main">Mestanolone</span> Chemical compound

Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer used. It is still available for use in Japan however. It is taken by mouth.

<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor. Anabolic steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance.

<span class="mw-page-title-main">Enestebol</span> Chemical compound

Enestebol, also known as 4-hydroxy-17α-methyl-δ1-testosterone, as well as 4,17β-dihydroxy-17α-methylandrosta-1,4-dien-3-one, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of testosterone which was never marketed. It is closely related to oxymesterone (4-hydroxy-17α-methyltestosterone), as well as to chlorodehydromethyltestosterone (4-chloro-17α-methyl-δ1-testosterone), methylclostebol (4-chloro-17α-methyltestosterone), and metandienone (17α-methyl-δ1-testosterone).

<span class="mw-page-title-main">Normethandrone</span> Chemical compound

Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.

<span class="mw-page-title-main">Methylestradiol</span> Chemical compound

Methylestradiol, sold under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, is an estrogen medication which is used in the treatment of menopausal symptoms. It is formulated in combination with normethandrone, a progestin and androgen/anabolic steroid medication. Methylestradiol is taken by mouth.

<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.

<span class="mw-page-title-main">Boldenone undecylenate</span> Chemical compound

Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used in humans as well. It is given by injection into muscle.

<span class="mw-page-title-main">Methylhydroxynandrolone</span> Chemical compound

Methylhydroxynandrolone, also known as 4-hydroxy-17α-methyl-19-nortestosterone (HMNT), as well as 4,17β-dihydroxy-17α-methylestr-4-en-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of nandrolone (19-nortestosterone) which was never marketed. It was first described in 1964 and was studied in the treatment of breast cancer, but was not introduced for clinical use. The drug re-emerged in 2004 when it started being sold on the Internet as a "dietary supplement". MOHN joined other AAS as a controlled substance in the United States on 20 January 2005.

<span class="mw-page-title-main">11β-Methyl-19-nortestosterone</span> Chemical compound

11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

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