Methandrostenolone

Methandrostenolone

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Clinical data
Pregnancy category	US: X (Contraindicated)
Routes of administration	Oral
ATC code	A14AA03 (WHO)
Legal status
Legal status	DEA Schedule III (US)
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	4.5-6 hours
Excretion	Renal
Identifiers
IUPAC name (8S,9S,10S,13S,14S,17S)-17-hydroxy-10, 13,17-trimethyl-7,8,9,11,12,14,15,16- octahydro-6H-cyclopenta[a]phenanthren-3-one
CAS Number	72-63-9
PubChem CID	6300
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C20H28O2
Molar mass	300.441 g/mol

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Methandrostenolone (trade names Averbol, Dianabol, Danabol), also known as metandienone (INN), methandienone, or informally as dianabol, is an orally-effective anabolic steroid originally developed in Germany and released in the US in the early 1960s by Ciba Specialty Chemicals. Methandrostenolone is a controlled substance in the United States and Western Europe and remains popular among bodybuilders. An injectable form is sold online from United States based companies. Methandrostenolone is readily available without a prescription in countries such as Mexico (under the trade name Reforvit-b), and is also being manufactured in Asia and many East European countries.

Biophysiology

Methandrostenolone binds tightly to the androgen receptor in order to exert its effects. These include dramatic increases in protein synthesis, glycogenolysis, and muscle strength over a short space of time.Template:Medcn Side effects such as gynecomastia, high blood pressure, acne and male pattern baldness may begin to occur. The drug causes severe masculinising effects in women even at low doses. In addition, it is metabolized into methylestradiol by aromatase. This means that without the administration of aromatase inhibitors such as anastrozole or aminoglutethimide, estrogenic effects will appear over time in men. Many users will combat the estrogenic side effects with Arimidex, Nolvadex or Clomid. In addition, as with other 17α-alkylated steroids, the use of methandrostenolone over extended periods of time can result in liver damage without appropriate care.

The 17α-methylation of the steroid does allow it to pass through the liver with only a small portion of it broken down (hence causing the aforementioned damage to the liver) allowing it to be effective when taken orally. It also has the effect of decreasing the steroid's affinity for sex hormone binding globulin, a protein that de-activates steroid molecules and prevents them from further reactions with the body. As a result, methandrostenolone is significantly more active than an equivalent quantity of testosterone, resulting in rapid growth of muscle tissue. However, the concomitant elevation in estrogen levels - a result of the aromatization of methandrostenolone - results in significant water retention. This gives the appearance of bad gains in mass and strength, which prove to be temporary once the steroid is discontinued and water weight drops. Because of this, it is often used by bodybuilders only at the start of a "steroid cycle", to facilitate rapid strength increases and the appearance of great size, while compounds such as testosterone cypionate or testosterone enanthate with long acting esters build up in the body to an appreciable amount capable of supporting anabolic function on their own.

Usage

As a tonic

In the early 1960s, doctors commonly prescribed 3 tablets per day for women as a tonic. This use was quickly discontinued upon discovery of the heavily masculinising effects of methandrostenolone.

Bodybuilding

Despite the lack of any known therapeutic applications, the drug remained legal until 2001. The United States Congress added certain kinds of steroids which may or may not include methandrostenolone to the Controlled Substances Act as an amendment known as the Anabolic Steroid Control Act of 1990. This act placed steroids in the same category as some amphetamines as a "Schedule III" drug and possession of these drugs results in a felony. It is used by bodybuilders and methandrostenolone continues to be used illegally to this day, typically being combined (stacked) with injectable compounds, such as testosterone propionate, enanthate, cypionate as well as other injectable drugs like trenbolone acetate.

Several successful athletes and professional bodybuilders have come forward and admitted long-term methandrostenolone use before the drug was banned, including Arnold Schwarzenegger. Other steroids stacked with methandrostenolone are primarily, if not always, injectable compounds such as testosterone, trenbolone and nandrolone. Large doses and long-term use of methandrostenolone have been associated with eccentric left ventricular hypertrophy which presents substantially increased risks of cardiomyopathy if and when the hypertrophy atrophies.Template:Medcn Athleticism is typically associated with left-ventricular hypertrophy however natural athleticism generally presents concentric left ventricular growth which is not linked to an increased risk of cardiomyopathy.Template:Medcn

Detection of use

Methandrostenolone 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. Several of the metabolites are unique to methandrostenolone. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry.

History

See also: Weightlifting at the 1960 Summer Olympics

For a period of time John Bosley Ziegler worked at the Ciba Pharmaceutical company, who supplied testosterone for experimental purposes. In the early 1950s his patients included people suffering from burns, as well as the seriously injured or handicapped. In 1954 he administered testosterone, for a period of less than 6 weeks, to several high-level competitive bodybuilders on an experimental basis, but had disappointing results. Dissatisfied and possibly overburdened with patients, he distanced himself from research into performance-enhancing drugs until May 1960, or possibly as early as 1959 (conflicting testimonials).

By the time of the 1960 European Championships in Milan he was understandably suspicious of the Russians - "the Russians are giving their athletes something." Therefore, he asked John Grimek to propose to his chief, Bob Hoffman that steroids be administered to members of the American Olympic team. Mr. Hoffman, however, was cautious and later remarked it was "too close to give to the men who will represent the USA". According to Grimek, "Apparently, he doesn’t think it will do that much good, and may even have detrimental effects , . . .He appears doubtful." Instead, Dianabol was given to two lower level lifters to investigate its effectiveness and safety. After that, Hoffmann retracted his decision and Dianabol was administered to certain Weightlifters on the team.

Synthesis

Treatment of methyltestosterone with selenium dioxide, removes hydrogen from ring A to form a new double bond at C1, yielding methandrostenolone.

Other references

• Wilder EM (October 1962). "Death due to Liver Failure Following the Use of Methandrostenolone". Can Med Assoc J. 87 (14): 768–9. PMC 1849648. PMID 14000685.
• Foss GL (April 1960). "Some Experiences with a New Anabolic Steroid (Methandrostenolone)". Br Med J. 1 (5182): 1300–5. doi:10.1136/bmj.1.5182.1300. PMC 1967563. PMID 13824087.
• Zingg W (October 1965). "The Effect of Methandrostenolone on Nitrogen Excretion Following Open-Heart Surgery". Can Med Assoc J. 93 (15): 816–7. PMC 1928923. PMID 5318132.