Methandrostenolone

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Methandrostenolone
Metandienone.svg
Systematic (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
Clinical data
Pregnancy cat.
Legal status
Routes Oral
Pharmacokinetic data
Bioavailability Oral
Metabolism Hepatic
Half-life 4.5-6 hours
Excretion Renal
Identifiers
CAS number 72-63-9 YesY
ATC code A14AA03 D11AE01
PubChem CID 6300
ChemSpider 6061 YesY
UNII COZ1R7EOCC YesY
ChEMBL CHEMBL1418176 N
Chemical data
Formula C20H28O2 
Mol. mass 300.441 g/mol
 N (what is this?)  (verify)

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.[1][2] Methandrostenolone is a controlled substance in the United States[3] 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[edit]

Methandrostenolone binds tightly to the androgen receptor in order to exert its effects.[4] These include dramatic increases in protein synthesis, glycogenolysis, and muscle strength over a short space of time.[medical citation needed] 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[edit]

As a tonic[edit]

17α-methandrostenolone confiscated by the DEA in 2008.
Methandrostenolone pills.

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[edit]

Despite the lack of any known therapeutic applications, the drug remained legal until 2001.[citation needed] The United States Congress added certain kinds of steroids which may or may not include methandrostenolone [clarification needed] to the Controlled Substances Act as an amendment known as the Anabolic Steroid Control Act of 1990.[citation needed] 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.[citation needed]

Several successful athletes and professional bodybuilders have come forward and admitted long-term methandrostenolone use before the drug was banned, including Arnold Schwarzenegger.[5][dead link][6][dead link] Other steroids stacked with methandrostenolone are primarily, if not always, injectable compounds such as testosterone, trenbolone and nandrolone.[citation needed] Large doses and long-term use of methandienone have been associated with eccentric left-ventricular hypertrophy which presents substantially increased risks of cardiomyopathy if and when the hypertrophy atrophies.[medical citation needed] 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.[medical citation needed]

Detection of use[edit]

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.[7] Several of the metabolites are unique to methandrostenolone. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry.[8][9]

History[edit]

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).[citation needed]

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.[citation needed][10][11]

Synthesis[edit]

Methandrostenolone synthesis:[12]

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

Footnotes[edit]

  1. ^ Yesalis CE, Anderson WA, Buckley WE, Wright JE (1990). "Incidence of the nonmedical use of anabolic-androgenic steroids". NIDA Res. Monogr. 102: 97–112. PMID 2079979. 
  2. ^ Fair JD (1993). "Isometrics or Steroids? Exploring New Frontiers Of Strength in the Early 1960s". Journal of Sport History 20 (1): 1–24. 
  3. ^ Drug Enforcement Administration. "Controlled Substances, Alphabetical Order". 
  4. ^ Roselli CE (May 1998). "The effect of anabolic-androgenic steroids on aromatase activity and androgen receptor binding in the rat preoptic area". Brain Res. 792 (2): 271–6. doi:10.1016/S0006-8993(98)00148-6. PMID 9593936. 
  5. ^ Steve Theunissen: Arnold & Steroids: Truth Revealed 2002
  6. ^ "Interview with Sergio Oliva". Fitnessprat.no. 2010-10-18. Retrieved 2012-02-13. 
  7. ^ Schänzer W, Geyer H, Fusshöller G, Halatcheva N, Kohler M, Parr MK, Guddat S, Thomas A, Thevis M. Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine. Rapid Commun. Mass Spectrom. 20: 2252-8, 2008.
  8. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 952-954.
  9. ^ Fragkaki AG, Angelis YS, Tsantili-Kakoulidou A, Koupparis M, Georgakopoulos C. Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine. J. Steroid Biochem. Mol. Biol. 115: 44-61, 2009.
  10. ^ "The Ultimate Strength Exercise 1, Bill Starr" (PDF). Retrieved 2012-02-13. 
  11. ^ "The Ultimate Strength Exercise 2, Bill Starr" (PDF). Retrieved 2012-02-13. 
  12. ^ Meystre, Ch. (1956). "Gewinnung von 1;4-Bisdehydro-3-oxo-steroiden. Uber Steroide, 139. Mitteilung". Helvetica Chimica Acta 39 (3): 734–742. doi:10.1002/hlca.19560390314.  edit

Other references[edit]