Methandrostenolone
| |
| Methandrostenolone
| |
| 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 | |
| Identifiers | |
| CAS number | |
| ATC code | A14 |
| PubChem | |
| Chemical data | |
| Formula | C20H28O2 |
| Mol. mass | 300.441 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | Hepatic |
| Half life | 4.5-6 hours |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. |
X(US) |
| Legal status | |
| Routes | Oral |
Methandrostenolone (Dianabol) is an anabolic steroid originally developed by John Ziegler and released in the US in 1958 by Ciba.[1][2] It was used as an aid to muscle growth by bodybuilders until its ban by the FDA under the Controlled Substances Act.
Methandrostenolone does not react strongly with the androgen receptor[3], instead relying on activity not mediated by the receptor for its effects. These include dramatic increases in protein synthesis, glycogenolysis, and muscle strength over a short space of time. However, due to its mode of action, it decreases the rate of cell respiration and decreases production of red blood cells. In high doses (30 mg or more per day), side effects such as gynaecomastia, 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 estradiol 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 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.
In the early 1960s, doctors commonly prescribed a tablet per day for women as a tonic. This use was quickly discontinued upon discovery of the heavily masculinising effects of methandrostenolone. However, despite the lack of any known therapeutic applications, the drug remained legal until the early 1990s.
The 17α-methylation of the steroid does allow it to pass through the liver without being broken down (hence causing the aforementioned damage to the liver) allowing it to be 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 great 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 or nandrolone with long acting esters build up in the body to an appreciable amount capable of supporting anabolic function on their own.
References
- Death due to Liver Failure Following the Use of Methandrostenolone Edmund M. Wilder, Can Med Assoc J. 1962 October 6; 87(14): 768–769.
- Some Experiences with a New Anabolic Steroid (Methandrostenolone) George L. Foss, Br Med J. 1960 April 30; 1(5182): 1300–1305.
- The Effect of Methandrostenolone on Nitrogen Excretion Following Open-Heart Surgery Walter Zingg, Can Med Assoc J, Oct.9, 1965, vol 93
Anabolic steroids (A14) (trademark names in brackets) | |
|---|---|
| Androstan (carbon 19 present) | Androstadienone • Boldenone undecylenate (Equipoise) • 4-Chlordehydromethyltestosterone (Turinabol) • Clostebol • Desoxymethyltestosterone (Madol) • DHEA • DHT • Drostanolone (Masteron) • Fluoxymesterone (Halotestin) • Furazabol (Miotolan) • Methandrostenolone (Dianabol) • Methenolone • Mesterolone (Proviron) • Methenolone enanthate (Primobolan) • Mestanolone • Norethandrolone • Oxandrolone (Anavar) • Oxymetholone (Anadrol) • Oxymetholone (Anadrol-50) • Quinbolone (Anabolicum Vister) • Stanozolol (Winstrol) • Testosterone |
| Estren (carbon 19 absent) | Ethylestrenol • Mibolerone (Cheque Drops) • Nandrolone (Deca Durabolin) • Norbolethone (Genabol) • Oxabolone cipionate • Tetrahydrogestrinone (The Clear) • Trenbolone (Fina) |
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