Methasterone, also known as methyldrostanolone and known by the nickname Superdrol, is a

synthetic Synthetic things are composed of multiple parts, often with the implication that they are artificial. In particular, 'synthetic' may refer to: Science * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic o ...

and

orally active Oral administration is a route of administration where a substance is taken through the mouth. Per os abbreviated to P.O. is sometimes used as a direction for medication to be taken orally. Many medications are taken orally because they are in ...

anabolic–androgenic steroid Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone as well as synthetic androgens that are structurally related and have similar effects t ...

(AAS) which was never marketed for medical use. It was sold legally for 9 years as a body building supplement. Because of this lengthy time being legal it has more studies and references than most other designer steroids.

Medical uses

Methasterone was never a commercially available prescription drug. Its non-17α-alkylated counterpart,

drostanolone propionate Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no long ...

, was commercialized by Syntex Corporation under the brand name Masteron.

Non-medical uses

Methasterone resurfaced in 2005 as a “designer steroid”. It was brought to market by Designer Supplements as the primary ingredient of a

dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...

named Superdrol. Its introduction into commerce may have represented an attempted circumvention of the U.S. Anabolic Steroids Control Act of 1990 (along with its 2004 revision), since the law is, in part, drug-specific; methasterone, as is the case with many designer steroids, was not declared a Schedule III class anabolic steroid in that act because it was not commercially available at the time the act, and its subsequent revision, were signed into law. Methasterone was therefore being sold as an over-the-counter dietary supplement.

Side effects

Methasterone is

hepatotoxic Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn f ...

(toxic to the liver). Several cases of liver damage due to the use of methasterone have been cited in the medical literature.

Chemistry

Methasterone, also known as 2α,17α-dimethyl-5α-dihydrotestosterone (2α,17α-dimethyl-DHT) or as 2α,17α-dimethyl-5α-androstan-17β-ol-3-one, is a

androstane

steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...

and a 17α-alkylated derivative of DHT.

Mebolazine Mebolazine (; brand names Dostalon and Roxilon; also known as dimethazine, dymethazine, di(methasterone) azine, or 2α,17α-dimethyl-5α-androstan-17β-ol-3-one azine) is a synthetic, orally active androgen/anabolic steroid (AAS) and a 17α-alk ...

is formed by hydrazone formation between two equivalents of methasterone with one equivalent of

hydrazine Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazine ...

History

The synthesis of methasterone is first mentioned in the literature in 1956 in connection with research conducted by Syntex Corporation in order to discover a compound with anti-tumor properties. In a 1959 research journal article, it is initially mentioned and is elaborated upon where its method of synthesis is discussed in greater detail, its tumor inhibiting properties are verified, and it is noted as being a “potent orally active anabolic agent exhibiting only weak androgenic activity.” The results of subsequent assays to determine methasterone's anabolic and androgenic activity were published in Vida's Androgens and Anabolic Agents, a dated but still standard reference, where it was noted that methasterone possessed the oral bioavailability of methyltestosterone while being 400% as anabolic and 20% as androgenic, yielding a Q-ratio (anabolic to androgenic ratio) of 20, which is considered very high.

Designer steroid

It was in late 2005 that the reclassification of methasterone as AAS (as well as that of four other designer steroids) was brought to public awareness via an article published in the ''Washington Post''. Don Catlin of the UCLA Olympic Laboratory, who conducted the studies, noted methasterone's similarity to drostanolone. A warning by the FDA was issued soon after to the general public as well as to the distributor, Designer Supplements LLC, for the marketing of this compound. Methasterone was subsequently added to the World Anti-Doping Agency (WADA) list of prohibited substances in sport. Despite all of this, methasterone has resurfaced within the supplement industry on several occasions since its banning by WADA.

References

{{Androgen receptor modulators Abandoned drugs Androgens and anabolic steroids Androstanes Designer drugs Hepatotoxins World Anti-Doping Agency prohibited substances