Methylepitiostanol, known by the nicknames Epistane, Hemapolin, Havoc, and Epi Plex, 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 ...

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) of the

dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues includi ...

(DHT) group which was first described in the literature in 1974 but was never marketed for medical use. It is the 17α-methylated derivative of

epitiostanol Epitiostanol, sold under the brand name Thiodrol, is an injection (medicine), injected antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was described in the literature in 1965 and has been marketed ...

, an AAS and

antiestrogen Antiestrogens, also known as estrogen antagonists or estrogen blockers, are a class of drugs which prevent estrogens like estradiol from mediating their biological effects in the body. They act by blocking the estrogen receptor (ER) and/or ...

which was formerly used in the treatment of

breast cancer Breast cancer is cancer that develops from breast tissue. Signs of breast cancer may include a lump in the breast, a change in breast shape, dimpling of the skin, milk rejection, fluid coming from the nipple, a newly inverted nipple, or ...

Japan Japan ( ja, 日本, or , and formally , ''Nihonkoku'') is an island country in East Asia. It is situated in the northwest Pacific Ocean, and is bordered on the west by the Sea of Japan, while extending from the Sea of Okhotsk in the n ...

. Similarly to

mepitiostane Mepitiostane, sold under the brand name Thioderon, is an oral administration, orally active antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which is marketed in Japan as an antineoplastic agent for the ...

, methylepitiostanol is an orally active variant of epitiostanol. Due to its C17α methyl group, the drug is considered to have a high potential for

hepatotoxicity 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 fr ...

. Methylepitiostanol surfaced on the internet as a novel

designer steroid A designer drug is a structural analog, structural or Functional analog (chemistry), functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as ill ...

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 ...

s around 2009. It was identified in 2015 in over 30 products sold online that listed it as an ingredient on their product label. It became a controlled substance in 2014 with the passage of the Designer Anabolic Steroid Control Act, being one of the 27 new steroids explicitly listed as controlled by the Act.

Chemistry

Methylepitiostanol, also known as 2α,3α-epithio-17α-methyl-4,5α-dihydrotestosterone (2α,3α-epithio-17α-methyl-DHT) or as 2α,3α-epithio-17α-methyl-5α-androstan-17β-ol, is a

androstane Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane. File:androstane.png, 5α-Androstane File:androstane 5beta.png, 5β-Androstane Pharmacology ...

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 ...

and a 17α-alkylated

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

of DHT. It is closely related to epitiostanol (2α,3α-epithio-DHT) and mepitiostane (epitiostanol 17-methyloxycyclopentyl ether).

References

{{Estrogen receptor modulators Androgens and anabolic steroids Androstanes Antineoplastic drugs Antiestrogens Hepatotoxins Episulfides