Methylepitiostanol, known by the nicknames Epistane, Hemapolin, Havoc, and Epi Plex, is a synthetic and orally active anabolic–androgenic steroid (AAS) of the

dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production o ...

(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, an AAS and antiestrogen which was formerly used in the treatment of

breast cancer Breast cancer is a cancer that develops from breast tissue. Signs of breast cancer may include a Breast lump, lump in the breast, a change in breast shape, dimpling of the skin, Milk-rejection sign, milk rejection, fluid coming from the nipp ...

Japan Japan is an island country in East Asia. Located in the Pacific Ocean off the northeast coast of the Asia, Asian mainland, it is bordered on the west by the Sea of Japan and extends from the Sea of Okhotsk in the north to the East China Sea ...

. Similarly to mepitiostane, 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 (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdr ...

. Methylepitiostanol surfaced on the internet as a novel designer steroid in

dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...

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 the United States 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 synthetic androstane

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

and a 17α-alkylated

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

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

References

{{Estrogen receptor modulators Anabolic–androgenic steroids Androstanes Antineoplastic drugs Antiestrogens Hepatotoxins Episulfides