Methylepitiostanol

Methylepitiostanol, known by the nicknames Epistane, Hemapolin, Havoc, and Epi Plex, is a synthetic and orally active anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was first described in the literature in 1974 but was never marketed for medical use.^[1][2][3] It is the 17α-methylated derivative of epitiostanol, an AAS and antiestrogen which was formerly used in the treatment of breast cancer in Japan.^[1][2] Similarly to mepitiostane, methylepitiostanol is an orally active variant of epitiostanol.^[1][2] Due to its C17α methyl group, the drug is considered to have a high potential for hepatotoxicity.^[1]

Methylepitiostanol

Clinical data
Other names	Epistane; Hemapolin; Havoc; Epi Plex; Methylepithiostanol; Methepitiostane; 17α-Methylepitiostanol; 2α,3α-Epithio-17α-methyl-4,5α-dihydrotestosterone; 2α,3α-Epithio-17α-methyl-DHT
Routes of administration	By mouth[1]
Drug class	Androgen; Anabolic steroid; Antiestrogen
ATC code	None
Legal status
Legal status	US: Schedule III
Identifiers
IUPAC name (1S,2S,4R,6S,8S,11R,12S,15S,16S)-2,15,16-Trimethyl-5-thiapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-ol
CAS Number	4267-80-5
PubChem CID	71752521
ChemSpider	48063843
UNII	Z50OE1022B
Chemical and physical data
Formula	C20H32OS
Molar mass	320.54 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC12CCC3C(C1CCC2(C)O)CCC4C3(CC5C(C4)S5)C
InChI InChI=1S/C20H32OS/c1-18-11-17-16(22-17)10-12(18)4-5-13-14(18)6-8-19(2)15(13)7-9-20(19,3)21/h12-17,21H,4-11H2,1-3H3/t12-,13+,14-,15-,16-,17+,18-,19-,20-/m0/s1 Key:UPLPHRJJTCUQAY-WIRWPRASSA-N

Methylepitiostanol surfaced on the internet as a novel designer steroid in dietary supplements around 2009.^[1] It was identified in 2015 in over 30 products sold online that listed it as an ingredient on their product label.^[1]

It became a controlled substance in the United States in 2014 with the passage of the Designer Anabolic Steroid Control Act, which explicitly listed it among 27 new steroids as controlled by the Act.

^[1][4][5]

Chemistry

See also: List of androgens/anabolic steroids

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 and a 17α-alkylated derivative of DHT.^[1][2] It is closely related to epitiostanol (2α,3α-epithio-DHT) and mepitiostane (epitiostanol 17-methyloxycyclopentyl ether).^[1]