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Androgens and anabolic steroids
Methylepitiostanol
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    Methylepitiostanol

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    Methylepitiostanol
    Methylepitiostanol.svg
    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
    Drug class Androgen; Anabolic steroid; Antiestrogen
    ATC code
    • None
    Legal status
    Legal status
    Identifiers
    • (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
    PubChem CID
    ChemSpider
    UNII
    Chemical and physical data
    Formula C20H32OS
    Molar mass 320.54 g·mol−1
    3D model (JSmol)
    • CC12CCC3C(C1CCC2(C)O)CCC4C3(CC5C(C4)S5)C
    • 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, 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. It is the 17α-methylated derivative of epitiostanol, an AAS and antiestrogen which was formerly used in the treatment of breast cancer in Japan. 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.

    Methylepitiostanol surfaced on the internet as a novel designer steroid in dietary supplements 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

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


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