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Methylepitiostanol

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Methylepitiostanol
Clinical data
Other namesEpistane; 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 classAndrogen; 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
FormulaC20H32OS
Molar mass320.54 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.[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 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, being one of the 27 new steroids explicitly listed as controlled by the Act.

[1][4] [5]

Chemistry

[edit]
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]

References

[edit]
  1. ^ a b c d e f g h i j Rahnema CD, Crosnoe LE, Kim ED (March 2015). "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology. 3 (2): 150–155. doi:10.1111/andr.307. PMID 25684733. S2CID 6999218.
  2. ^ a b c d Miyake T, Uchida K, Kakushi H, Nomura Y, Kadowaki M (August 1974). "2alpha, 3alpha-epithio-5alpha-androstan-17beta-yl 1-methoxycyclopentyl ether (10361-S), a new orally active anabolic-androgenic steroid". Japanese Journal of Pharmacology. 24 (4): 551–558. doi:10.1254/jjp.24.551. PMID 4455965.
  3. ^ "2,3-Thioepoxy madol". PubChem. U.S. National Library of Medicine.
  4. ^ Okano M, Sato M, Ikekita A, Kageyama S (November 2009). "Analysis of non-ketoic steroids 17alpha-methylepithiostanol and desoxymethyl- testosterone in dietary supplements". Drug Testing and Analysis. 1 (11–12): 518–525. doi:10.1002/dta.72. PMID 20355167.
  5. ^ Okano M, Sato M, Ikekita A, Kageyama S (November 2009). "Analysis of non-ketoic steroids 17alpha-methylepithiostanol and desoxymethyl- testosterone in dietary supplements". Drug Testing and Analysis. 1 (11–12): 518–525. doi:10.1002/dta.72. PMID 20355167.
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