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Methylepitiostanol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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 nicknamesEpistane,Hemapolin,Havoc, andEpi Plex, is asynthetic andorally activeanabolic–androgenic steroid (AAS) of thedihydrotestosterone (DHT) group which was first described in the literature in 1974 but was never marketed for medical use.[1][2][3] It is the17α-methylated derivative ofepitiostanol, an AAS andantiestrogen which was formerly used in the treatment ofbreast cancer inJapan.[1][2] Similarly tomepitiostane, 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 forhepatotoxicity.[1]

Methylepitiostanol surfaced on the internet as a noveldesigner steroid indietary 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

[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 asyntheticandrostanesteroid and a17α-alkylatedderivative of DHT.[1][2] It is closely related to epitiostanol (2α,3α-epithio-DHT) and mepitiostane (epitiostanol 17-methyloxycyclopentyl ether).[1]

References

[edit]
  1. ^abcdefghijRahnema 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. ^abcdMiyake 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.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
Retrieved from "https://en.wikipedia.org/w/index.php?title=Methylepitiostanol&oldid=1303035968"
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