Methylepitiostanol
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| Clinical data | |
|---|---|
| Routes of administration | Oral[1] |
| ATC code | None |
| Identifiers | |
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| Synonyms | Methylepithiostanol; Methepitiostane; 2α,3α-Epithio-3-deketo-17α-methyl-4,5α-dihydrotestosterone |
| CAS Number | 4267-80-5 |
| PubChem (CID) | 71752521 |
| ChemSpider | 48063843 |
| UNII | Z50OE1022B |
| Chemical and physical data | |
| Formula | C20H32OS |
| Molar mass | 320.53248 g/mol |
| 3D model (Jmol) | Interactive image |
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Methylepitiostanol (online product names Epistane, Hemapolin, Havoc, Epi Plex),[2] also known as 17α-methylepitiostanol or 2α,3α-epithio-17α-methyl-5α-androstan-17β-ol, is a synthetic androgenic-anabolic steroid (AAS) that was first described in the literature in 1974 but was never marketed.[1][3] It is the 17α-methylated derivative of epitiostanol, an AAS and antiestrogen formerly used in the treatment of breast cancer in Japan, and similarly to mepitiostane (epitiostanol 17-methyloxycyclopentyl ether), is an orally active version of epitiostanol.[1][3] Due to its 17α-methyl group, methylepitiostanol is considered to have a high potential for hepatotoxicity.[1] The drug 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] As of 2015, the drug is reportedly not a controlled substance.[1] However, methylepitiostanol may degrade in some product containers into desoxymethyltestosterone, which, in contrast, is a controlled substance.[1][4] Methylepitiostanol is reported to be a prodrug of desoxymethyltestosterone.[5]
References
- 1 2 3 4 5 6 7 8 Rahnema, C. D.; Crosnoe, L. E.; Kim, E. D. (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. ISSN 2047-2927. PMID 25684733.
- ↑ https://pubchem.ncbi.nlm.nih.gov/compound/71752521
- 1 2 Miyake, Tamotsu; Uchida, Kiyohisa; Kakushi, Hisato; Nomura, Yasuharu; Kadowaki, Masumi; Miyata, Kenji; Hanafusa, Tomoyuki; Muranaka, Ri-ichi (1974). "2α, 3α-EPITHIO-5α-ANDROSTAN-17β-YL 1-METHOXY CYCLOPENTYL ETHER (10364-S), A NEW ORALLY ACTIVE ANABOLIC-ANDROGENIC STEROID". The Japanese Journal of Pharmacology. 24 (4): 551–558. doi:10.1254/jjp.24.551. ISSN 0021-5198.
- ↑ Okano, Masato; Sato, Mitsuhiko; Ikekita, Ayako; Kageyama, Shinji (November–December 2009). "Analysis of non-ketoic steroids 17α-methylepithiostanol and desoxymethyl-testosterone in dietary supplements". Drug Testing and Analysis. 1 (11-12): 518–525. doi:10.1002/dta.72. ISSN 1942-7611. PMID 20355167.
- ↑ Okano M, Sato M, Ikekita A, Kageyama S (2009). "Analysis of non-ketoic steroids 17alpha-methylepithiostanol and desoxymethyl- testosterone in dietary supplements". Drug Test Anal. 1 (11-12): 518–25. doi:10.1002/dta.72. PMID 20355167.