Sense or nonsense of prohormone designing : reduced metandienone as supplement
Deutscher übersetzter Titel: | Sinn und Unsinn bei der Herstellung von Prohormonen : reduziertes Metandienon als Nahrungsergänzungsmittel |
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Autor: | Parr, M.K.; Opfermann, G.; Schlörer, N.; Geyer, Hans; Rataj, Felicitas; Zierau, Oliver; Dici, P.; Schänzer, Wilhelm |
Erschienen in: | Recent advances in doping analysis (19) : Proceedings of the Manfred-Donike-Workshop ; 29th Cologne Workshop on Dope Analysis ; 13th to 18th February 2011 |
Veröffentlicht: | Köln: Sportverl. Strauß (Verlag), 2011, S. 15-23, Lit. |
Format: | Literatur (SPOLIT) |
Publikationstyp: | Sammelwerksbeitrag |
Medienart: | Elektronische Ressource (Datenträger) |
Sprache: | Englisch |
Schlagworte: | |
Online Zugang: | |
Erfassungsnummer: | PU201211007398 |
Quelle: | BISp |
Abstract
Since the mid of the 1990s anabolic steroids are marketed as dietary supplements by labeling them as so-called ‘prohormones’. The first prohormones on the market were derived from Testosterone and Nortestosterone by oxidation or reduction at C3 or C17 yielding (19-nor)androst-4-or-5-ene-3,17-dione or-diols. Recently, products were found on the market stating to contain “17α-methyl-1,4-androstadiene-3,17-diol”. These products were analyzed for their steroid content following soxhlett extraction with n-hexane using GC-MS of the underivatized compound and its per-TMS derivative. Additionally, NMR data were recorded to confirm the structure. Differing from the label, the derived structure was confirmed as 4,l7-dimethylestra-1,3,5-trien-l7β-ol. Reproducing the reduction of the oxo—group on C3 of metandienone with lithium aluminium hydride or sodium borohydride under different conditions most likely provides the explanation: water was directly eliminated from the intermediate in a reaction called benzene-hydroxy dienol rearrangement. To characterize the biological activity of 4,17-dimethylestra-1,3,5-trien-l7β-ol it was tested in yeast androgen and estrogen receptor transactivation assays for agonistic and antagonistic effects. None of the assays resulted in any transactivation. Additionally, it was studied in a rat animal model. Orchiectomized rats were treated s.c. for 12 days with 1 mg/kg BW/day. Tissue wet weights were determined to indicate the anabolic (m. lev. ani) and androgenic (prostate) activity, which were confirming the inactivity of this substance. Verf.-Referat