Seized designer supplement named 1-Androsterone: Identification as 3β-hydroxy-5α-androst-1-en-17-one and its urinary elimination

New analogues of androgens that had never been available as approved drugs are marketed as dietary supplement recently. They are mainly advertised to promote muscle mass and are considered by the governmental authorities in various countries, as well as by the World Anti-doping Agency for sport, as being pharmacologically and/or chemically related to anabolic steroids. In the present study, we report the detection of a steroid in a product seized by the State Bureau of Criminal Investigation Schleswig-Holstein, Germany. The product 1-Androsterone of the brand name Advanced Muscle Science was labeled to contain 100 mg of 1-Androstene-3b-ol,17-one per capsule. The product was analyzed underivatized and as bis-TMS derivative by GC-MS. The steroid was identified by comparison with chemically synthesized 3 beta-hydroxy-5 alpha-androst-1-en-17-one, prepared by reduction of 5 alpha-androst-1-ene-3,17-dione with LS-Selectride (Lithium tris-isoamylborohydride), and by nuclear magnetic resonance. Semi-quantitation revealed an amount of 3 beta-hydroxy-5 alpha-androst-1-en-17-one in the capsules as labeled. Following oral administration to a male volunteer, the main urinary metabolites were monitored. 1-Testosterone (17 beta-hydroxy-5 alpha-androst-1-en-3-one), 1-androstenedione (5 alpha-androst-1-ene-3,17-dione), 3 alpha-hydroxy-5 alpha-androst-1-en-17-one, 5 alpha-androst-1-ene-3 alpha,17 beta-diol, and 5 alpha-androst-1-ene-3 beta,17 beta-diol were detected besides the parent compound and two more metabolites (up to now not finally identified but most likely C-18 and C-19 hydroxylated 5 alpha-androst-1-ene-3,17-diones). Additionally, common steroids of the urinary steroid profile were altered after the administration of 1-Androsterone. Especially the ratios of androsterone/etiocholanolone and 5 alpha-/5 beta-androstane-3 alpha,17 beta-diol and the concentration of 5 alpha-dihydrotestosterone were influenced. 3 alpha-Hydroxy-5 alpha-androst-1-en-17-one appears to be suitable for the long-term detection of the steroid (ab-)use, as this characteristic metabolite was detectable in screening up to nine days after a single administration of one capsule. (C) 2011 Elsevier Inc. All rights reserved.