title: Seized designer supplement named "1-Androsterone": identification as 3β-hydroxy-5α-androst-1-en-17-one and its urinary elimination.
abstract: 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 100mg 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 3β-hydroxy-5α-androst-1-en-17-one, prepared by reduction of 5α-androst-1-ene-3,17-dione with LS-Selectride (Lithium tris-isoamylborohydride), and by nuclear magnetic resonance. Semi-quantitation revealed an amount of 3β-hydroxy-5α-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 (17β-hydroxy-5α-androst-1-en-3-one), 1-androstenedione (5α-androst-1-ene-3,17-dione), 3α-hydroxy-5α-androst-1-en-17-one, 5α-androst-1-ene-3α,17β-diol, and 5α-androst-1-ene-3β,17β-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 5α-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 5α-/5β-androstane-3α,17β-diol and the concentration of 5α-dihydrotestosterone were influenced. 3α-Hydroxy-5α-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.
authors.affiliation: Center for Preventive Doping Research, Institute of Biochemistry, German Sport University Cologne, Am Sportpark Muengersdorf 6, 50933 Cologne, Germany. m.parr@biochem.dshs-koeln.de
authors.forename: Maria K
authors.initials: MK
authors.lastname: Parr
authors.forename: Georg
authors.initials: G
authors.lastname: Opfermann
authors.forename: Hans
authors.initials: H
authors.lastname: Geyer
authors.forename: Folker
authors.initials: F
authors.lastname: Westphal
authors.forename: Frank D
authors.initials: FD
authors.lastname: Sönnichsen
authors.forename: Josef
authors.initials: J
authors.lastname: Zapp
authors.forename: Dorota
authors.initials: D
authors.lastname: Kwiatkowska
authors.forename: Wilhelm
authors.initials: W
authors.lastname: Schänzer
mesh_terms: D000368:Aged; D045930:Anabolic Agents / Q000032:analysis* / Q000493:pharmacokinetics; D015113:Androstane-3,17-diol / Q000652:urine; D000738:Androsterone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000493:pharmacokinetics / Q000652:urine; D019587:Dietary Supplements / Q000032:analysis*; D013196:Dihydrotestosterone / Q000652:urine; D005043:Etiocholanolone / Q000652:urine; D006801:Humans; D008297:Male; D015813:Substance Abuse Detection / Q000379:methods*; D013739:Testosterone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000652:urine
chemical_list: D045930:Anabolic Agents; D013196:Dihydrotestosterone; D015113:Androstane-3,17-diol; D013739:Testosterone; D005043:Etiocholanolone; D000738:Androsterone; C561866:3-hydroxyandrost-1-en-17-one; C520094:1-testosterone