Steroids. CV.¹ 2-Methyl and 2-Hydroxymethylene-androstane Derivatives

Anabolic steroids detected in bodybuilding dietary supplements – a significant risk to public health

“…[1] Similar to the 'legal highs' phenomenon, [5,6] and to some degree overlapping, [7][8][9][10][11][12] this market has been driven by opportunists [13] who have searched the scientific and patent literature for active substances, which were often originally synthesized as part of academic and pharmaceutical research programmes but were not commercialized as medicines. [14][15][16][17][18][19][20] Importantly, when such products containing anabolic steroids first emerged in the mid to late 1990s in the United States, the substances were also selected on the basis that they were not subject to drug control laws at that time. [21,22] Most of the anabolic steroids used in these products are produced in bulk and obtained from wherever they can be cheaply and reliably sourced, imported into countries such as the United States and the United Kingdom where they are processed and packaged into finished products and sold in bricks-and-mortar and online fitness equipment shops; their sale as 'dietary supplements' appears to be a ploy to circumvent regulatory systems such as those governing medicines.…”

Mass spectrometric description of novel oxymetholone and desoxymethyltestosterone metabolites identified in human urine and their importance for doping control

“…Oxymetholone (2‐hydroxymethylene‐17α‐methyl‐17β‐hydroxy‐5α‐androstan‐3‐one) and desoxymethyltestosterone (17α‐methyl‐17β‐hydroxy‐5α‐androst‐2‐en) are the examples of AAS featuring 17α‐methyl group, which makes the steroids orally active . While oxymetholone, known since 1960s, is a prescription drug currently approved in several countries for the treatment of anemia and HIV‐related muscle wasting, desoxymethyltestosterone was not marketed until 2005 when it was identified in a clandestine product by Sekera et al . and independently by a group of Canadian scientists at the Institut national de la recherche scientifique (INRS) .…”

“…Oxymetholone (2-hydroxymethylene-17a-methyl-17b-hydroxy-5a-androstan-3-one) and desoxymethyltestosterone (17a-methyl-17b-hydroxy-5a-androst-2-en) are the examples of AAS featuring 17a-methyl group, which makes the steroids orally active. [3] While oxymetholone, known since 1960s, [4] is a prescription drug currently approved in several countries for the treatment of anemia and HIV-related muscle wasting, [5] desoxymethyltestosterone was not marketed until 2005 when it was identified in a clandestine product by Sekera et al [6] and independently by a group of Canadian scientists at the Institut national de la recherche scientifique (INRS). [7,8] Soon after, desoxymethyltestosterone shown to be a potent agonist of anabolic receptors [9] became available as a component of sport nutritional supplements under the non-systematic names 17a-methyl-etioallocholan-2-en-17b-ol or 17-methyl-delta-2-etioallocholan.…”

A review of designer anabolic steroids in equine sports

“…). It has been reported in the older steroid literature to exert a strong anabolic effect in rats, and predicted to be a potent anabolic agent in a more recent computational study . It has been reported as a component of the dietary supplements Superdrol (Anabolic Xtreme), S‐drol (Black China Labs), and Methasterone (Legal Gear) .…”