Synthesis of 6β–chlorotestosterone metabolite(s)

Code: 252C04GH

6β-chlorotestosterone (6β-Cl-T) is a new steroid-like compound reported in the blank market in recent years. Metabolic profile of 6β-Cl-T in human urine after an oral dose of 40 mg was studied in our previous report. Ten new metabolites including four Phase I metabolites and six Phase II metabolites were characterized and potentially identified. Furthermore, the influence on steroidal profile after administration of 6β-Cl-T was evaluated by GC-MS/MS. Results showed that 6β-Cl-T could transform to T in one male volunteer, so as to cause an AAF for T and its metabolites. In order to figure out the origin of T in this male volunteer, GC-C-IRMS was applied in the two samples at abnormal high T/E ratio values of 6.86 and 5.0 (> 4). In total, δ13C values were determined in 5 target compounds (TCs), which were T, 5αAdiol, 5βAdiol, A, and Etio. However there was no significant change in increasing testosterone levels for women individuals and UGT2B17 gene deletion (del/del) male individuals, which might cause false negative results in these people.

The current application is a follow-up study of our previous project, and the objectives of this research are to (1) find the dechlorinated metabolites (biomarkers) and conversion mechanism from 6β-Cl-T to T, aiming to mitigate the drawback of conventional ABP strategies failing to be effective for UGT2B17 gene deletion (del/del) population after medication of 6β-Cl-T, (2) employ biological methodologies for the synthesis, purification, and enrichment of the principal metabolite(s) of 6β-Cl-T, and (3) chemical synthesis of metabolites, and finally distribute metabolite(s) to WADA-accredited doping control laboratories.