Anabolic androgenic steroids (AAS) are misused very frequently in sport competitions as performance enhancing agents. One of the doping compounds that has been detected with increased frequency in the last few years is dehydrochloromethyltestosterone (DHCMT, 4-chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one; brand name Oral Turinabol). The long-term DHCMT metabolite 20βOH-NorDHCMT (4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one) was reported earlier to be detectable in urine samples for more than 22 days after DHCMT administration; however, purified reference material was not available so far. In this study we demonstrate a successful combination of Wagner-Meerwein rearrangement of DHCMT to NorDHCMT (4-chloro-17,17-dimethyl-18-norandrosta-1,4,13-trien-3-one) and subsequent whole-cell biotransformation with a recombinant fission yeast strain expressing the human cytochrome P450 enzyme (CYP or P450) CYP21A2 for the synthesis of mg amounts of this metabolite. It was then used as reference for the analysis of a post administration urine of DHCMT. The availability of this reference compound will provide an incontestable proof for DHCMT abuse.

合成代谢雄激素类固醇（AAS）在体育比赛中经常被滥用为增强性能的药物。在最近几年中发现频率增加的一种掺杂化合物是脱氢氯甲基睾丸激素（DHCMT，4-chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one;品牌Oral Turinabol）。据报道，长期DHCMT代谢产物20βOH-NorDHCMT（4-氯-17β-羟甲基-17α-甲基-18-诺兰德罗斯塔-1,4,13-三烯-3-酮）在尿液样本中的检出量超过DHCMT管理后22天；但是，到目前为止尚无纯化的参考材料。在这项研究中，我们证明了DHCMT的Wagner-Meerwein重排与NorDHCMT（4-氯-17,17-二甲基-18-norandrosta-1,4，13-trien-3-one），然后用表达人细胞色素P450酶（CYP或P450）CYP21A2的重组裂变酵母菌株进行全细胞生物转化，以合成毫克量的这种代谢产物。然后将其用作DHCMT给药后尿液分析的参考。该参考化合物的可获得性将为DHCMT滥用提供无可争议的证据。