GC and Capillary Column GC/MS Determination of Synthetic Anabolic Steroids II. 4-Chloro-Methandienone (Oral Turinabol) and Its Metabolites

Abstract

The determination of oral turinabol (4-chloro-17 alpha-methyl-17 beta-hydroxy-1,4-androstadien-3-one) [1] in the 'free' fraction of human urine samples by gas chromatography and capillary column gas chromatography/mass spectrometry was studied. After administration to man, three major metabolites are formed whose structures were identified as 6 beta-hydroxy-turinabol [2], 6 beta, 12-dihydroxy-turinabol [4], and 6 beta, 16-dihydroxy-turinabol [5], respectively. In much smaller quantities at least another three metabolites are excreted, one of which could be identified as 17 epi-turinabol [6]. No measurable amounts of 1 itself were detected in any of the urine samples investigated. The rate of metabolism and urinary excretion is reasonably fast. The total amount of recovered material, in the form of the three main metabolites, is on the order of 15%. Clean-up procedures and chromatographic conditions are presented in detail.

Metabolic studies with promagnon, methylclostebol and methasterone in the uPA+/+-SCID chimeric mice

“…As a conclusion could be stated that in contrast to clostebol, but similar as for 4-chloro-1,2-dehydro-17␣-methyltestosterone (oral turinabol), several polyhydroxylated metabolites were detected after methylclostebol administration [24,25].…”

“…4). This compound was described as 2,3,16,17-tetrol metabolite [24] and is here indicated as 2,16-dihydroxy-DM-AD (Table 2).…”

Detection and mass spectrometric characterization of novel long-term dehydrochloromethyltestosterone metabolites in human urine

“…Due to their availability on the black market, some AAS are more likely to be abused than the others. One of such substances is dehydrochloromethyltestosterone (DHCMT), also known as 4-chloromethandienone or oral-turinabol, a steroid which is remarkable, inter alia, for its relatively fast elimination rate from the body [2,3].…”

“…In 1970 Schubert et al reported the detection of parent steroid, as well as 6␤-hydroxy-, 16␤-hydroxy-and 6␤,16-dihydroxy-DHCMT in post administration urine [4,5]. Afterward, Dürbeck et al identified 6␤-hydroxy-, 6␤,12-dihydroxy-, 6␤,16-dihydroxy-DHCMT and minor amounts of epi-DHCMT, but did not detect parent drug nor 16␤-hydroxy-DHCMT [2]. The presence of 6␤-hydroxy-DHCMT in human urine was also confirmed [6].…”

Simultaneous determination of nandrolone, testosterone, and methyltestosterone by multi‐immunoaffinity column and capillary electrophoresis

“…However, the specificity and conformation of RIA are not good and it is hard to pursue structure identification, thus GC/MS is used to verify the positive results followed RIA screening [10]. In the intermediate stage of the 1980s, GC/MS has become the widespread measurement method of steroids and their metabolites [11][12][13]. At the present time, GC/MS has been developed as the relatively sophisticated analytical method of the determination of androgenic-anabolic steroids, and it is the common adopted technique of the laboratory for the abused drug analysis all over the world up to the presence [14][15][16].…”