An Analytical Profile of Oral-Turinabol ( Dehydrochlormethyltestosterone)It is the 4-chloro-substituted derivative of metandienone dehydromethyltestosterone. The patent registration took place in The idea of combining the dehydrochlormethyltestosterone detection of 4-chlorotestosterone clostebol and metandienone originated from the chemist Albert Stachowiak. CDMT was the key steroid administered to approximately deetction, athletes from East Germany GDR dehydrochlormethyltestosterone detection secret official policy, often without their knowing the nature of the "vitamins" they were forced to take. The doping program was run by the East German Government from about until when the Berlin Wall was destroyed.
Chlorodehydromethyltestosterone - Wikipedia
Despite identical appearances same bottle type, labeling, lot number, and number of tablets , some of the bottles contained nondescript orange capsules while other bottles contained nondescript yellow capsules see Photo 2. Subsequent analyses confirmed that the orange capsules contained dehydrochlormethyltestosterone as the only active ingredient, while the yellow capsules contained primarily dehydrochlormethyltestosterone with minor amounts of stanozolol and methandrostenolone see structures, below.
It gained notoriety as a result of the East German Olympic doping scandals that were fully exposed after the fall of the Berlin wall 2. Data from East German medical personnel involved in the doping indicated that dehydrochlormethyltestosterone produced dramatic increases in speed and strength, but with detrimental side effects such as deepening of the voice, increased acne, and body hair growth.
Other, long term side-effects ranged from liver damage to severe gynaecological disorders 2. This steroid is no longer legitimately produced, and appears to be available only as an illicitly-prepared product on the black market.
Dehydrochlormethyltestosterone with Labeling of Rings A-D. As with nearly all anabolic steroids, dehydrochlormethyltestosterone has multiple name variations, including but not limited to: Not surprisingly, most of the scientific literature dedicated to the analysis of dehydrochlormethyltestosterone has a toxicological focus that is, analysis of biological fluids for dehydrochlormethyltestosterone metabolites for detection of doping 4,5.
Although there are a number of reports of submissions of dehydrochlormethyltestosterone to forensic and crime laboratories 6 , complete forensic analysis of dehydrochlormethyltestosterone has not been previously reported, and even standard reference texts in the field e. In addition, because this is the first comprehensive report for this steroid, an in-depth analysis of the NMR data is presented.
A reference standard of dehydrochlormethyltestosterone was obtained from Steraloids Newport, RI. The sample was prepared by extraction of the capsule matrix with methanol followed by evaporation.
The IR spectrum was collected by averaging 24 scans with a resolution of 4. GC Relative Retention Times. The sample was dissolved in methanol and injected into the instrument using the parameters below The sample was dissolved in methanol and injected into the instrument using the parameters below. The chromatogram is not shown. Methandrostenolone, dehydrochlormethyltestosterone, and stanozolol eluted at 7. The peak shape for stanozolol was broad in comparison to the other steroids.
The mixture in the yellow tablets was not formally quantitated, but was estimated as roughly Instrumental parameters are listed below. The mass spectra of dehydrochlormethyltestosterone, methandrostenolone, and stanozolol are shown in Figures 1 — 3, respectively. Analysis of the molecular ion cluster i. Theoretical versus Actual Values for the Relative Abundances. The IR spectrum of the reference standard is shown in Figure 4.
Comparison of the reference standard with the sample is shown in Figure 5. The direct comparison did not show a high quality match; it is suspected that either polymorphism or the presence of other soluble capsule materials in the extract caused the differences in the spectra.
The chromatograms for dehydrochlormethyltestosterone standard and a mixture of dehydrochlormethyltestosterone and stanozolol standards roughly 5: The two peaks resulting from the dehydrochlormethyltestosterone - stanozolol mixture did not resolve using this method inset in Figure 6.
Table 3 lists the relative retention times of a series of similarly sized steroids. Figure 7 shows the UV spectrum of dehydrochlormethyltestosterone. The Inset Shows the Chromatogram for the 5: The proton, carbon, and HSQC experiments showed that the unknown molecule contained 20 carbons and 26 non-exchangeable hydrogens. There were 6 quaternary, 5 methine, 6 methylene, and 3 methyl carbons.
Adding the carbons 20 , non-labile protons 26 , oxygens 2 , and chlorine 1 based on the MS data , gives a molecular weight of Daltons. The remaining mass 1 Dalton is due to an exchangeable proton. Far removed is a quaternary carbon at Assuming that this is a common steroid ring structure, placement of the carbon 82 ppm bonded to oxygen would be at the 17 position.
This accounts for all but the methyl group, and since the 82 ppm carbon is a quaternary carbon, the methyl group is attached at the 17 position. Comparison of the experimental data with that predicted with the ACD software showed very good agreement. In addition, comparison of the 1H-NMR spectrum of the unknown to methandrostenolone showed they were nearly identical below 2. NMR Data and Assignments. Franke WW, Berendonk B. Hormonal doping and androgenization of athletes: A secret program of the German Democratic Republic government.
Clinical Chemistry ;43 7: In Drug Abuse Handbook, S. Criminalistics - Introduction to controlled substances, pp. Novel mass spectrometric analysis for anabolic androgenic steroids in sports drug testing.
Mass Spectral and GC Data, 2nd ed. Instrumental Data for Drug Analysis, 2nd ed. Submitted by RonnyT on Wed, HPLC Relative Retention Times Asterisks denote steroids analyzed at an earlier date; the retention times were adjusted relative to the dehydrochlormethyltestosterone. Login to post comments.