Androgenic Compounds

The clinical success of the progestational gonanes engendered a corresponding effort toward finding potent orally active androgens in the 19-nor steroid series. The 

One of the important mechanisms by which orally administered steroids are inactivated involves the formation of water-soluble derivatives at the 17 position, a process that is greatly reduced in 17a-alkyl-17(3-hydroxy derivatives. Extensive use of the resulting orally active compounds has since revealed that 17 alkylation also leads to increased liver toxicity. Preparation of the first of these compounds, nor-methandrolone (32-3), starts by addition of methylmagnesium iodide to estrone methyl ether (9-1) to give the 17a methyl derivative. Birch reduction followed by acid hydrolysis leads to normethandrolone (32-3) [16]. 

The synthesis of the homologue norethandrolone starts with catalytic reduction of the side chain unsaturation in mestranol (9-1) to the corresponding ethyl derivative 

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Androgenic compounds occur in various plants. Celery stalks and parsnip roots contain trace amounts of androstenedione (Fig. 11.12), the same compound found in boar odor (Claus and Hoppen, 1979). Testosterone is also found in pollen of Scots pine Pinus sylvestris). 

Androstenedione, dehydroepiandrosterone (DHEA), and dehydroepiandrosterone sulfate (DHEA-S) are other mildly androgenic compounds of secondary importance in males and females. The gonads and the adrenal cortex are capable of secreting androstenedione... 

Anabolic activities of testosterone, such as increases in amino acid incorporation into protein and in RNA polymerase activity, have been demonstrated in skeletal muscle. Apart from the direct anabolic effects in specific tissue, androgens antagonize the protein catabolic action of glucocorticoids. The androgen compounds with the greatest ratio of protein anabolic effects to virilizing effects are the 19-nortestosterone derivatives. Compounds that are used clinically (Table 63.3) include nandrolone phenpropionate (Durabolin), nandrolone decanoate... 

In the Netherlands, about 40,000 urine samples from groups of calves and cattle in the farmhouse are screened every year for the presence of -agonists, corticosteroids, and estrogenic and androgenic compounds. For screening pur-... 

In liquid chromatography, reversed-phase materials such as Cig and Cg are the most commonly used sorbents (429, 430, 434, 438, 446, 447, 453, 454). Examples of baseline separations with reversed-phase columns of several groups of anabolics including stilbenes, resorcyclic acid lactones, and other, frequently used anabolics have been reported (463-466). In addition to reversed-phase separations normal-phase separations of anabolics using either Hypersil (467) and Brownlee (456) silica or diol-modified silica have been reported. Although not all analytes were completely separated, the latter column could be efficiently used to differentiate between estrogenic and androgenic compounds within a mixture of 15 anabolics and their metabolites (468). 

Msagati, T. A. M., Nindi, M. M. (2005). Supported liquid membrane extraction of anabolic androgenic compounds in biological matrices and detection by LC-ESI-MS. South Afr. J. Chem., 58, 67-73. 

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