4- Methyltestosterone

In 1959 Clinton and coworkers reported the first synthesis of some pyrazole fused androstane derivatives and described their biological activity (B-76MI40404). Stanazolol (695) or 17-methyl-2iT-5o -androst-2-eno[3,2-c]pyrazol-17/3-ol was 10 times as active as 17a -methyltestosterone in improving nitrogen retention in rats (B-80MI40406), and its myotrophic activity was only twice that of 17a-methyltestosterone. It is used as an anabolic steroid with no lasting adverse side effects. 

Under mild conditions and in a variety of solvents, tertiary steroid alcohols are inert to the fluoroamine. At elevated temperatures, however, they afford exclusively, and in high yield, products resulting from dehydration with or without rearrangement. Thus, 17a-methyltestosterone (10) furnishes in 42% yield the 18-norsteroid (11). 

The orally effective androgen 17a-methyltestosterone (51) is prepared from 3jS-hydroxyandrost-5-en-17-one (49) by treatment with methylmagnesium iodide to give the 17a-methyl compound (50) which is then oxidized to yield... 

Treatment of 4-methyltestosterone under the same conditions affords 17 -hydroxy-4,4-dimethyl-5a-androstan-3 One in about 60% yield while 17jS-hydroxyandrosta-4,6-dien-3-one gives only a low yield of 17 -hydroxy-4,4-dimethylandrost-5-en-3-one. ... 

Chemical proof for the configuration of the three-membered ring is obtained by conversion of compounds (18) and (19), the known la- and Ifi-methyltestosterone acetates. 

Hydroxylation of the double bond of methyltestosterone by means of osmium tetroxide and hydrogen peroxide affords the 4,5 diol. This undergoes beta elimination on treatment with base to yield oxymestrone (83). ... 

Methyltestosterone Testosterone Testosterone Cypionate Testosterone Decanoate Testosterone Propionate... 

Alternatively, as described in U.S. Patent 3,341,557, 6-dehydro-17-methyltestosterone may be used as the starting material. A mixture of 0.4 g of cuprous chloride, 20 ml of 4 M methylmagnesium bromide in ether and 60 ml of redistilled tetrahydrofuran was stirred and cooled in an ice bath during the addition of a mixture of 2.0 g of 6-dehydro-l 7-methyl-testosterone, 60 ml of redistilled tetrahydrofuran and 0.2 g of cuprous chloride. The ice bath was removed and stirring was continued for four hours. Ice and water were then carefully added, the solution acidified with 3N hydrochloric acid and extracted several times with ether. The combined ether extracts were washed with a brine-sodium carbonate solution, brine and then dried over anhydrous magnesium sulfate, filtered and then poured over a 75-g column of magnesium silicate (Florisil) packed wet with hexanes (Skellysolve B). The column was eluted with 250 ml of hexanes, 0.5 liter of 2% acetone, two liters of 4% acetone and 3.5 liters of 6% acetone in hexanes. 

Qi-Hydroxy-17-methyltestosterone p-Toluene sulfonyl chloride Hydrogen fluoride... 

Alprenolol HCl Bromelain Ciprofibrate Clortermine HCl Desonide Fenofibrate Flucloronide Flunisolide Fluocinonide Flurandrenolide Glucagon Gramicidin Hetacillin potassium I proniazid Kebuzone Methyltestosterone Niaprazine Probucol Relaxin Somatotropin Triamcinolone acetonide Acetonitrile... 

Penicillin G hydrabamine Dehydroabietyl ethylene diamine Penicillin V hydrabamine 1 -Dehydro-6tt-methyl-9a-fluorohydro-cortisone Fluorometholone 6-Dehydro-17-methyltestosterone Calusterone... 

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