Methyl-1-testosterone

Oral mucosal membranes provide a port for systemic therapy as weU. Nitroglycerin sublingual tablets (Nitrostat) abort acute mgina attacks methyl-testosterone [58-18-4] buccal tablets (Android 5) are indicated for testosterone [58-22-0] replacement therapy (39) md nicotine [54-11-5] gum (Nicorette) aids in smoking cessation. 

A highly modified methyl testosterone derivative also exhibits antiandrogenic activity. One synthesis of this compound Involves initial alkylation of methyl testosterone (3 ) by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative Formylation with alkoxide and... 

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. 

Bacterium Didymella lycopersici 17/J-Methyl testosterone Selenium dioxide... 

To two liters of a culture so prepared there is added under sterile conditions a solution of 500 mg of 17a-methyl-testosterone in 15 cc of acetone. Shaking is carried out for 3 days at 27°C, the mycellium then filtered off with suction, washed with water and ethyl acetate and the combined filtrates extracted with ethyl acetate. The extraction residue obtained after evaporation of the solvent is dissolved in a little acetone. On addition of ether, the 1-dehydro-17a-methyl-testosterone is obtained in compact crystals. MP 163° to 164°C. 

The ethyl acetate solution is then washed with water, dried and evaporated. To remove any selenium still present, the residue is dissolved in 200 cc of methanol and mixed with 100 g of iron powder and 2 g of active carbon. The mixture is heated for 30 minutes with stirring under reflux, then filtered with suction, washed with methanol and the solution evaporated in vacuo. The residue is then chromatographed on 900 g of aluminum oxide. The residues of the evaporated benzene and ether fractions are treated with active carbon in methanol or acetone, evaporated again, and the residue recrystallized from a mixture of acetone and ether. There are obtained 17.5 g of pure 1-dehydro-17a-methyl-testosterone which melts at 163° to 164°C. 

Methyl testosterone Hypogonadism, delayed puberty Oreton Methyl, Testred, Virilon... 

Testosterone and its derivatives can be administered in several ways. Fluoxymesterone and methyl-testosterone are 17-alpha-alkylated derivatives which are active when administered orally. 

Methyl testosterone (Android, Virilon, and Testrad) Potential for prostatic hypertrophy and cardiac problems. High... 

Gharavi, M., K. C. James, and L. H. Sanderds. 1983. Solubilities of mestanolone, methandienone, methyl-testosterone, nandrolone, and testosterone in homologous series of alkanes and Wkahcffbarm. 14 333-341. 

A suspension of 30 g of 17a-methyl-testosterone and 10 g of selenium dioxide in 600 cc of tertiary amyl alcohol is treated with 60 g of magnesium powder and 6 cc of glacial acetic acid. 

B) The cyclopentyl enolether of androstenedione was converted to the corresponding cyclopentyl enolether of 17a-methyl testosterone as follows ... 

FIGURE 5-1. Determining an appropriate mobile phase for known standards. Column Bondapak C 8/Corasil (pellicular) 2.3 mm ID x 61 cm. Mobile phase acetonitrile/water (40/60, 30/70, 20/80, and 25/75 denoted on chromatogram). Sample components (1) hydrocortisone (2) hydrocortisone acetate (3) estrone and (4) methyl testosterone. Detector UV at 254 nm. 

Miscellaneous Additions.-The conversion of testosterone into 4-methyl-testosterone via a modified Simmons-Smith methylenation of the A3,5-dien-3-yl trimethylsilyl ether104 has now been varied by employing the A2,4-dien-3-yl trimethylsilyl derivative (86), produced by trapping the kinetically controlled A2,4-dienolate. The end product, via (87), was 2a-methyltestosterone (88).105... 

Bendroflumethiazide Dosage forms HPLC phase + 1STD (methyl testosterone) Dissolve in MeOH- Phenyl, 7... 

Isotestosterone and 8a, 1 Oa-testosterone can be considered as substituted testosterone derivatives where the 8-H is substituted by an alkyl group. In the case of 8a,10a-testosterone other structural features are prohibitive for biological activity. However, 8-isotestosterone displays decreased, but definite androgenic and anabolic properties. Nagata [160] prepared some 8/3-substituted testosterone homologs —8-methyl-testosterone (E-30) and others. In all cases decreased androgenic and anabolic potencies were observed. These facts point to the importance of /3-face attachment to the receptor at carbon-8. 

---