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Steroids Apr 1995Hydroxylation at position 6 beta testosterone I (17 beta-hydroxyandrost-4-en-3-one) and the anabolic steroids 17 alpha-methyltestosterone II (17 beta-hydroxy-17...
Hydroxylation at position 6 beta testosterone I (17 beta-hydroxyandrost-4-en-3-one) and the anabolic steroids 17 alpha-methyltestosterone II (17 beta-hydroxy-17 alpha-methylandrost-4-en-3-one), metandienone III (17 beta-hydroxy-17 alpha-methylandrosta-1,4-dien-3-one), 4-chloro-1,2-dehydro-17 alpha-methyltestosterone IV (4-chloro-17 beta-hydroxy-17 alpha-methylandrosta-1,4-dien-3-one), and fluoxymesterone V (9-fluoro-11 beta, 17 beta-dihydroxy-17 alpha-methylandrost-4-en-3-one) was achieved via light-induced autooxidation of the corresponding trimethysilyl 3,5-dienol ethers dissolved in isopropanol or ethanol. The reaction further yielded the 6 alpha-hydroxy isomer in low amounts. The 6 beta-hydroxy isomer of I-V and the 6 alpha-hydroxy isomers of I, III, and IV were isolated and characterized by 1H and 13C NMR, high-performance liquid chromatography, gas chromatography, and mass spectrometry. Human excretion studies with single administered doses of boldenone (17 beta-hydroxyandrosta-1,4-dien-3-one), 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, metandienone, 17 alpha-methyltestosterone, and [16,16,17-2H3] testosterone showed that 6 beta-hydroxylation is the major metabolic pathway in the metabolism of 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, and metandienone, whereas for boldenone, 17 alpha-methyltestosterone, and testosterone, 6 beta-hydroxylation is negligible.
Topics: Adult; Anabolic Agents; Chromatography, Gas; Chromatography, High Pressure Liquid; Fluoxymesterone; Humans; Hydrolysis; Hydroxylation; Hydroxytestosterones; Magnetic Resonance Spectroscopy; Male; Mass Spectrometry; Methandrostenolone; Methyltestosterone; Oxidation-Reduction; Photolysis; Solvents; Testosterone
PubMed: 8539789
DOI: 10.1016/0039-128x(95)00008-e -
A.M.A. American Journal of Diseases of... Sep 1951
Topics: Androgens; Humans; Infant; Infant, Newborn; Infant, Premature; Methyltestosterone
PubMed: 14867787
DOI: 10.1001/archpedi.1951.02040040337005 -
Naika. Internal Medicine Dec 1962
Topics: Cortisone; Hypopituitarism; Methyltestosterone
PubMed: 13977810
DOI: No ID Found -
The Journal of Biological Chemistry Apr 1962
Topics: Methyltestosterone; Testosterone
PubMed: 14493684
DOI: No ID Found -
Journal of Chromatographic Science Sep 2020An environmentally friendly method for the determination of testosterone and methyltestosterone by acid-base-induced deep eutectic solvents liquid-liquid microextraction...
An environmentally friendly method for the determination of testosterone and methyltestosterone by acid-base-induced deep eutectic solvents liquid-liquid microextraction (DES-ABLLME) combining with high-performance liquid chromatography was established. The deep eutectic solvent (DES) consisting of menthol:lauric acid:decanoic acid (3:1:1) can act as both hydrogen bond donor and hydrogen bond acceptor. In this approach, ammonia solution (NH3•H2O) is used as an emulsifier to react with DESs in the extraction process to generate salt and form milky white solution, achieving high extraction efficiency. Hydrochloric acid was used as a phase separator to change the emulsification state and promote the separation of extraction agent from water phase. A series of parameters were optimized including the volume of DES and the emulsifying agent, glucose concentration as well as hydrochloric acid volume. The method was linear in the range 0.5-100 μg mL-1 with a correlation coefficient (R) of 0.9999, and the limits of detection were 0.067 and 0.2 μg mL-1 for testosterone and methyltestosterone, respectively. This method was applied to analyze testosterone and methyltestosterone in milk samples, and the recoveries were between 89.2 and 108.2%.
Topics: Animals; Chromatography, High Pressure Liquid; Drug Residues; Glucose; Hydrochloric Acid; Limit of Detection; Linear Models; Liquid Phase Microextraction; Methyltestosterone; Milk; Reproducibility of Results; Testosterone
PubMed: 32798218
DOI: 10.1093/chromsci/bmaa051 -
Journal of Lipid Research Jan 196817alpha-Methyltestosterone-4-(14)C was fed to two dogs in an experiment to determine tissue localization and metabolic disposition of this hypocholesterolemic steroid....
17alpha-Methyltestosterone-4-(14)C was fed to two dogs in an experiment to determine tissue localization and metabolic disposition of this hypocholesterolemic steroid. No accumulation of the drug was found in any tissue, although a small amount of radioactivity was detected in the liver and the ileal mucosa of one animal. Most of the administered radio-activity was excreted in urine and feces. The urinary metabolites consisted largely of highly polar compounds which appeared resistant to glucuronidase treatment or solvolysis procedures. Analysis of the fecal metabolites showed the presence of unchanged methyltestosterone, of four isomeric methylandrostanediols, and of labeled unidentified polar compounds. Of the four identified methylandrostane-diols, the predominating fecal diols were 17alpha-methyl-5alpha-androstane-3beta,17beta-diol (45-62%) and 17alpha-methyl-5-androstane-3alpha,17-diol (12-28%); 17alpha-methyl-5alpha-androstane-3alpha,-17-diol and the 5beta:3beta isomer were found in very small amounts only.
Topics: Androstanes; Animals; Carbon Isotopes; Chromatography, Gas; Chromatography, Thin Layer; Dogs; Feces; Female; Ileum; Infrared Rays; Liver; Male; Methyltestosterone; Spectrum Analysis
PubMed: 5637435
DOI: No ID Found -
European Journal of Endocrinology Jan 2006There has been a growing interest in treating postmenopausal women with androgens. However, hyperandrogenemia in females has been associated with increased risk of... (Randomized Controlled Trial)
Randomized Controlled Trial
BACKGROUND
There has been a growing interest in treating postmenopausal women with androgens. However, hyperandrogenemia in females has been associated with increased risk of cardiovascular disease.
OBJECTIVE
We aimed to assess the effects of androgen replacement on cardiovascular risk factors.
DESIGN
Thirty-seven postmenopausal women aged 42-62 years that had undergone hysterectomy were prospectively enrolled in a double-blind protocol to receive, for 12 months, percutaneous estradiol (E2) (1 mg/day) combined with either methyltestosterone (MT) (1.25 mg/day) or placebo.
METHODS
Along with treatment, we evaluated serum E2, testosterone, sex hormone-binding globulin (SHBG), free androgen index, lipids, fibrinogen, and C-reactive protein; glucose tolerance; insulin resistance; blood pressure; body-mass index; and visceral and subcutaneous abdominal fat mass as assessed by computed tomography.
RESULTS
A significant reduction in SHBG (P < 0.001) and increase in free testosterone index (P < 0.05; Repeated measures analysis of variance) were seen in the MT group. Total cholesterol, triglycerides, fibrinogen, and systolic and diastolic blood pressure were significantly lowered to a similar extent by both regimens, but high-density lipoprotein cholesterol decreased only in the androgen group. MT-treated women showed a modest rise in body weight and gained visceral fat mass relative to the other group (P < 0.05), but there were no significant detrimental effects on fasting insulin levels and insulin resistance.
CONCLUSION
This study suggests that the combination of low-dose oral MT and percutaneous E2, for 1 year, does not result in expressive increase of cardiovascular risk factors. This regimen can be recommended for symptomatic postmenopausal women, although it seems prudent to perform baseline and follow-up lipid profile and assessment of body composition, especially in those at high risk of cardiovascular disease.
Topics: Abdominal Fat; Acute-Phase Proteins; Administration, Oral; Adult; Blood Glucose; Blood Pressure; C-Reactive Protein; Estrogen Replacement Therapy; Female; Fibrinogen; Humans; Hysterectomy; Lipids; Methyltestosterone; Middle Aged; Ovariectomy; Postmenopause; Sex Hormone-Binding Globulin
PubMed: 16382002
DOI: 10.1530/eje.1.02065 -
Meat Science Jan 2010This paper describes the development, validation and application of a confirmatory method to detect 17alpha-methyltestosterone (MT) in bovine hair, to aid in controlling...
This paper describes the development, validation and application of a confirmatory method to detect 17alpha-methyltestosterone (MT) in bovine hair, to aid in controlling the administration of this growth promoter in meat-producing animals. After cryogenic grinding, MT was removed from the hair matrix using a single step extraction procedure with acetonitrile. Hydroxylamine derivatisation was used to enhance analyte determination with an electrospray ionisation (ESI) source. Determination was carried out using a triple quadrupole liquid chromatography tandem mass spectrometer (LC-MS/MS) in multiple reaction monitoring mode (MRM). The method was validated in accordance with the criteria defined in Commission Decision 2002/657/EC and using deuterated testosterone (T-d(3)) as the internal standard. The decision limit (CCalpha) was 0.07 ng g(-1) and the detection capability (CCbeta) was 0.12 ng g(-1). Repeatability was CV% (7%), within-laboratory reproducibility was CV% (11.0%), and trueness was (87%). Applicability of the method was demonstrated in an animal study. Samples obtained from animal experiments were analyzed and the presence of MT was confirmed.
Topics: Anabolic Agents; Analytic Sample Preparation Methods; Androgens; Animals; Calibration; Cattle; Chromatography, High Pressure Liquid; Drug Residues; Food Contamination; Hair; Hydroxylamine; Limit of Detection; Methyltestosterone; Pigmentation; Reproducibility of Results; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry
PubMed: 20374774
DOI: 10.1016/j.meatsci.2009.08.047 -
Journal of Pharmaceutical and... 1991A simple gas chromatographic procedure has been developed for the determination of methyltestosterone in bulk powders and in tablets. Two new silyl ether derivatives of...
A simple gas chromatographic procedure has been developed for the determination of methyltestosterone in bulk powders and in tablets. Two new silyl ether derivatives of methyltestosterone have been prepared using dimethylethylsilylimidazole (DMESI) and dimethylisopropylsilylimidazole (DMiPSI). The method is accurate and selective for methyltestosterone within the concentration range 0.1-1.5 micrograms microliters-1.
Topics: Chromatography, Gas; Methyltestosterone; Tablets
PubMed: 1821146
DOI: 10.1016/0731-7085(91)80210-z -
Environmental Toxicology and Chemistry Mar 2004Abstract-We studied the chronic effects of methyltestosterone (MT) on reproductive status of medaka (Oryzias latipes) over two generations under continuous exposure to... (Comparative Study)
Comparative Study
Abstract-We studied the chronic effects of methyltestosterone (MT) on reproductive status of medaka (Oryzias latipes) over two generations under continuous exposure to verify the applicability of the fish full life-cycle test (FFLC) for this androgen with this species. The exposure of parental (F0) medaka to MT was begun on embryos within 12 h postfertilization and continued for up to 101 d; assessment endpoints included embryological development, hatching, posthatch survival, growth, sexual differentiation, reproduction, and hepatic vitellogenin (VTG) levels under flow-through exposure to MT at each mean measured concentration of 0.35, 1.09, 3.29, 9.98, and 27.75 ng/L. Eggs (F1) spawned from the F0 fish at 98, 99, and 100 d posthatch were examined for hatchability, survival after hatching, growth, sexual differentiation, and hepatic VTG level until 60 d posthatch. In the FFLC with medaka, MT induced masculinization of both secondary sex characteristics and gonads. We observed that all F0 fish in the 27.75-ng/L treatment group showed male secondary sex characteristics in which no fish with ovary could be discerned. Several fish with ovaries in F0 and F1 generations treated with 9.98 ng/L showed male secondary sex characteristics. We also observed swollen abdomens in the F0 and F1 female fish in the 9.98-ng/L treatment group. These swollen abdomens were induced by enlarged ovaries and were accompanied with declined fecundity and fertility in the F0 generation. These results indicate that MT reduces the reproductive potential of medaka and that the FFLC with this species is applicable to the evaluation of androgens.
Topics: Animals; Dose-Response Relationship, Drug; Environmental Monitoring; Female; Gonads; Histological Techniques; Japan; Liver; Male; Methyltestosterone; Oryzias; Reproduction; Sex Characteristics; Sex Differentiation; Vitellogenesis; Water Pollutants, Chemical
PubMed: 15285372
DOI: 10.1897/03-26