| Identification | Back Directory | [Name]
Dromostanolone | [CAS]
58-19-5 | [Synonyms]
Metholone
Medrotestron
Dromostanolone
Drostanolone/Dromostanolone
Dihydro-2α-Methyltestosterone
2α-Methyl-5α-dihydrotestosterone
2α-Methyl-5α-androstan-17β-ol-3-one
2α-Methyl-17β-hydroxyandrostan-3-one
(5α)-2α-Methyl-4,5-dihydrotestosterone
17β-Hydroxy-2α-methyl-5α-androstan-3-one
2α-Methyl-17β-hydroxy-5α-androstan-3-one
(2a,5a,17b)-17-Hydroxy-2-methylandrostan-3-one
(2α,5α,17β)-17-Hydroxy-2-Methylandrostan-3-one
Androstan-3-one,17-hydroxy-2-Methyl-, (2a,5a,17b)-
(2R,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one | [EINECS(EC#)]
200-367-9 | [Molecular Formula]
C20H32O2 | [MDL Number]
MFCD00198322 | [MOL File]
58-19-5.mol | [Molecular Weight]
304.47 |
| Chemical Properties | Back Directory | [Melting point ]
145-147°C | [alpha ]
D +32° (ethanol) | [Boiling point ]
420.3±45.0 °C(Predicted) | [density ]
1.058±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
Acetonitrile: 1 mg/mL; Ethanol: 1 mg/mL; Methanol: 1 mg/mL | [form ]
A crystalline solid | [pka]
15.09±0.70(Predicted) | [CAS DataBase Reference]
58-19-5 | [NIST Chemistry Reference]
Drostanolone(58-19-5) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
Synthetic estrogen antagonist. Antineoplastic.
Controlled substance. | [Description]
Drostanolone, also known as Dromostanolone[58-19-5], is an anabolic hormone and a derivative of methyltestosterone. Its action is similar to that of Conviron. Its anabolic effect is 4 times that of methyltestosterone and its androgenic activity is 0.39 times that of the latter. It is clinically used in the treatment of chronic wasting disease, pediatric underdevelopment, old age and frailty, serious illness and postoperative weakness, osteoporosis, aplastic anemia, leukopenia, thrombocytopenia, and hyperlipidemia. | [Originator]
Drolban,Lilly,US,1961 | [Definition]
ChEBI: Metholone is a 17beta-hydroxy steroid, an anabolic androgenic steroid and a 3-oxo-5alpha-steroid. It has a role as an anabolic agent and an antineoplastic agent. | [Manufacturing Process]
A suspension of 10 grams of dihydrotestosterone in 500 cc of anhydrous
benzene free of thiophene was mixed with10 cc of ethyl formate and 3 grams
of sodium hydride and the mixture was stirred for 5 hours under an
atmosphere of nitrogen and at a temperature of approximately 25°C. The
resulting suspension was filtered, the resulting mixture of the sodium salt of
the hydroxymethylene compound and the excess of sodium hydride was
washed with benzene and dried. This mixture was slowly added to a
vigorously stirred solution of 20 cc of concentrated hydrochloric acid in 500 cc
of water, and the stirring was continued for 30 minutes at the end of which
the precipitate was collected and well washed with distilled water. After drying
in vacuo, there was obtained 9.7 grams of 2-hydroxymethylenedihydrotestosterone.
A mixture of 1 gram of 2-hydroxymethylene-dihydrotestosterone, 10 cc of
pyridine and 2 cc of propionic anhydride was allowed to react at room
temperature for 16 hours and then poured into water. The resulting
suspension was heated for 1 hour on the steam bath to hydrolyze the excess
of propionic anhydride, cooled and extracted with methylene dichloride. The
extract was consecutively washed with dilute hydrochloric acid, sodium
bicarbonate solution and water, dried over anhydrous sodium sulfate and
evaporated to dryness under vacuum. There was thus obtained the
dipropionate of 2-hydroxymethylenedihydrotestosterone which was treated
with hydrogen, in methanol solution.
When the uptake of hydrogen ceased, the catalyst was filtered and the
solution was evaporated to dryness under vacuum. The residue was dissolved
in a mixture of benzene-hexane, transferred to a chromatographic column
with neutral alumina and the product was eluted with mixtures of benzenehexane, gradually increasing the proportion of benzene in the mixture.
Crystallization of the eluates from acetone-hexane yielded the propionate of
2α-methyldihydrotestosterone. | [Brand name]
Drolban (Lilly). | [Therapeutic Function]
Cancer chemotherapy | [Synthesis]
Drostanolone is prepared by this “one-pot-reaction”-step the conversion to the 1α-methyl-group is performed simultaneously with the cleavage of the protective group at the 17β-alcohol: 10.60 g Hydroxymethylene-precusor 2-Hydroxymethylene-androstan-17β-((tetrahydro-2H-pyran-2-yl)oxy)-3-one was nearly dissolved in 800 ml ethanol at 55°C. This
solution was hydrogenated in a pressure vessel (Parr reactor) with 6.00 g palladium on charcoal
(5%) at 4 bar and room temperature for 24 h. The mixture was filtered twice through paper and
the corresponding ethanol solution was evaporated, to yield 9.50 g colorless oil, still contains
traces of charcoal and ethanol. The crude product was purified by column chromatography on
silica gel by using hexane-ethyl acetate (8:2) as an eluent, to afford 5.45 g purified Drostanolone as
a colorless solid (69%) . MS (ESI+):
m/z = 304.96 (calculated MW: 304.47 g/mol)
Rf: 0.35, hexane/ethyl acetate 7:3, visualized by Seebach derivatization reagent.
1
H NMR(300 MHz, DMSO-d6) : δ 4.42 (d, 1 H, OH), 3.42 (m, 1H, HCHOH), 3.32 (s, 1H, CH),
2.37 (t, 1 H, CH), 1.99 (dd, 1 H, ), 1.84 (dd, 1H), 1.78 – 1.84 (m, 1H), 1.72 (m, 1H), 1.61 (m,
1H), 1.22-1.58 (m, 8H), 1.08 – 1.22 (m, 1H), 1.03 (s, 3H, CH3), 0.76-1.01 (m + d, 7H, 2α-CH3
+X), 0.65 – 0.72 (m, 1H), 0.64 (s, 3H, CH3). | [Mode of action]
It can promote protein synthesis and inhibit protein xenobiosis, reduce calcium and phosphorus excretion and alleviate bone marrow suppression, promote growth and development, promote tissue renewal and granulation, and reduce blood cholesterol, and have preventive and antagonistic effects on adrenocorticotropic hormone long-term use of adrenocorticotropic hypoplasia and protein anisotropy. | [References]
[1] SCH?NZER W, DONIKE M. Metabolism of anabolic steroids in man: synthesis and use of reference substances for identification of anabolic steroid metabolites[J]. Analytica Chimica Acta, 1993, 275: 23-48. DOI:10.1016/0003-2670(93)80274-O.
[2] KINTZ P, GHEDDAR L. Evidence of use of drostanolone, an anabolic steroid, at the time the subject committed a murder: Place of hair analysis[J]. Toxicologie Analytique et Clinique, 2021. DOI:10.1016/J.TOXAC.2021.05.002.
[3] LIU Y, LU J, YANG S, et al. New drostanolone metabolites in human urine by liquid chromatography time-of-flight tandem mass spectrometry and their application for doping control[J]. Steroids, 2016, 108: 61-67. DOI:10.1016/j.steroids.2016.01.013. |
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