メチルテストステロン(58-18-4)

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メチルテストステロン 製品概要
化学名:メチルテストステロン
英語化学名:17-Methyltestosterone
别名:mtmucorettes;Neo-Hombreol-M;Neo-Homobreol (M);NSC-9701;Nu-man;Oraviron;Orchisterone-M;Oreton Methyl
CAS番号:58-18-4
分子式:C20H30O2
分子量:302.46
EINECS:200-366-3
カテゴリ情報:Inhibitors;testosterone;Hormone Drugs;API;Steroid and Hormone;API's;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;58-18-4
Mol File:58-18-4.mol
メチルテストステロン
メチルテストステロン 物理性質
融点 162-168 °C(lit.)
比旋光度 79 º (c=1, alcohol)
沸点 383.47°C (rough estimate)
比重(密度) 1.0434 (rough estimate)
屈折率 1.4800 (estimate)
闪点 5 °C
貯蔵温度 2-8°C
溶解性H2O: ≤0.5 mg/mL
外見 solid (photosensitive)
酸解離定数(Pka)15.13±0.60(Predicted)
white
水溶解度 33.88mg/L(25 ºC)
Merck 13,6148
BRN 2057425
InChIKeyGCKMFJBGXUYNAG-HLXURNFRSA-N
CAS データベース58-18-4(CAS DataBase Reference)
NISTの化学物質情報17(Alpha)-methyl-delta4-androsten-17-(beta)-ol-3-one(58-18-4)
EPAの化学物質情報Methyltestosterone (58-18-4)
安全性情報
主な危険性 T,Xn,F,Xi
Rフレーズ 45-63-22-20-19-11-61-60-36/37/38-38-10
Sフレーズ 53-36/37-45-24/25-22
RIDADR 3249
WGK Germany 3
RTECS 番号BV8400000
国連危険物分類 6.1(b)
容器等級 III
HSコード 29372900
有毒物質データの58-18-4(Hazardous Substances Data)
毒性man,TDLo,oral,39mg/kg/33W-I (39mg/kg),LIVER: "JAUNDICE, CHOLESTATIC",American Journal of Gastroenterology. Vol. 82, Pg. 461, 1987.
MSDS Information
ProviderLanguage
17-Methyltestosterone English
SigmaAldrich English
ACROS English
メチルテストステロン Usage And Synthesis
外観白色~わずかにうすい黄色、結晶性粉末~粉末
溶解性エタノール(95)及びメタノールに溶けやすく、アセトンにやや溶けやすく、水にほとんど溶けない。
用途薬理研究用。
用途合成テストステロンです。黄 体ホルモン依存性の腫瘍増殖抑制作用を示し ます。
効能男性ホルモン補充薬, アンドロゲン受容体作動薬
使用上の注意アルゴン封入
説明Methyltestosterone is a synthetic analog of testosterone that possesses all of the properties of testosterone, exhibiting stimulatory action on the development of male sex organs and secondary sex characteristics, although it is not degraded by enzymes in the gastrointestinal tract, and therefore it can only be taken orally
化学的特性white to slightly yellowish-white crystalline
OriginatorMetandren ,Ciba,US,1941
使用It is used for the same indications as testosterone for sexual underdevelopment, functional problems of the reproductive system, and the vascular nerve disorders associated with climacteric problems in men. It is also used for dysfunctional uterine bleeding in premenopausal and menopausal women as well as for breast and ovarian cancer.
使用Androgen. It has been used as an androgenic agent. Controlled substance (anabolic steroid).
定義ChEBI: A 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position.
Manufacturing Process0.6 g of 17-Methyl-?5,6-androstenediol-(3,17) is heated under reflux cooling during 20 hours in 50 cm3 of benzene and 12 cm3 of acetone with 3 g of tertiary chloromagnesium butylate, which may be prepared by conversion of acetone with methyl magnesium chloride. The magnesium is then removed by shaking out with dilute H2SO4; the benzene layer is washed with water, dried with sodium sulfate and then evaporated to dryness. Methyltestosterone (MP 160° to 162°C) is obtained in a yield of more than 75% of the theory, according to US Patent 2,384,335.
brand nameAndroid (Valeant);Metandren (Novartis); Oreton (Schering); Testred (Valeant); Virilon (Star).
Therapeutic FunctionAndrogen
薬物動態学The synthesis of 17α-methyltestosterone made available a compound that was orally active in daily doses between 10 and 50 mg, which is equivalent to a 400 mg oral dose of testosterone. The presence of a 17α alkyl group reduces susceptibility to hepatic oxidative metabolism, thereby increasing oral bioavailability by slowing metabolism. Following oral administration, methyltestosterone is well absorbed from the gastrointestinal tract, with a half-life of approximately 3 hours. This drug has the androgenic and anabolic activities of testosterone. Although orally active, it is more effective when administered sublingually. The alkylated oral androgens should be viewed as potentially hepatotoxic and should not be used.
安全性プロファイルPoison by intraperitoneal route. Moderately toxic by ingestion. Human teratogenic effects by ingestion: developmental abnormalities of the urogenital system. Experimental teratogenic and reproductive effects. Human systemic effects: cholestatic jaundce, weight loss or decreased weight gain. Questionable human carcinogen producing liver tumors. A synthetic androgenic steroid. When heated to decomposition it emits acrid smoke and irritating fumes.
合成Methyltestosterone, 17|?-hydroxy-17|á-methylandrost-4-en-3-one (29.1.7), is also synthesized from androstenolone by reacting it with methylmagnesiumiodide, forming the corresponding tertiary alcohol (29.1.6), and subsequent oxidation of the hydroxyl group at C3 to a ketone using chromium (VI) oxide. Simultaneous isomerization of the double bond takes place under the reaction conditions, giving the desired methyltestosterone (29.1.7).

Synthesis_58-18-4

純化方法This anabolic steroid is crystallised from hexane or hexane/*benzene. It has E1cm 1% 495-530 at 241nm (EtOH). The colour reaction with 2,4-dinitrophenyl hydrazine is used for assaying it. [Gornall & Macdonald J Biol Chem 201 279 1953.] In another colour reaction the sterone (1mg) in acetic acid (0.2ml) + 88% H3PO4 (2mL) is allowed to stand for 1hour when it becames fluorescent. After 1hour it is diluted with acetic acid (~3mL) and provides a strong yellow fluorescence with the intensity of 50-100 times that of estrone. [Stuart & Stuckey J Pharm Pharmacol 1 130 1949, Openauer Rec Trav Chim Pays-Bas 56 137 137, Beilstein 8 IV 1010.]
Tags:58-18-4