72-63-9

Basic information

• Product Name: Metandienone
• Synonyms: 17-beta-hydroxy-17-alpha-methyl-androsta-4-dien-3-one;17-beta-Hydroxy-17-alpha-methylandrostra-1,4-dien-3-one;17-beta-hydroxy-17-methyl-androsta-4-dien-3-one;17beta-hydroxy-17-methyl-androsta-4-dien-3-one;17-hydroxy-17-methyl-4-dien-3-on(17-beta)-androsta-;17-hydroxy-17-methyl-4-dien-3-on(17beta)-androsta-;17-Hydroxy-17-methylandrosta-1,4-dien-3-one;17-Methyl-17-hydroxy-1,4-androstadi-en-3-one
• CAS NO: 72-63-9
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.43512
• EINECS: 200-787-2
• Product Categories: Biochemistry;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone;Finished Steroid and Hormone;API
• Mol File: 72-63-9.mol

Chemical Properties

• Melting Point: 165-166 °C
• Boiling Point: 381.66°C (rough estimate)
• Flash Point: -2℃
• Appearance: white to off-white crystalline powder
• Density: 1.0597 (rough estimate)
• Vapor Pressure: 1.87E-09mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: 2-8°C
• PKA: 15.12±0.60(Predicted)
• Merck: 5951
• BRN: 2056255
• CAS DataBase Reference: Metandienone(CAS DataBase Reference)
• NIST Chemistry Reference: Metandienone(72-63-9)
• EPA Substance Registry System: Metandienone(72-63-9)

Safety Data

• Hazard Codes: F,T
• Statements: 60-61-11-19-38
• Safety Statements: 53-45
• RIDADR: 3249
• WGK Germany: 3
• RTECS: BV8000000
• F: 8
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 72-63-9(Hazardous Substances Data)

Usage

Indications and Usage

Metandienone is a dehydrogenation derivative of methyltestosterone. Its protein assimilating effects are similar to those of testosterone propionate, but its androgen effects are slightly weaker and are about 1/100 those of the latter. This drug can promote protein synthesis, inhibit protein heterogeneity, maintain a positive nitrogen balance, improve appetite, aid muscle growth, and encourage weight gain. It can cause calcium and phosphorous deposition in bone tissue, promote bone mesenchymal cell formation, and increase bone calcification and growth. It can encourage tissue generation and granulation and speed up healing of wounds. It lowers blood cholesterol and improves fat metabolism. Metandienone is an androgen and anabolic hormone drug. It is suitable for people with insufficient protein synthesis and increased protein decomposition, such as patients with negative nitrogen balance caused by chronic wasting diseases, severe infections, trauma, and burns, as well as malignant tumors, osteoporosis, stunted children, dwarfism, fractures, less healing, and high cholesterol.

Drug Interactions

When Metandienone is used with oxyphenbutazone, the blood concentration of oxyphenbutazone may increase.

Adverse reactions

1. Metandienone’s adverse are identical to those of regular androgen and anabolic steroids. There may be nausea, vomiting, indigestion, diarrhea, and other digestive tract reactions. Long term, high dosage use may lead to bone weight, water-sodium retention, increased blood supply to skin, hypocalcemia, hyperosteogeny, etc. Women may experience slight virilism, with effects including acne, hirsuitism, lowered voice, clitoral hypertrophy, irregular menstruation, etc. 2. Metandienone’s side effects on the liver include jaundice and liver failure. There have been reports of liver cancer and benign hepatocellular adenoma tied to Metandianone use.

Contradictions

1. Do not use this drug if allergic. 2. Do not use if experiencing liver failure. 3. Do not use during pregnancy or if pregnancy may occur during treatment. 4. Do not use if experiencing prostate cancer, kidney disease, hypertension, or prostate hypertrophy.

Warnings and Precautions

1. Monitor liver functions while using Metandienone. 2. Dosage for elderly patients should be reduced accordingly. 3. Consume appropriate amounts of protein, sugar and vitamins during treatment to improve efficacy.

Chemical Properties

White Solid

Originator

Dianabol,Ciba,US,1960

Manufacturing Process

As described in US Patent 2,929,763, methandrostenolone may be made by a fermentation route. 2 g of sodium nitrate, 1 g of primary potassium orthophosphate, 0.5 g of magnesium sulfate heptahydrate, 0.5 g of potassium chloride, 50 g of glucose and 1 g of Difco yeast extract are dissolved in one liter of tap water, brought to pH 5 by addition of a sodium hydroxide solution and sterilized. The resulting nutrient solution is inoculated with 50 cc of a 4- day-old shaking culture of Didymella lycopersici and shaken for 48 hours at 27°C, whereby the culture becomes well developed. To two liters of a culture so prepared there is added under sterile conditions a solution of 500 mg of 17α-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-17αmethyl-testosterone is obtained in compact crystals. MP 163° to 164°C. An alternative synthetic route is described in US Patent 2,900,398 as follows. A suspension of 30 g of 17α-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. The mixture is refluxed for 24 hours with good stirring in an atmosphere of nitrogen, another 10 g of selenium dioxide being added after 10 hours. After some cooling, the suspension is filtered through some Hyflo and washed thoroughly with ethyl acetate. The resulting brown solution is evaporated in vacuo and the residue dissolved in ethyl acetate. 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-dehydro17α-methyl-testosterone which melts at 163° to 164°C.

Therapeutic Function

Androgen, Anabolic

InChI:InChI=1/C20H28O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h6,9,12,15-17,22H,4-5,7-8,10-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1

Synthetic route

methyl bromide (74-83-9) + Androsta-1,4-diene-3,17-dione (897-06-3) → metandienone (72-63-9)

Conditions	Yield
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃; Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃;	94.6%
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃; Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃;	94.6%
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃; Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃; Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3;	93.8%

methylene chloride (74-87-3) + Androsta-1,4-diene-3,17-dione (897-06-3) → metandienone (72-63-9)

Conditions	Yield
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃;	92.5%
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃;	92.5%
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃; Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3;	92.5%

Androsta-1,4-diene-3,17-dione (897-06-3) + methyl iodide (74-88-4) → metandienone (72-63-9)

Conditions	Yield
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃;	90.8%
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃;	90.8%
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃; Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃; Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3;	90.8%

17-methyltestosterone (58-18-4) → metandienone (72-63-9)

Conditions	Yield
With tert-butyldimethylsilyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 0 - 20℃; for 48h;	78%
With selenium(IV) oxide
mit Hilfe von Didymella lycopersici;

monomethyl oxalyl chloride (5781-53-3) + metandienone (72-63-9) → methyl ((8R,9S,10R,13S,14S,17S)-10,13,17-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl) oxalate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	95%

metandienone (72-63-9) → (8S,9S,10R,13S,14S)-10,13,17-trimethyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-3(10H)-one (64760-67-4)

Conditions	Yield
With Amberlyst-15 In dichloromethane at 20℃; for 6h;	90%

metandienone (72-63-9) → 15α,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one + 6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one (33526-41-9)

Conditions	Yield
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 264h; Enzymatic reaction;	A 83% B 9%

di-tert-butyl-diazodicarboxylate (870-50-8) + metandienone (72-63-9) → C30H46N2O6

Conditions	Yield
With cerium(III) chloride; tetrabutyl-ammonium chloride In acetonitrile for 48h; Inert atmosphere; Irradiation; diastereoselective reaction;	71%

metandienone (72-63-9) → 17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one (77702-25-1)

Conditions	Yield
With hydrogenchloride at 60℃; for 0.5h;	60%
With hydrogenchloride In methanol; water for 16h; Reflux;

metandienone (72-63-9) → androsta-3,5-dien-17β-ol, 17-methyl-

Conditions	Yield
Stage #1: metandienone With C19H26ClIrN3O(1+)*Cl(1-) In water; acetonitrile at 80℃; for 0.166667h; Green chemistry; Stage #2: With formic acid In water; acetonitrile at 80℃; for 4h; Green chemistry;	35%

metandienone (72-63-9) → 17-methyltestosterone (58-18-4)

Conditions	Yield
With thallium(III) nitrate trihydrate In diethylene glycol dimethyl ether for 24h; Ambient temperature;	34%

metandienone (72-63-9) + UDP-glucuronic acid (2616-64-0) → 17β-methyl-5β-androst-1-ene-17α-ol-3α-O-glucuronide (1062581-61-6) + 17α-methyl-5β-androstane-17β-ol-3α-O-glucuronide

Conditions	Yield
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4;	A 25% B n/a

metandienone (72-63-9) → 1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol + (3aα,8aα,8bβ)-dodecahydro-5aβ,6α-dimethyl-6β-hydroxy-2'-methyl-as-indacene-3(R)-spiro-(2',5'-cyclohexadienone)

Conditions	Yield
With axenic culture of strain T76 Scenedesmus quadricauda	A 11% B 21%
With axenic culture of strain T76 of Scenedesmus quadricauda	A 11% B 21%

metandienone (72-63-9) → anti-17α-Methyl-17β-hydroxy-Δ1,4-androstadien-3-N-chlorimin

Conditions	Yield
(i) MeNH2, MeOH, (ii) aq. Ca(OCl)2, NH3, NH4Cl; Multistep reaction;

pyridine (110-86-1) + metandienone (72-63-9) → methandienone 17β-sulfate pyridinium salt (143579-41-3)

Conditions	Yield
With chlorosulfonic acid 1.) -5 deg C, 2.) RT, 3 h; Yield given. Multistep reaction;

metandienone (72-63-9) → metanedienone-17-sulfate (119888-55-0)

Conditions	Yield
With sulfur trioxide pyridine complex In N,N-dimethyl-formamide for 12h; Ambient temperature;	3.8 g

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide (24589-78-4) + metandienone (72-63-9) → (8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-3,17-bis-trimethylsilanyloxy-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclopenta[a]phenanthrene (136693-32-8)

Conditions	Yield
With ammonium iodide In ethyl acetate for 1h; Heating;	97 % Chromat.
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h;
With ammonium iodide; ethanethiol In acetonitrile at 80℃; for 0.5h;

metandienone (72-63-9) → 3,5-Dioxo-17β-hydroxy-17α-methyl-10(5->4)-abeo-Δ1-androsten (13712-20-4)

Conditions	Yield
(i) PhCO3H, CHCl3, (ii) (UV-irradiation), dioxane; Multistep reaction;

methanol (67-56-1) + metandienone (72-63-9) → 1-Hydroxy-4.17.17-trimethyl-7.8.9.11.12.15.16.17-octahydro-6H-cyclopentaphenanthren (94761-63-4)

Conditions	Yield
With hydrogenchloride

methanol (67-56-1) + metandienone (72-63-9) → 13-Chlor-1-methoxy-4.17.17-trimethyl-13ξ-gonatrien-(A) (96671-98-6)

Conditions	Yield
With hydrogenchloride

methanol (67-56-1) + metandienone (72-63-9) → 17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one (77702-25-1)

Conditions	Yield
With hydrogenchloride

metandienone (72-63-9) → 17β-Hydroxy-17α-methyl-Δ1.5-androstadien-3-on (2694-97-5)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide

metandienone (72-63-9) → 1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol + (3S,3aS,5aS,6R,6aR,11aS,11bS)-3,6-Dihydroxy-3,3a,6-trimethyl-1,2,3,3a,4,5,5a,6,6a,7,10,11,11a,11b-tetradecahydro-indeno[5,4-f]azulen-8-one + C20H28O2 + 5α,17β-dihydroxy-17α-methyl-androst-1-en-3-one

Conditions	Yield
With water In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given;

metandienone (72-63-9) → 1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol + C20H28O2 + 5β,17β-dihydroxy-17α-methyl-androst-1-en-3-one + 5α,17β-dihydroxy-17α-methyl-androst-1-en-3-one

Conditions	Yield
In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given;
With water In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given;

metandienone (72-63-9) → 17β-hydroxy-17α-methylandrost-4-en-3β-ol (571-03-9) + (3R,8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 2h;

metandienone (72-63-9) → 17α-17-hydroxy-17-methylandrosta-1,4-dien-3-one (33526-40-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature 2: H2O / 24 h View Scheme

metandienone (72-63-9) → 17-epimetandienone,bis-TMS

Conditions	Yield
Multi-step reaction with 4 steps 1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature 2: H2O / 24 h 3: trimethylsilylimidazole / 0.17 h / 60 °C 4: trimethyliodosilane / 0.25 h / 60 °C View Scheme

metandienone (72-63-9) → (8R,9S,10R,13S,14S,17R)-10,13,17-Trimethyl-17-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one (73024-97-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature 2: H2O / 24 h 3: trimethylsilylimidazole / 0.17 h / 60 °C View Scheme

metandienone (72-63-9) → 17α-Methyl-androsta-1,5-dien-3β,17β-diol (2694-98-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOtBu / dimethylsulfoxide 2: NaBH4 / methanol View Scheme

Upstream product

• 74-87-3 methylene chloride 
• 897-06-3 androsta-1,4-diene-3,17-dione 
• 58-18-4 17-methyltestosterone 
• 897-06-3 Androsta-1,4-diene-3,17-dione 
• 74-83-9 methyl bromide 
• 74-88-4 methyl iodide 

Downstream Products

• 58-18-4 17-methyltestosterone 
• 77702-25-1 17,17-dimethyl-18-norandrosta-1,4,13⁽¹⁴⁾-trien-3-one 
• 2694-97-5 17β-Hydroxy-17α-methyl-Δ^1.5-androstadien-3-on 
• 571-03-9 17α-methyl-4-androstene-3β,17β-diol 
• 33526-41-9 6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one 
• 2694-98-6 17α-Methyl-androsta-1,5-dien-3β,17β-diol 
• 136286-32-3 6β,12β,17β-trihydroxy-17α-methylandrost-1,4-dien-3-one 
• 1610690-42-0 6β,15α,17β-trihydroxy-17α-methylandrost-1,4-dien-3-one 
• 25356-68-7 11α-hydroxymethandrostenolone 
• 642485-68-5 7β,17β,-dihydroxy-17α-methylandrost-1,4-dien-3-one 
• 35937-36-1 15β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one 
• 110745-95-4 17β-hydroxy-17α-methylandrost-1,4-dien-3,11-dione 
• 59701-14-3 17β-hydroxy-17α-methylandrost-1,4-dien-3,6-dione 
• 22204-44-0 11β,17β-dhydroxy-17α-methylandrost-1,4-dien-3-one 

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Preparation method of metandienone

The invention provides a preparation method of metandienone. The method comprises the following steps: adopting 1,4-androstadienedione, namely IDD, as a raw material; introducing alpha-CH3 and beta-OHto 17th site in the presence of methyl-Grignard-reagent, an organic solvent and acid to obtain the metandienone. Compared with a traditional method taking diosgenin as a raw material, a method for preparing the metandienone by taking the IDD as the raw material, disclosed by the invention, has the advantages that sources of raw materials are wide, a process is economic and environmentally-friendly, and the production cost is greatly reduced; besides, the method disclosed by the invention, compared with the traditions method, has the characteristics of short synthesis route, simple and environmentally-friendly process, high product yield and good quality; calculated by the current price of the raw materials, the cost of the raw materials for production is reduced by 40 to 45 percent.

Method for preparing metandienone product

The invention provides a method for preparing a metandienone product. The method comprises the following steps of: crystallizing and separating deodorized distillates in production of soybean oil to obtain phytosterol, carrying out microbial fermentation on the phytosterol by adopting a nutritional culture medium and one or more microorganism bacteria to obtain 1,4-androstadienedione, i.e. IDD, then preparing metandienone in the presence of methylmagnesium halide, an organic solvent and acid by using the IDD as a raw material, and refining the metandienone to obtain the metandienone product. The metandienone is prepared by adopting the IDD as the raw material; and compared with a traditional method adopting diosgenin as the raw material, the method of the invention has the advantages thatthe source of the raw materials is wide, the process is economical and environmentally friendly, and the production cost is greatly reduced. Compared with a traditional production method, the method of the invention has the advantages of short synthetic route, simple and environment-friendly process, high product yield, and good quality; and by calculating at the price of the raw material at present, the cost of the production raw material can be reduced by 40 to 45 percent.

Method for preparing metandienone

The invention provides a method for preparing metandienone, the method comprises firstly using a nutrient medium and one or more microbial strains, performing microbial fermentation on phytosterol toprepare 1,4-androstenedione, namely IDD, then using the IDD as the raw material, introducing alpha-CH3 and beta-OH into a 17 site with the existence of methyl magnesium halide, an organic solvent andan acid, and preparing the metandienone. The method uses the IDD as the raw material to prepare the metandienone, compared with the traditional method taking diosgenin as the raw material, the sourceof the raw material is wide, the process is economical and environmentally friendly, and the production cost is greatly reduced. Compared with the traditional production method, the synthesis route isshort, the process is simple, convenient and environmentally friendly, the yield of a product is high, the quality is high, and the cost of the raw material for production is reduced by 40-45% according to the current price of the raw material.

Preparation method of metandienone product

The invention provides a preparation method of a metandienone product. The preparation method comprises the following steps that 1,4-androstenedione, namely IDD, is adopted as a raw material, in the presence of methylmagnesium chloride, an organic solvent and acid, alpha-CH3 and beta-OH are introduced at the 17 position, and metandienone is prepared; and then the obtained metandienone is heated byactivated carbon in acetone or lower alcohol below C4 for reflow discoloration and is recrystallized, and the metandienone product is obtained. According to the preparation method, the IDD serves asthe raw material to prepare the metandienone, compared with a traditional method adopting diosgenin as a raw material, the raw material source is wide, a process is economic and environmentally friendly, and the production cost is significantly lowered. Compared with a traditional production method, according to the preparation method, a synthesis route is short, the process is easy, convenient and environmentally friendly, the product yield is high, the quality is good, and the production raw material cost is lowered by 40-45% by calculating through the current raw material price.

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