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72-63-9

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Basic Information
CAS No.: 72-63-9
Name: Androsta-1,4-dien-3-one,17-hydroxy-17-methyl-, (17b)-
Molecular Structure:
Molecular Structure of 72-63-9 (Androsta-1,4-dien-3-one,17-hydroxy-17-methyl-, (17b)-)
Formula: C20H28O2
Molecular Weight: 300.44
Synonyms: Androsta-1,4-dien-3-one,17b-hydroxy-17-methyl- (8CI);1,2-Dehydro-17-methyltestosterone;1-Dehydro-17a-methyltestosterone;17-Methylandrosta-1,4-dien-17b-ol-3-one;17a-Methyl-1-dehydrotestosterone;17a-Methyl-17b-hydroxyandrost-1,4-dien-3-one;17a-Methylandrosta-1,4-dien-17b-ol-3-one;17b-Hydroxy-17-methylandrosta-1,4-dien-3-one;17b-Hydroxy-17a-methylandrosta-1,4-dien-3-one;Abirol;Compound 17309;Crein;Danabol;Dianabol;Dianabole;MA;Metanabol;Metandienon;Metandienonum;Metandrostenolon;Metandrostenolone;Methandon;Methandrolone;Methandrostenolone;NSC 51180;Naposim;Nerobolettes;Protobolin;Stenolon;Stenolone;D1-17a-Methyltestosterone;
EINECS: 200-787-2
Density: 1.12 g/cm3
Melting Point: 165-166 °C
Boiling Point: 436.5 °C at 760 mmHg
Flash Point: 186.2 °C
Solubility: practically insoluble in water
Appearance: white to off-white crystalline powder
Hazard Symbols: F,T
Risk Codes: 60-61-11-19-38
Safety: 53-45
Transport Information: UN 3249
PSA: 37.30000
LogP: 4.04530
Synthetic route
74-83-9

methyl bromide

897-06-3

Androsta-1,4-diene-3,17-dione

72-63-9

metandienone

Conditions
ConditionsYield
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%
74-87-3

methylene chloride

897-06-3

Androsta-1,4-diene-3,17-dione

72-63-9

metandienone

Conditions
ConditionsYield
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%
897-06-3

Androsta-1,4-diene-3,17-dione

74-88-4

methyl iodide

72-63-9

metandienone

Conditions
ConditionsYield
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%
58-18-4

17-methyltestosterone

72-63-9

metandienone

Conditions
ConditionsYield
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;
5781-53-3

monomethyl oxalyl chloride

72-63-9

metandienone

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
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;95%
72-63-9

metandienone

64760-67-4

(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

Conditions
ConditionsYield
With Amberlyst-15 In dichloromethane at 20℃; for 6h;90%
72-63-9

metandienone

A

15α,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one

B

33526-41-9

6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one

Conditions
ConditionsYield
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 264h; Enzymatic reaction;A 83%
B 9%
870-50-8

di-tert-butyl-diazodicarboxylate

72-63-9

metandienone

C30H46N2O6

Conditions
ConditionsYield
With cerium(III) chloride; tetrabutyl-ammonium chloride In acetonitrile for 48h; Inert atmosphere; Irradiation; diastereoselective reaction;71%
72-63-9

metandienone

77702-25-1

17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one

Conditions
ConditionsYield
With hydrogenchloride at 60℃; for 0.5h;60%
With hydrogenchloride In methanol; water for 16h; Reflux;
72-63-9

metandienone

androsta-3,5-dien-17β-ol, 17-methyl-

Conditions
ConditionsYield
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%
72-63-9

metandienone

58-18-4

17-methyltestosterone

Conditions
ConditionsYield
With thallium(III) nitrate trihydrate In diethylene glycol dimethyl ether for 24h; Ambient temperature;34%
72-63-9

metandienone

2616-64-0

UDP-glucuronic acid

A

1062581-61-6

17β-methyl-5β-androst-1-ene-17α-ol-3α-O-glucuronide

B

17α-methyl-5β-androstane-17β-ol-3α-O-glucuronide

Conditions
ConditionsYield
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4;A 25%
B n/a
72-63-9

metandienone

A

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

B

(3aα,8aα,8bβ)-dodecahydro-5aβ,6α-dimethyl-6β-hydroxy-2'-methyl-as-indacene-3(R)-spiro-(2',5'-cyclohexadienone)

Conditions
ConditionsYield
With axenic culture of strain T76 Scenedesmus quadricaudaA 11%
B 21%
With axenic culture of strain T76 of Scenedesmus quadricaudaA 11%
B 21%
72-63-9

metandienone

anti-17α-Methyl-17β-hydroxy-Δ1,4-androstadien-3-N-chlorimin

Conditions
ConditionsYield
(i) MeNH2, MeOH, (ii) aq. Ca(OCl)2, NH3, NH4Cl; Multistep reaction;
110-86-1

pyridine

72-63-9

metandienone

143579-41-3

methandienone 17β-sulfate pyridinium salt

Conditions
ConditionsYield
With chlorosulfonic acid 1.) -5 deg C, 2.) RT, 3 h; Yield given. Multistep reaction;
72-63-9

metandienone

119888-55-0

metanedienone-17-sulfate

Conditions
ConditionsYield
With sulfur trioxide pyridine complex In N,N-dimethyl-formamide for 12h; Ambient temperature;3.8 g
24589-78-4

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

72-63-9

metandienone

136693-32-8

(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

Conditions
ConditionsYield
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;
72-63-9

metandienone

13712-20-4

3,5-Dioxo-17β-hydroxy-17α-methyl-10(5->4)-abeo-Δ1-androsten

Conditions
ConditionsYield
(i) PhCO3H, CHCl3, (ii) (UV-irradiation), dioxane; Multistep reaction;
67-56-1

methanol

72-63-9

metandienone

94761-63-4

1-Hydroxy-4.17.17-trimethyl-7.8.9.11.12.15.16.17-octahydro-6H-cyclopentaphenanthren

Conditions
ConditionsYield
With hydrogenchloride
67-56-1

methanol

72-63-9

metandienone

96671-98-6

13-Chlor-1-methoxy-4.17.17-trimethyl-13ξ-gonatrien-(A)

Conditions
ConditionsYield
With hydrogenchloride
67-56-1

methanol

72-63-9

metandienone

77702-25-1

17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one

Conditions
ConditionsYield
With hydrogenchloride
72-63-9

metandienone

2694-97-5

17β-Hydroxy-17α-methyl-Δ1.5-androstadien-3-on

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide
72-63-9

metandienone

A

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

B

(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

C

C20H28O2

D

5α,17β-dihydroxy-17α-methyl-androst-1-en-3-one

Conditions
ConditionsYield
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;
72-63-9

metandienone

A

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

B

C20H28O2

C

5β,17β-dihydroxy-17α-methyl-androst-1-en-3-one

D

5α,17β-dihydroxy-17α-methyl-androst-1-en-3-one

Conditions
ConditionsYield
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;
72-63-9

metandienone

A

571-03-9

17β-hydroxy-17α-methylandrost-4-en-3β-ol

B

(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
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 2h;
72-63-9

metandienone

33526-40-8

17α-17-hydroxy-17-methylandrosta-1,4-dien-3-one

Conditions
ConditionsYield
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
72-63-9

metandienone

17-epimetandienone,bis-TMS

Conditions
ConditionsYield
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
72-63-9

metandienone

73024-97-2

(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

Conditions
ConditionsYield
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
72-63-9

metandienone

2694-98-6

17α-Methyl-androsta-1,5-dien-3β,17β-diol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOtBu / dimethylsulfoxide
2: NaBH4 / methanol
View Scheme
Raw Materials
58-18-4
Downstream Products
58-18-4
2694-98-6
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Consensus Reports

EPA Genetic Toxicology Program.

Standards and Recommendations

ASSAY: 97.0 - 103.0% 
OPTICAL ROTATION: +7° ~ +11° 
LOSS ON DRYING: 0.5% max

Specification

The IUPAC name of Metandienone is (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one. With the CAS registry number 72-63-9, it is also named as 1,2-Dehydro-17-methyltestosterone. The product's categories are biochemistry; hydroxyketosteroids; steroids. It is white to off-white crystalline powder which is almost insoluble in water, soluble in alcohol and chloroform, and slightly soluble in ether. Additionally, Metandienone can be obtained by Sisal sapogenin. When heated to decomposition it emits acrid smoke and irritating fumes.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.04; (4)ACD/LogD (pH 7.4): 4.04; (5)ACD/BCF (pH 5.5): 691.04; (6)ACD/BCF (pH 7.4): 691.04; (7)ACD/KOC (pH 5.5): 3750.76; (8)ACD/KOC (pH 7.4): 3750.76; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.572; (13)Molar Refractivity: 87.68 cm3; (14)Molar Volume: 266.3 cm3; (15)Polarizability: 34.76×10-24 cm3; (16)Surface Tension: 44.9 dyne/cm; (17)Enthalpy of Vaporization: 80 kJ/mol; (18)Vapour Pressure: 1.87E-09 mmHg at 25°C; (19)Tautomer Count: 3; (20)Exact Mass: 300.20893; (21)MonoIsotopic Mass: 300.20893; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 22; (24)Complexity: 589.

Uses of Metandienone: It is androgen, assimilation hormone metandienone which is used for treatment of chronic wasting disease, stunted children, osteoporosis, hyperlipidemia and negative nitrogen balance which is cauded by severe infection, burns, etc.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C\1\C=C/[C@]4(/C(=C/1)CC[C@@H]3[C@@H]4CC[C@]2([C@H]3CC[C@@]2(O)C)C)C
2. 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

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intraperitoneal 425mg/kg (425mg/kg)   Pharmaceutical Chemistry Journal Vol. 20, Pg. 143, 1986.
rat LD50 oral > 1gm/kg (1000mg/kg)   Drugs in Japan Vol. 6, Pg. 821, 1982.