Product Name

This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.
  • Name

    Metandienone

  • EINECS 200-787-2
  • CAS No. 72-63-9
  • Article Data34
  • CAS DataBase
  • Density 1.12 g/cm3
  • Solubility practically insoluble in water
  • Melting Point 165-166 °C
  • Formula C20H28O2
  • Boiling Point 436.5 °C at 760 mmHg
  • Molecular Weight 300.441
  • Flash Point 186.2 °C
  • Transport Information UN 3249
  • Appearance white to off-white crystalline powder
  • Safety 53-45
  • Risk Codes 60-61-11-19-38
  • Molecular Structure Molecular Structure of 72-63-9 (Metandienone)
  • Hazard Symbols F,T
  • 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;
  • PSA 37.30000
  • LogP 4.04530

Synthetic route

methyl bromide
74-83-9

methyl bromide

Androsta-1,4-diene-3,17-dione
897-06-3

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

metandienone
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%
methylene chloride
74-87-3

methylene chloride

Androsta-1,4-diene-3,17-dione
897-06-3

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

metandienone
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%
Androsta-1,4-diene-3,17-dione
897-06-3

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

methyl iodide
74-88-4

methyl iodide

metandienone
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%
17-methyltestosterone
58-18-4

17-methyltestosterone

metandienone
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;
monomethyl oxalyl chloride
5781-53-3

monomethyl oxalyl chloride

metandienone
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

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%
metandienone
72-63-9

metandienone

(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

(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%
metandienone
72-63-9

metandienone

A

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

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

B

6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one
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%
di-tert-butyl-diazodicarboxylate
870-50-8

di-tert-butyl-diazodicarboxylate

metandienone
72-63-9

metandienone

C30H46N2O6

C30H46N2O6

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

metandienone

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

metandienone

androsta-3,5-dien-17β-ol, 17-methyl-

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%
metandienone
72-63-9

metandienone

17-methyltestosterone
58-18-4

17-methyltestosterone

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

metandienone

UDP-glucuronic acid
2616-64-0

UDP-glucuronic acid

A

17β-methyl-5β-androst-1-ene-17α-ol-3α-O-glucuronide
1062581-61-6

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

B

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

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
...Expand
metandienone
72-63-9

metandienone

A

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

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)

(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%
metandienone
72-63-9

metandienone

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

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;
pyridine
110-86-1

pyridine

metandienone
72-63-9

metandienone

methandienone 17β-sulfate pyridinium salt
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;
metandienone
72-63-9

metandienone

metanedienone-17-sulfate
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
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide
24589-78-4

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

metandienone
72-63-9

metandienone

(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

(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;
metandienone
72-63-9

metandienone

3,5-Dioxo-17β-hydroxy-17α-methyl-10(5->4)-abeo-Δ1-androsten
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;
methanol
67-56-1

methanol

metandienone
72-63-9

metandienone

1-Hydroxy-4.17.17-trimethyl-7.8.9.11.12.15.16.17-octahydro-6H-cyclopentaphenanthren
94761-63-4

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

Conditions
ConditionsYield
With hydrogenchloride
methanol
67-56-1

methanol

metandienone
72-63-9

metandienone

13-Chlor-1-methoxy-4.17.17-trimethyl-13ξ-gonatrien-(A)
96671-98-6

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

Conditions
ConditionsYield
With hydrogenchloride
methanol
67-56-1

methanol

metandienone
72-63-9

metandienone

17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one
77702-25-1

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

Conditions
ConditionsYield
With hydrogenchloride
metandienone
72-63-9

metandienone

17β-Hydroxy-17α-methyl-Δ1.5-androstadien-3-on
2694-97-5

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

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

metandienone

A

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

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

(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

C20H28O2

D

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

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;
...Expand
metandienone
72-63-9

metandienone

A

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

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

B

C20H28O2

C20H28O2

C

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

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

D

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

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;
...Expand
metandienone
72-63-9

metandienone

A

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

(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;
metandienone
72-63-9

metandienone

17α-17-hydroxy-17-methylandrosta-1,4-dien-3-one
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
metandienone
72-63-9

metandienone

17-epimetandienone,bis-TMS

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
metandienone
72-63-9

metandienone

(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

(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
metandienone
72-63-9

metandienone

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

Metandienone Consensus Reports

EPA Genetic Toxicology Program.

Metandienone Standards and Recommendations

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

Metandienone 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.

Related Products

Hot Products

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View