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72-63-9 Usage

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.

Uses

Anabolic steroid. Androgen. Controlled substance.

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.

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.

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.

Chemical Properties

White Solid
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

72-63-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Methandrostenolone

1.2 Other means of identification

Product number -
Other names Metandienone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:72-63-9 SDS

72-63-9Synthetic 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
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;
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;
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

72-63-9Downstream Products