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| Name |
Metandienone |
EINECS | 200-787-2 |
| CAS No. | 72-63-9 | Density | 1.12 g/cm3 |
| PSA | 37.30000 | LogP | 4.04530 |
| 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 |
|
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; |
Article Data | 34 |
Metandienone Synthetic route
| 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% |
| 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% |
| 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% |
| 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; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With Amberlyst-15 In dichloromethane at 20℃; for 6h; | 90% |
- 72-63-9
metandienone
B
- 33526-41-9
6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one
| Conditions | Yield |
|---|---|
| With Penicillium notatum KCH 904 In water; acetone at 27℃; for 264h; Enzymatic reaction; | A 83% B 9% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride at 60℃; for 0.5h; | 60% |
| With hydrogenchloride In methanol; water for 16h; Reflux; |
- 72-63-9
metandienone
| 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 Consensus Reports
Metandienone Standards and Recommendations
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. |