153-00-4

Basic information

• Product Name: Metenolone
• Synonyms: METHENOLONE;metenolone;1(5-ALPHA)-ANDROSTEN-1-BETA-METHYL-17-BETA-OL-3-ONE;1,5ALPHA-ANDROSTEN-1-METHYL-17BETA-OL-3-ONE;17beta-hydroxy-1-methyl-5alpha-androst-1-en-3-one;MethenoloneAcetate434-05-9/Base;17b-Hydroxy-1-methyl-5a-androst-1-en-3-one;1-Methyl-D1-androsten-17b-ol-3-one
• CAS NO: 153-00-4
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.45
• EINECS: 205-812-0
• Product Categories: Steroids;Steroid and Hormone;Finished Steroid and Hormone;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 153-00-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 149.5-152°; mp 160-161° (Popper)
• Boiling Point: 430.381 °C at 760 mmHg
• Flash Point: 183.597 °C
• Appearance: /
• Density: 1.084 g/cm³
• Vapor Pressure: 3.26E-09mmHg at 25°C
• Refractive Index: 1.542
• PKA: 15.08±0.70(Predicted)
• CAS DataBase Reference: Metenolone(CAS DataBase Reference)
• NIST Chemistry Reference: Metenolone(153-00-4)
• EPA Substance Registry System: Metenolone(153-00-4)

Safety Data

• Hazardous Substances Data: 153-00-4(Hazardous Substances Data)

Usage

Originator

Primobolan ,Schering ,W. Germany,1961

Uses

Methenolone is an anabolic steroid. This is a controlled substance.

Manufacturing Process

8.42 ml of methyl iodide are slowly added dropwise at room temperature with stirring in a nitrogen atmosphere to 3.067 g of magnesium turnings and 107 ml of absolute ether. After about 30 minutes, 185 ml of absolute tetrahydrofuran are slowly introduced and then liquid is distilled off until a boiling point of 62°C is reached. After cooling to room temperature, 613 mg of cuprous chloride are added and then 10 g of ?1,4,6-androstatrien-17β-ol-3- one-17-acetate in 110 ml of tetrahydrofuran slowly introduced. After 30 minutes reaction time, the whole is cooled to 0C, the excess of Grignard reagent decomposed with saturated ammonium chloride solution, the product diluted with ether and the aqueous phase separated. The ethereal phase is washed consecutively with aqueous sodium thiosulfate solution, saturated ammonium chloride solution and water. It is dried over sodium sulfate and evaporated to dryness under vacuum. The residue is dissolved in 40 ml of pyridine and 20 ml of acetic anhydride and the solution kept for 16 hours at room temperature. It is then stirred into ice water and the precipitate filtered with suction, dried and recrystallized from isopropyl ether. 1α-Methyl-?4,6- androstadien-17β-ol-3-one-17-acetate is obtained. MP 156°C to 157°C; [α]D25 = -33.8° (in CHCl3; c = 0.9). Yield 65-70% of the theoretical.4.67 g of 1α-methyl-?4,6-androstadien-17β-ol-3-one-17-acetate are dissolved in 273 ml of methanol and, after the addition of 350 mg of 10% palladium on calcium carbonate catalyst, hydrogenated until 1 mol equivalent of hydrogen has been taken up. After filtering off the catalyst, the solution is treated with 150 ml of 2N-hydrochloric acid and evaporated under vacuum to about 1/3 of the volume. The whole is then diluted with water and extracted with ether. The ethereal solution is washed with water until neutral, dried over sodium sulfate and evaporated. The crude product is heated on a steam bath for 90 minutes in 10 ml of pyridine and 10 ml of acetic anhydride. Extraction with ether is then carried out and the ethereal phase washed until neutral with water. The crude crystalline 1α-methyl-?4-androsten-17β-ol-3-one-17- acetateobtained after drying and evaporation of the solution, melts at 122°C to 129°C. Yield 98% of the theoretical.1α-Methyl-?4-androsten-17β-ol-3-one-17-acetate when purified by recrystallization from isopropyl ether melts at 138°C to 139°C.

Therapeutic Function

17β-Hydroxy-1β-methyl-5α-androst-l-ene-3-one acetate

InChI:InChI=1/C20H30O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1

Synthetic route

3-Aethylendioxy-1-methylen-5α-androstanol-(17β) (4360-33-2) → 17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4)

Conditions	Yield
(i) Zn-Cu, I2, CH2I2, Et2O, (ii) aq. H2SO4, MeOH; Multistep reaction;

methenolone enanthate → 17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) + 12β,17β-dihydroxy-1-methyl-5α-androstan-1-ene-3-one + 16β,17β-dihydroxy-1-methyl-5α-androstan-1-ene-3-one + 17β-hydroxy-1-methyl-5α-androstan-1-ene-3,16-dione + 15β,17β-dihydroxy-1-methyl-5α-androstan-1-ene-3-one + 1-methyl-5α-androst-1-ene-3,17-dione (1424-01-7)

Conditions	Yield
With Aspergillus niger In methanol at 26℃; for 288h; Microbiological reaction;

methenolone enanthate → 17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4)

Conditions	Yield
With Cunninghamella blakesleeana In methanol at 26℃; for 288h; Microbiological reaction;

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 17β-(tert.-butyldimethylsilyloxy)-1-methyl-5α-androsta-1-en-3-one (127557-35-1)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature;	96%

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → atamestane (96301-34-7)

Conditions	Yield
With diphenyl diselenide; iodosylbenzene In toluene at 80℃; for 9h;	51%

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) + UDP-glucuronic acid (2616-64-0) → 1-methyl-5α-androst-1-1en-3-one-17β-O-glucuronide + 3α-hydroxy-1-methylen-5α-androstan-17-one glucuronide

Conditions	Yield
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4;	A 24% B 28%

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 1β-Methyl-4,5α-dihydro-testosteron (17β-Hydroxy-1β-methyl-5α-androstan-3-on) (1232-57-1) + mesterolone (1424-00-6)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tributylzinc hydride In tetrahydrofuran for 1h; Heating; Yield given. Yields of byproduct given;

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → (1S,5R,8R,9S,10S,13S,14S,17S)-1,10,13-Trimethyl-17-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one (38631-89-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Tributylzinnhydrid, Azobisisobutyronitril / tetrahydrofuran / 1 h / Heating 2: hexamethyldisilazane / pyridine / 0.25 h View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → (1S,5S,8R,9S,10S,13S,14S,17S)-1,10,13-Trimethyl-17-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one (38631-89-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Tributylzinnhydrid, Azobisisobutyronitril / tetrahydrofuran / 1 h / Heating 2: hexamethyldisilazane / pyridine / 0.25 h View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 1,4-dimethylandrosta-1,4-dien-3,17-dione (127557-29-3)

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C 6: 92 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature 7: 83 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-hydroxy-1,4α-dimethyl-5α-androst-1-en-3-one (127557-37-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 1,4α-dimethyl-5α-androst-1-en-3,17-dione (127557-41-9)

Conditions

Yield

Multi-step reaction with 4 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 84 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-hydroxy-1,2,4α-trimethyl-5α-androst-1-en-3-one (127557-50-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature; 2 View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-hydroxy-1,4-dimethylandrosta-1,4-dien-3-one (127557-40-8)

Conditions

Yield

Multi-step reaction with 6 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C 6: 92 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 1,2,4α-trimethyl-5α-androst-1-en-3,17-dione (127557-51-1)

Conditions

Yield

Multi-step reaction with 8 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature; 2 8: 83 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-hydroxy-1,2,4-trimethylandrosta-1,4-dien-3-one (127557-49-7)

Conditions

Yield

Multi-step reaction with 8 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C 8: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 1,2,4-trimethylandrosta-1,4-dien-3,17-dione (127557-31-7)

Conditions

Yield

Multi-step reaction with 9 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C 8: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature 9: 82 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-acetyloxy-1,4α-dimethyl-5α-androst-1-en-3-one (127557-38-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-acetyloxy-1,2,4α-trimethyl-5α-androst-1-en-3-one (127557-47-5)

Conditions

Yield

Multi-step reaction with 6 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-acetyloxy-1,4-dimethylandrosta-1,4-dien-3-one (127557-39-5)

Conditions

Yield

Multi-step reaction with 5 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-acetyloxy-1,2,4-trimethylandrosta-1,4-dien-3-one (127557-48-6)

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-(tert.-butyldimethylsilyloxy)-1,4α-dimethyl-5α-androsta-1-en-3-one (127557-36-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min View Scheme

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → 17β-acetyloxy-1,4α-dimethyl-2-<(phenylthio)methyl>-5α-androst-1-en-3-one (127557-46-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C View Scheme

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide (24589-78-4) + 17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) → C26H46O2Si2 (136693-28-2)

Conditions	Yield
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h;
With ammonium iodide; ethanethiol In acetonitrile at 80℃; for 0.5h;

Upstream product

• 4360-33-2 3-Aethylendioxy-1-methylen-5α-androstanol-(17β) 

Downstream Products

• 127557-46-4 17β-acetyloxy-1,4α-dimethyl-2-<(phenylthio)methyl>-5α-androst-1-en-3-one 
• 96301-34-7 atamestane 
• 1232-57-1 1β-Methyl-4,5α-dihydro-testosteron (17β-Hydroxy-1β-methyl-5α-androstan-3-on) 
• 1424-00-6 mesterolone 

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Aspergillus Niger-mediated biotransformation of methenolone enanthate, and immunomodulatory activity of its transformed products

Two fungal cultures Aspergillus Niger and Cunninghamella blakesleeana were used for the biotransformation of methenolone enanthate (1). Biotransformation with A. Niger led to the synthesis of three new (2-4), and three known (5-7) metabolites, while fermentation with C. blakesleeana yielded metabolite 6. Substrate 1 and the resulting metabolites were evaluated for their immunomodulatory activities. Substrate 1 was found to be inactive, while metabolites 2 and 3 showed a potent inhibition of ROS generation by whole blood (IC50 = 8.60 and 7.05 μg/mL), as well as from isolated polymorphonuclear leukocytes (PMNs) (IC50 = 14.0 and 4.70 μg/mL), respectively. Moreover, compound 3 (34.21%) moderately inhibited the production of TNF-α, whereas 2 (88.63%) showed a potent inhibition of TNF-α produced by the THP-1 cells. These activities indicated immunomodulatory potential of compounds 2 and 3. All products were found to be non-toxic to 3T3 mouse fibroblast cells.