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| | NORETHYNODREL Basic information |
| Product Name: | NORETHYNODREL | | Synonyms: | NORETHYNDREL;NORETHYNODREL;(17-alpha)-17-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one;(17alpha)-19-norpregn-5(10)-en-20-yn-3-on;13-methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16,17-tetradecahyd;17-alpha-ethinyl-17-beta-hydroxy-delta(sup5(10))-estren-3-one;17alpha-Ethinyl-17beta-hydroxy-delta5(10)-estren-3-one;17-alpha-ethinyl-5,10-estrenolone | | CAS: | 68-23-5 | | MF: | C20H26O2 | | MW: | 298.42 | | EINECS: | 200-682-1 | | Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Miscellaneous Biochemicals;Steroids | | Mol File: | 68-23-5.mol |  |
| | NORETHYNODREL Chemical Properties |
| Melting point | 169-170° | | alpha | D +108° (1% chloroform) | | Boiling point | 379.83°C (rough estimate) | | density | 1.0766 (rough estimate) | | refractive index | 1.4800 (estimate) | | storage temp. | Refrigerator | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | | pka | 13.10±0.40(Predicted) | | form | Solid | | color | White to Off-White | | EPA Substance Registry System | Norethynodrel (68-23-5) |
| | NORETHYNODREL Usage And Synthesis |
| Chemical Properties | White to Off-White Solid | | Originator | Enovid, Searle ,US,1957 | | Uses | Norethynodrel (Norethindrone EP Impurity D) (>90%) is a progestin used in Enovid, an oral contraceptive, also used in the treatment of endometriosis and hypermenorrhea. | | Uses | Norethynodrel is a progestin used in Enovid, an oral contraceptive, also used in the treatment of endometriosis and hypermenorrhea.
| | Definition | ChEBI: Norethynodrel is an oxo steroid. | | Manufacturing Process | Convenient starting materials are the ethers of 3-hydroxy-13-methyl1,4,6,7,8,9,11,12,13,14,16,17-dodecahydro-15H-cyclopenta-α-phenanthren
2474 17-one described in US Patent 2,655,518, according to US Patent 2,691,028 where the following preparation is also described. The methyl ether is also designated as 3-methoxy-17-oxo-2,5-estradiene
A stirred solution of 10.6 parts of 3-methoxy-13-methyl-1,4,6,7,8,9,11,12,13, 14,16,17dodecahydro-15H-cyclopenta-α-phenanthren-17-one in 700 parts of anhydrous ether and 45 parts of dry toluene is cooled to 0°C and saturated with dry acetylene. While a slow stream of acetylene is passed through the reaction mixture, a solution of 20 parts of potassium t-amylate in 135 parts of anhydrous t-pentanol is added in the course of 15 minutes with stirring. Passage of acetylene and stirring are continued for an additional 4? hours. After standing at 0°C for 16 hours, the mixture is washed with aqueous ammonium chloride solution until the aqueous phase is neutral, then with water and saturated sodium chloride solution. The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to a residue of about 250 parts. 500 parts of petroleum ether are added and after standing at 0°C for an hour, the mixture is filtered. The collected precipitate is recrystallized from ether. The resulting 3-methoxy-13-methyl-17-ethynyl1,4,6,7,8,9,11,12,13,14,16,17-dodecahydro-15H-cyclopenta-α-phenanthren17-ol melts at about 181° to 182°C.
To a refluxing solution of 10 parts of 3-methoxy-17-ethynyl-17-hydroxy-13methyl-1,4,6,7,8,9,11,12,13,14,16,17-dodecahydro-15H-cyclopenta-αphenanthrene in 500 parts of methanol, 20 parts of glacial acetic acid are added. Refluxing is continued for 7 minutes, water is added to the point of turbidity and the reaction mixture is permitted to come to room temperature. The precipitate is collected on a filter and recrystallized from aqueous methanol. The 13-methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14, 16,17-tetradecahydro-15H-cyclopenta-α-phenanthren-3-one thus obtained melts at about 169° to 170°C.
| | Therapeutic Function | Progestin | | Safety Profile | Suspected carcinogen
with experimental tumorigenic data. Human
and experimental reproductive effects.
Mutation data reported. When heated to
decomposition it emits acrid smoke and
irritating fumes. |
| | NORETHYNODREL Preparation Products And Raw materials |
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