ChemicalBook > CAS DataBase List > NORETHYNODREL

NORETHYNODREL

Product Name
NORETHYNODREL
CAS No.
68-23-5
Chemical Name
NORETHYNODREL
Synonyms
Enavid;Enovid;Enidrel;SC-4642;Lynestrol;NSC-15432;Infecundin;NORETHYNDREL;Noretynodrel;NORETHYNODREL
CBNumber
CB9339123
Molecular Formula
C20H26O2
Formula Weight
298.42
MOL File
68-23-5.mol
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NORETHYNODREL Property

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)
form 
Solid
pka
13.10±0.40(Predicted)
color 
White to Off-White
EPA Substance Registry System
Norethynodrel (68-23-5)
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Safety

Hazard Codes 
T
Risk Statements 
45-61
Safety Statements 
53-22-36/37/39-45
WGK Germany 
3
RTECS 
RC8980000
Hazardous Substances Data
68-23-5(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H350May cause cancer

H360May damage fertility or the unborn child

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
R188441
Product name
17-ALPHA-ETHYNYL-17-BETA-HYDROXYESTR-5(10)-EN-3-ONE
Purity
AldrichCPR
Packaging
1MG
Price
$29.8
Updated
2024/03/01
TRC
Product number
N676020
Product name
Norethynodrel
Packaging
1mg
Price
$100
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
SHG0020345
Product name
NORETHYNODREL
Purity
95.00%
Packaging
1MG
Price
$252
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
71745
Product name
Norethynodrel
Packaging
2.5mg
Price
$650
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
SHG0020345
Product name
NORETHYNODREL
Purity
95.00%
Packaging
2.5MG
Price
$715
Updated
2021/12/16
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NORETHYNODREL Chemical Properties,Usage,Production

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

Raw materials

Preparation Products

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View Lastest Price from NORETHYNODREL manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
NORETHYNODREL 68-23-5
Price
US $1.10/g
Min. Order
1g
Purity
99.0% min
Supply Ability
100 tons min
Release date
2021-05-26
Meihua Biological Technology Co.,Ltd
Product
Norethynodrel 68-23-5
Price
US $10.00/KG
Min. Order
10G
Purity
99%
Supply Ability
1000kg
Release date
2018-05-08

68-23-5, NORETHYNODRELRelated Search:

3-CYCLOHEXYL-1-PROPYNE CYCLOPENTYLACETYLENE 3,4-DIMETHYL-1-PENTYN-3-OL 3,5-DIMETHYL-1-HEXYN-3-OL 3-ETHYL-1-HEPTYN-3-OL Tibolone 1-ETHYNYLCYCLOPENTANOL 1-HEXADECYNE 3-METHYL-1-DODECYN-3-OL 4-ETHYL-1-OCTYN-3-OL 3,6-DIMETHYL-1-HEPTYN-3-OL 3,4,4-TRIMETHYL-1-PENTYN-3-OL NORETHYNODREL 3-METHYL-1-NONYN-3-OL 1-OCTADECYNE 1-PENTADECYNE Norethindrone NOR-1

  • 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-delta<sup>5(10)</sup>-estren-3-one
  • 17-alpha-ethinyl-5,10-estrenolone
  • 17alpha-Ethinyl-5,10-estrenolone
  • 17alpha-Ethinyl-delta(sup)-5,10-19-nortestosterone
  • 17-alpha-Ethinyl-delta(super)-5,10-19-nortestosterone
  • 17-alpha-ethinyl-estra(5,10)eneolone
  • 17alpha-Ethinyl-estra(5,10)eneolone
  • 17-alpha-ethinyls-5,10-estrenolone
  • Norethindrone Impurity 4（Norethindrone EP Impurity D）
  • 17-alpha-ethynyl-17-beta-hydroxy-3-oxo-delta(sup5(10))-estrene
  • 17alpha-Ethynyl-17beta-hydroxy-3-oxo-delta<sup>5(10)</sup>-estrene
  • 17-alpha-Ethynyl-17-beta-hydroxy-delta(sup. 5(10))-estren-3-one
  • 17-alpha-ethynyl-17-beta-hydroxy-delta(sup.5(10))-estren-3-one
  • 17alpha-Ethynyl-17beta-hydroxy-delta<sup>5(10)</sup>-estren-3-one
  • 17-alpha-ethynyl-17-beta-hydroxyester-5(10)-en-3-one
  • 17-alpha-ethynyl-17-beta-hydroxyestr-5(10)-en-3-one
  • 17alpha-Ethynyl-17beta-hydroxyestr-5(10)-en-3-one
  • 17-alpha-ethynyl-17-hydroxy-5(10)-estren-3-one
  • 17alpha-Ethynyl-17-hydroxy-5(10)-estren-3-one
  • 17-alpha-Ethynyl-17-hydroxyestr-5(10)-en-3-one
  • 17-alpha-ethynyl-19-nor-5(10)-androsten-17-beta-ol-3-one
  • 17alpha-Ethynyl-19-nor-5(10)-androsten-17beta-ol-3-one
  • 17-alpha-ethynyl-19-nor-s(10)-androsten-17-beta-ol-3-one
  • 17-alpha-ethynyl-5(10)-estren-17-ol-3-one
  • 17alpha-Ethynyl-5(10)-estren-17-ol-3-one
  • 17-alpha-ethynylestr-5(10)-en-17-beta-ol-3-one
  • 17alpha-Ethynylestr-5(10)-en-17beta-ol-3-one
  • 17-alpha-ethynyl-estr-5(10)-en-3-on-17-beta-ol
  • 17alpha-Ethynyl-estr-5(10)-en-3-on-17beta-ol
  • 17alpha-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one
  • 17-beta-Hydroxy-17-alpha-ethinyl-5(10)-estren-3-one
  • 17-Ethinyl-5(10)-estraeneolone
  • 17-Ethynyl-17-hydroxyestr-5(10)-en-3-one
  • 17-hydroxy(17-alpha)-19-norpregn-5(10)-en-20-yn-3-one
  • 17-Hydroxy(17alpha)-19-norpregn-5(10)-en-20-yn-3-one
  • 17-hydroxy-19-nor-17-alpha-pregn-5(10)-en-20-yn-3-on
  • 17-hydroxy-19-nor-17alpha-pregn-5(10)-en-20-yn-3-on
  • 17-hydroxy-19-nor-17-alpha-pregn-5(10)-en-20-yn-3-one
  • 17-Hydroxy-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one
  • 19-nor-17alpha-Pregn-5(10)-en-20-yn-3-one, 17-hydroxy-
  • 19-Nor-ethinyl-5,10-testosterone
  • 19-Norethynodrel
  • 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-, (17alpha)-
  • component of Conovid e
  • component of Enovid
  • Enavid
  • Enidrel
  • Enovid
  • Estr-5(10)-en-3-one, 17alpha-ethynyl-17-hydroxy-
  • Infecundin
  • Lynestrol
  • Norethinodrel