Product Name

  • Name

    Norethindrone

  • EINECS 200-681-6
  • CAS No. 68-22-4
  • Article Data47
  • CAS DataBase
  • Density 1.15 g/cm3
  • Solubility chloroform: ≥50 mg/mL, clear, colorless
  • Melting Point 205-206 °C(lit.)
  • Formula C20H26O2
  • Boiling Point 447 °C at 760 mmHg
  • Molecular Weight 298.425
  • Flash Point 190.5 °C
  • Transport Information
  • Appearance Off-white to pale yellow solid
  • Safety 22-36/37/39-45-26
  • Risk Codes 40-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 68-22-4 (Norethindrone)
  • Hazard Symbols HarmfulXn
  • Synonyms Norethindrone;
  • PSA 37.30000
  • LogP 3.49250

Synthetic route

estra-4-ene-3,17-dione
734-32-7

estra-4-ene-3,17-dione

acetylene
74-86-2

acetylene

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Stage #1: estra-4-ene-3,17-dione With potassium hydroxide In toluene; tert-butyl alcohol under 760.051 Torr; for 0.166667h; Reflux; Industrial scale;
Stage #2: acetylene In tert-butyl methyl ether; toluene for 6h; Industrial scale;		100%
With potassium tert-butylate; acetone
3-ethoxy-19-nor-3,5-androstadiene-17-one
2863-88-9

3-ethoxy-19-nor-3,5-androstadiene-17-one

acetylene
74-86-2

acetylene

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With potassium In tert-Amyl alcohol; toluene at 20℃; Inert atmosphere;88%
With potassium 2-methylbutan-2-olate
Noretynodrel
5541-86-6, 6073-48-9, 13577-86-1, 25918-97-2, 57287-11-3, 68-23-5

Noretynodrel

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With potassium hydroxide In methanol; water Ambient temperature;86%
hydroxide In water at 30℃; Rate constant; Kinetics; Mechanism; other catalysts used;
19-nor-17α-pregn-4-en-20-yne-3β,17-diol diacetate
297-76-7

19-nor-17α-pregn-4-en-20-yne-3β,17-diol diacetate

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With Trichothecium roseum for 288h; Microbiological reaction;6.67%
estrone 3-methyl ether
1624-62-0

estrone 3-methyl ether

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
ueber mehrere Stufen;
3-methoxy-19-nor-17βH-pregna-2,5(10)-dien-20-yn-17-ol
19357-36-9

3-methoxy-19-nor-17βH-pregna-2,5(10)-dien-20-yn-17-ol

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With hydrogenchloride
3-methoxyestra-2,5(10)-dien-17-one
17976-32-8

3-methoxyestra-2,5(10)-dien-17-one

acetylene
74-86-2

acetylene

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With hydrogenchloride; potassium tert-butylate 1.) THF, 1 h, -10 deg C; 2.) MeOH, 60-70 deg C, 2 h; Yield given. Multistep reaction;
estra-4-ene-3,17-dione
734-32-7

estra-4-ene-3,17-dione

potassium acetylenide

potassium acetylenide

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With ammonia
3-methoxy-17-hydroxyestra-2,5(10)-diene
1091-93-6

3-methoxy-17-hydroxyestra-2,5(10)-diene

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 63 percent / aluminium isopropylate, 2-butanone / benzene / 15 h
2: 1.) K(t-BuO); 2.) conc. HCl / 1.) THF, 1 h, -10 deg C; 2.) MeOH, 60-70 deg C, 2 h
View Scheme
Multi-step reaction with 3 steps
1: aluminum isopropoxide; sodium sulfate / methanol; water; cyclohexanone; toluene
2: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE
3: hydrogenchloride / methanol; water
View Scheme
3-Methoxy-6,7:8,9-diseco-1,3,5(10),7-oestratetraen-11,17-dion
75863-04-6

3-Methoxy-6,7:8,9-diseco-1,3,5(10),7-oestratetraen-11,17-dion

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: 63 percent / aluminium isopropylate, 2-butanone / benzene / 15 h
3: 1.) K(t-BuO); 2.) conc. HCl / 1.) THF, 1 h, -10 deg C; 2.) MeOH, 60-70 deg C, 2 h
View Scheme
19-nortestosterone
434-22-0

19-nortestosterone

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CrO3
3: potassium tert-pentylate
View Scheme
estra-4-ene-3,17-dione
734-32-7

estra-4-ene-3,17-dione

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: potassium tert-pentylate
View Scheme
Multi-step reaction with 3 steps
1: pyridine hydrochloride / 30 °C
2: potassium tert-butylate / acetone / 0 °C
3: hydrogenchloride / tetrahydrofuran; water / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 60 °C
2: potassium ethoxide / toluene / 50 °C
3: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: Pyridine hydrobromide / 20 °C
2: potassium 2-methylpropan-2-olate / tetrahydrofuran / 20 °C
3: hydrogenchloride / acetone; water / 10 °C
View Scheme
diethyl ether ethyl acetate

diethyl ether ethyl acetate

3-methoxy-19-nor-17βH-pregna-2,5(10)-dien-20-yn-17-ol
19357-36-9

3-methoxy-19-nor-17βH-pregna-2,5(10)-dien-20-yn-17-ol

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With hydrogenchloride In methanol; water
With hydrogenchloride In methanol; water
19-hydroxy-4-androstene-3,17-dione
510-64-5

19-hydroxy-4-androstene-3,17-dione

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; ethyl acetate / 4.5 h / 55 - 65 °C
2: sodium chlorite; sodium dihydrogenphosphate / tert-butyl alcohol; water / 2.5 h / 20 °C
3: hydrogenchloride / water; acetone
4: pyridine hydrochloride / toluene; ethanol / Reflux
5: potassium / toluene; tert-Amyl alcohol / 20 °C / Inert atmosphere
View Scheme
19-oxoandrostenedione
968-49-0

19-oxoandrostenedione

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium chlorite; sodium dihydrogenphosphate / tert-butyl alcohol; water / 2.5 h / 20 °C
2: hydrogenchloride / water; acetone
3: pyridine hydrochloride / toluene; ethanol / Reflux
4: potassium / toluene; tert-Amyl alcohol / 20 °C / Inert atmosphere
View Scheme
androst-4-ene-3,17-dion-19-oic acid
4757-95-3

androst-4-ene-3,17-dion-19-oic acid

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; acetone
2: pyridine hydrochloride / toluene; ethanol / Reflux
3: potassium / toluene; tert-Amyl alcohol / 20 °C / Inert atmosphere
View Scheme
octanol
111-87-5

octanol

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ammonium chloride; lithium / tetrahydrofuran; ethanol; ammonia; water
2: aluminum isopropoxide; sodium sulfate / methanol; water; cyclohexanone; toluene
3: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE
4: hydrogenchloride / methanol; water
View Scheme
3-methoxyestra-2,5(10)-dien-17-one
17976-32-8

3-methoxyestra-2,5(10)-dien-17-one

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE
2: hydrogenchloride / methanol; water
View Scheme
3-ethoxy-17α-ethynyl-19-desmethylpregna-3,5-diene-17β-ol
96487-85-3

3-ethoxy-17α-ethynyl-19-desmethylpregna-3,5-diene-17β-ol

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 10℃;45.1 g
C24H33NO

C24H33NO

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With sulfuric acid In 2-methyltetrahydrofuran; water at 0℃;45.5 g
3-methoxy-19-norandrosta-3,5-dien-17-one
17976-34-0

3-methoxy-19-norandrosta-3,5-dien-17-one

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium tert-butylate / acetone / 0 °C
2: hydrogenchloride / tetrahydrofuran; water / 50 °C
View Scheme
3-ethoxy-19-nor-3,5-androstadiene-17-one
2863-88-9

3-ethoxy-19-nor-3,5-androstadiene-17-one

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium 2-methylpropan-2-olate / tetrahydrofuran / 20 °C
2: hydrogenchloride / acetone; water / 10 °C
View Scheme
(8R,9S,10R,13S,14S)-13-Methyl-3-pyrrolidin-1-yl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthren-17-one

(8R,9S,10R,13S,14S)-13-Methyl-3-pyrrolidin-1-yl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthren-17-one

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium ethoxide / toluene / 50 °C
2: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C
View Scheme
C21H28O2

C21H28O2

norethisterone
68-22-4

norethisterone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 50℃;45.3 g
norethisterone
68-22-4

norethisterone

acetic acid
64-19-7

acetic acid

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
With sodium carbonate; trifluoroacetic anhydride In benzene for 0.5h; Ambient temperature;96.5%
Stage #1: acetic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 0.5h; Inert atmosphere;
Stage #2: norethisterone With dmap In chloroform for 18h; Inert atmosphere; Reflux;		93%
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃;91.6%
In trifluoroacetic acid90%
With benzenesulfonyl chloride In pyridine for 48h;79%
norethisterone
68-22-4

norethisterone

17,17a-dimethyl-D-homogona-4,13,15,17(17a)-tetraen-3-one
99998-43-3

17,17a-dimethyl-D-homogona-4,13,15,17(17a)-tetraen-3-one

Conditions
ConditionsYield
With formic acid at 95 - 100℃; for 2h;96%
With formic acid
With formic acid; toluene-4-sulfonic acid
Multi-step reaction with 2 steps
1: 95 percent / dimethylformamide / 0.5 h / 0 - 5 °C
2: 47 percent / formic acid / 0.67 h
View Scheme
norethisterone
68-22-4

norethisterone

(S)-acetylproline
68-95-1

(S)-acetylproline

17-(N-acetylpyrrolidino-2'-carbonyl)oxy-19-norpregn-4-en-20-yn-3-one

17-(N-acetylpyrrolidino-2'-carbonyl)oxy-19-norpregn-4-en-20-yn-3-one

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 16h; Ambient temperature;95.5%
norethisterone
68-22-4

norethisterone

N-Cbz-Ala
1142-20-7

N-Cbz-Ala

(S)-2-Benzyloxycarbonylamino-propionic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

(S)-2-Benzyloxycarbonylamino-propionic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;95%

Norethindrone Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 294.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Norethindrone Specification

Norethindrone is one kind of off-white to pale yellow solid. The IUPAC Name of this chemical is (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one. Its' system names are (1)19-Nor-17-alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-; (2)19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy- (8CI); (3)19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-; (4)Norethisterone. And it belongs to the following product categories: (1)Active Pharmaceutical Ingredients; (2)Acetylenes; (3)Biochemistry; (4)Functionalized Acetylenes; (5)Hydroxyketosteroids; (6)Steroids; (7)Intermediates & Fine Chemicals; (8)Pharmaceuticals. Norethindrone can be manufactured from acetate pregnancy pregnenolone synthesis.

Physical properties about Norethindrone are: (1)ACD/LogP: 2.858; (2)ACD/LogD (pH 5.5): 2.86; (3)ACD/LogD (pH 7.4): 2.86; (4)ACD/BCF (pH 5.5): 87.57; (5)ACD/BCF (pH 7.4): 87.57; (6)ACD/KOC (pH 5.5): 854.94; (7)ACD/KOC (pH 7.4): 854.94; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.577; (12)Molar Refractivity: 85.551 cm3; (13)Molar Volume: 258.097 cm3; (14)Polarizability: 33.915 10-24cm3; (15)Surface Tension: 49.0810012817383 dyne/cm; (16)Density: 1.156 g/cm3; (17)Flash Point: 190.465 °C; (18)Enthalpy of Vaporization: 81.378 kJ/mol; (19)Boiling Point: 446.98 °C at 760 mmHg

Uses of Norethindrone: It is used in some combined oral contraceptive pills and in some progestogen only pills. It is a progestogen and can be used to treat premenstrual syndrome, painful periods, abnormal heavy bleeding, irregular periods, menopausal syndrome (in combination with oestrogen), or to postpone a period.

When you are using this chemical, please be cautious about it as the following:
1. Do not breathe dust;
2. Wear suitable protective clothing, gloves and eye/face protection;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. Wear suitable gloves and eye/face protection;
5. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1;
(2)InChIKey=VIKNJXKGJWUCNN-XGXHKTLJSA-N;
(3)Smiles[C@@H]12[C@@]([C@@](CC2)(C#C)O)(CC[C@H]2[C@H]1CCC1=CC(=O)CC[C@H]21)C;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 6gm/kg (6000mg/kg)   Drugs in Japan Vol. -, Pg. 809, 1990.
women TDLo oral 42mg/kg (42mg/kg) ENDOCRINE: ANDROGENIC

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 American Journal of Obstetrics and Gynecology. Vol. 84, Pg. 962, 1962.

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