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Norethindrone

Product Name
Norethindrone
CAS No.
68-22-4
Chemical Name
Norethindrone
Synonyms
Elk;ENT;NET;Cek6;Elkh;Hek6;EPB1;EPHB1;EPHT2;EPTH2
CBNumber
CB0455127
Molecular Formula
C20H26O2
Formula Weight
298.42
MOL File
68-22-4.mol
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Norethindrone Property

Melting point:
205-206 °C(lit.)
Boiling point:
379.83°C (rough estimate)
alpha 
D20 -31.7° (chloroform); D20 -25° (chloroform)
Density 
1.0766 (rough estimate)
refractive index 
1.4800 (estimate)
storage temp. 
-20°C Freezer
solubility 
chloroform: ≥50 mg/mL, clear, colorless
form 
powder
pka
13.09±0.40(Predicted)
color 
white to off-white
Water Solubility 
7.043mg/L(25 ºC)
Merck 
6697
BRN 
1915671
InChIKey
VIKNJXKGJWUCNN-XGXHKTLJSA-N
CAS DataBase Reference
68-22-4(CAS DataBase Reference)
NIST Chemistry Reference
Norethindrone(68-22-4)
EPA Substance Registry System
Norethisterone (68-22-4)
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Safety

Hazard Codes 
Xn
Risk Statements 
40-36/37/38-20/21/22
Safety Statements 
22-36/37/39-45-37/39-26
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
RTECS 
RC8975000
HS Code 
29144000
Hazardous Substances Data
68-22-4(Hazardous Substances Data)
Toxicity
LD50 oral in mouse: 6gm/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H351Suspected of causing cancer

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
N4128
Product name
19-Norethindrone
Purity
≥98%, powder
Packaging
1g
Price
$186
Updated
2020/08/18
Sigma-Aldrich
Product number
1469005
Product name
Norethindrone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$366
Updated
2020/08/18
Cayman Chemical
Product number
20941
Product name
Norethindrone
Purity
≥98%
Packaging
250mg
Price
$25
Updated
2020/06/24
Cayman Chemical
Product number
20941
Product name
Norethindrone
Purity
≥98%
Packaging
500mg
Price
$45
Updated
2020/06/24
Sigma-Aldrich
Product number
N4128
Product name
19-Norethindrone
Purity
≥98%, powder
Packaging
250mg
Price
$79.7
Updated
2020/08/18
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Norethindrone Chemical Properties,Usage,Production

Description

Norethindrone is a progestin (a synthetic substance with properties similar to progesterone) that is best known as the first female oral contraceptive, or the “pill.”Norethindrone’s global impact on society and culture has made it one of the most important inventions in history.

Chemical Properties

Off-White to Pale Yellow Solid

Originator

Norlutin,Parke Davis ,US,1957

History

The development of norethindrone as a female oral contraceptive took place indirectly over 30 years as a result of steroid research.This research accelerated in the 1930s when structures and medical applications of steroidal compounds were determined.Steroids are lipids, which include cholesterol, bile salts,and sex hormones,that are characterized by a structure of three fused six-carbon rings and a five-carbon ring.
In 1957, both norethindrone and norethynodrel were approved by the Food and Drug Administration (FDA) for treating menstrual problems and infertility. In 1960, the FDA approved Searle's norethynodrel under the trade name Enovid. Norethindrone was approved as an oral contraceptive in 1962 under the trade name Ortho-Novum.

Uses

Progestin contraceptives work by producing pregnant-like conditions in a female to preventovulation.During pregnancy, progesterone is released by the placenta during development ofthe fetus.This in turn suppresses development of egg follicles and ovulation. Progestins mimicthis condition and thus prevent or delay ovulation.Oral contraceptives currently use progestinand estrogen in combination to prevent ovulation and thicken cervical mucus.The latter makeit harder for sperm to enter the uterus and for an egg to implant on the uterine wall.

Uses

progestogen

Uses

A synthetic progestin

Uses

Progesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen

Definition

ChEBI: A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.

Manufacturing Process

7.5 grams of 3-methoxyestrone were dissolved in 750 cc of anhydrous dioxane in a three-neck flask, placed in a box and insulated with cotton wool. 2 liters of anhydrous liquid ammonia and 15 grams of lithium metal in the form of wire were added to the mechanically stirred solution. After stirring for one hour, 150 cc of absolute ethanol were added at such speed that no bumping occurred; when the blue color had disappeared, 500 cc of water were added in the same way. The ammonia was evaporated on the steam bath and the product collected with 2 liters of water. It was extracted with ether and then with ethyl acetate and the combined extract was washed to neutral and evaporated to dryness under vacuum, leaving 7.4 grams of a slightly yellow oil.
The oil thus obtained was dissolved in 400 cc of methanol and refluxed during one hour with 150 cc of 4N hydrochloric acid. The mixture was poured into a sodium chloride solution and extracted with ethyl acetate, washed to neutral, dried and evaporated to dryness. The product was a yellow oil which showed an ultraviolet absorption maximum characteristic of a ?4-3-ketone.
A solution of 2.7 grams of chromic acid in 20 cc of water and 50 cc of acetic acid was added to the stirred solution of the above oil in 100 cc of acetic acid, maintaining the temperature below 20°C. After 90 minutes standing, 50 cc of methanol were added and the mixture concentrated under vacuum (20 mm). The residue was extracted with ether, washed to neutral and evaporated to dryness. The residual semicrystalline product (7 grams) was chromatographed over alumina and the fractions eluted with ether yielded 3.2 grams of ?4-19norandrosten-3,17-dione having a MP of 163° to 167°C.
A solution of 2 grams of ?4-19-norandrosten-3,17-dione and 0.4 gram of pyridine hydrochloride in 50 cc of benzene free of thiophene was made free of moisture by distilling a small portion; 4 cc of absolute alcohol and 4 cc of ethyl orthoformate were added and the mixture was refluxed during 3 hours. 5 cc of the mixture were then distilled and after adding an additional 4 cc of ethyl orthoformate the refluxing was continued for 2 hours longer. The mixture was evaporated to dryness under vacuum and the residue was taken up in ether, washed, dried and evaporated to dryness. The residue was crystallized from hexane-acetone and then from ether to give ?3,5-19-nor-3ethoxy-androstadien-17-onewith a MP of 140° to 142°C.
One gram of potassium metal was dissolved in 25 cc of tertiary amyl alcohol by heating under an atmosphere of nitrogen. One gram of ?3,5-19-nor-3ethoxyandrostadien-17-onein 25 cc of anhydrous toluene was added and nitrogen was passed during 15 minutes. Then acetylene (especially dried and purified) was passed during 14 hours through the mechanically stirred solution, at room temperature.
The mixture was poured in water, acidified to pH 1 with dilute hydrochloric acid, heated on the steam bath for 30 minutes and then subjected to steam distillation to remove the organic solvents. The residue was filtered, dried and recystallized several times from ethyl acetate. The ?4-19-nor-17αethinylandrosten-17β-ol-3-onethus obtained had a MP of 198° to 200°C (in sulfuric acid bath), 200° to 204°C (Kofler).

brand name

Camila (Barr); Errin (Barr); Micronor (OrthoMcNeil); Nor-QD (Watson); Norlutin (Parke-Davis).

Therapeutic Function

Progestin

General Description

Norethindrone, 17α-ethinyl-19-nortestosterone, and itsΔ5(10)-isomer, norethynodrel, might appear at first glance tobe subtle copies of each other. One would predict that theΔ5(10)-double bond would isomerize in the stomach’s acid tothe Δ4-position. However, the two drugs were actually developedsimultaneously and independently; hence, neither can beconsidered a copy of the other. Furthermore, norethindrone isabout 10 times more active than norethynodrel, indicating that isomerization is not as facile in vivo asone might predict. Although they are less active than progesteronewhen given subcutaneously, they have the importantadvantage of being orally active. The discovery of the potentprogestin activity of 17α-ethinyltestosterone (ethisterone) and19-norprogesterone preceded the development of these potentprogestins. Both are orally active, with the 17α-ethinyl groupblocking oxidation to the less active 17-one. The rich electrondensity of the ethinyl group and the absence of the 19-methylgroup greatly enhance progestin activity. Both compoundswere of great importance as progestin components of oralcontraceptives, although currently, use of norethynodrel isminimal. Norethindrone, USP, and norethindrone acetate,USP, are widely used for all the usual indications of the progestins,as well as being components of oral contraceptives.Because these compounds retain key features of the testosteronestructure, including the 17β-OH, it is not surprisingthat they possess some androgenic side effects.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Mddly toxic by ingestion. Human systemic effects by ingestion: dermatitis and androgenic effects. Human teratogenic effects: developmental abnormalities of the musculoskeletal system and urogenital system; and behavioral effects in the newborn. Human reproductive effects: spermatogenesis; testes, epididymis, sperm duct changes; impotence; male breast development; other male effects; ovaries, fallopian tube changes; menstrual cycle effects; postpartum effects; changes in female fertility. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Carcinogenicity

Norethisterone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Norethindrone Preparation Products And Raw materials

Raw materials

Preparation Products

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Norethindrone Suppliers

J & K SCIENTIFIC LTD.
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010-82848833- ;010-82848833-
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86-10-82849933
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jkinfo@jkchemical.com;market6@jkchemical.com
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China
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96815
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3B Pharmachem (Wuhan) International Co.,Ltd.
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Adamas Reagent, Ltd.
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400-600-9262
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LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
1938
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Nanjing Chemlin Chemical Co., Ltd
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025-83697070-
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+86-25-83453306
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19994
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Chemsky(shanghai)International Co.,Ltd.
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XiaoGan ShenYuan ChemPharm co,ltd
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Syntechem Co.,Ltd
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Tianjin heowns Biochemical Technology Co., Ltd.
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400 638 7771
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sales@heowns.com
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China
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Sinopharm Chemical Reagent Co,Ltd.
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86-21-63210123
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86-21-63290778 86-21-63218885
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View Lastest Price from Norethindrone manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Norethindrone 68-22-4
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-08
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Norethindrone 68-22-4
Price
US $0.00/KG
Min. Order
1g
Purity
99%
Supply Ability
100kg
Release date
2020-10-14
Hebei Lihe Biotechnology Co.,Ltd
Product
17a-ethynyl-19-nortestosterone 68-22-4
Price
US $36.00/KG/Tin
Min. Order
10g
Purity
99%
Supply Ability
10tons
Release date
2020-10-19

68-22-4, NorethindroneRelated Search:


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