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Steroids and sterols

Norethynodrel

Also known as Noretynodrel, Enidrel, Norethinodrel

CAS 68-23-5Formula C20H26O2Molar mass 298.43 g/molEC 200-682-1
GHS signal word: Danger. Pictograms: Serious health hazard 15 suppliers listed
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Norethynodrel chemical structure, C20H26O2, CAS 68-23-5
2D chemical structure

Key facts

What buyers check first

All properties
Appearance
Crystals from aqueous methanol
Melting point
170 °C
Solubility
Very slightly soluble in water, freely soluble in chloroform, soluble in acetone, sparin…
HS code
293723
Category
Steroids and sterols
Illustrative photo, a shrink wrapped pallet of kraft paper sacks in a chemical plant
Typical packagingIllustrative packaging image, not the actual product

What is Norethynodrel?

Plain description, key identifiers and synonyms

Norethynodrel is an oxo steroid.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS number
68-23-5 CAS number cross-checked
EC number
200-682-1
Molecular formula
C20H26O2
UNII
88181ACA0M
InChIKey
ICTXHFFSOAJUMG-SLHNCBLASA-N
InChI
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/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1
Canonical SMILES
C#CC1(O)CCC2C3CCC4=C(CCC(=O)C4)C3CCC21C
Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3CCC(=O)C4

Synonyms

  • Noretynodrel
  • Enidrel
  • Norethinodrel
  • Lynestrol
  • 19-Norethynodrel
  • Noretinodrel
  • Noretynodrelum
  • 19-Nor-ethinyl-5,10-testosterone
  • 17-alpha-Ethynyl-5(10)-estren-17-ol-3-one
  • (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
  • 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-, (17alpha)-
  • 17-alpha-Ethynyl-estr-5(10)-en-3-on-17-beta-ol
  • 17-beta-Hydroxy-17-alpha-ethinyl-5(10)-estren-3-one
  • (17-alpha)-17-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one
  • 19-Nor-17alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-
  • 17-alpha-Ethinyl-17-beta-hydroxy-delta(sup 5(10))-estren-3-one
  • 17-alpha-Ethynyl-17-beta-hydroxy-3-oxo-delta(sup 5(10))-estrene
  • 17-alpha-Ethynyl-17-beta-hydroxy-delta(sup. 5(10))-estren-3-one
  • (17beta-ethynyl-17-hydroxyestr-5(10)-en-3-one
  • (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-3-one
  • 17-Ethinyl-5(10)-estraeneolone
  • Norethinynodrel
  • Norethynodral
  • 17-Hydroxy-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one
  • Noretynodrel (INN)
Show all 33 synonyms
  • Norethynodrel (USAN)
  • Norethynodrel (>90%)
  • (1R,3aS,3bR,9bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,6H,7H,8H,9H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
  • Norethindrone EP Impurity D
  • (17beta)-17-ethynyl-17-hydroxyestr-5(10)-en-3-one
  • 17alpha-Ethinyl-5,10-estrenolone
  • 17-alpha-Ethinyl-5,10-estrenolone
  • Norethynodrel [Progestins]

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Appearance
Crystals from aqueous methanolexp.
Odour
Odorlessexp.
Melting point
170 °Cexp.
Solubility
Very slightly soluble in water, freely soluble in chloroform, soluble in acetone, sparingly soluble in ethanol.exp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
298.43 g/molcalc.
Exact mass
298.1933 Dacalc.
LogP (octanol/water)
3.64calc.
Topological polar surface area
37.3 Ųcalc.
Hydrogen bond donors
1calc.
Hydrogen bond acceptors
2calc.
Rotatable bonds
0calc.
Heavy atoms
22calc.
Rings
4calc.
Aromatic rings
0calc.
Fraction sp3 carbons
0.75calc.
Formal charge
0calc.
Stereocentres
5calc.
Lipinski rule of five
Passes (0 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, O=C1CCC2=C(CCC3C2CCC2CCCC23)C1

O=C1CCC2=C(CCC3C2CCC2CCCC23)C1

4 rings, 18 atoms.

22 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Danger
GHS08: Serious health hazard
Serious health hazard

Hazard statements

  • H350May cause cancer.
  • H360May damage fertility or the unborn child.
Precautionary statements (5)
  • P203Obtain, read and follow all safety instructions before use.
  • P280Wear protective gloves, protective clothing, eye protection and face protection.
  • P318If exposed or concerned, get medical advice.
  • P405Store locked up.
  • P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Norethynodrel suppliers

Sponsored listings first, then the documented ranking: membership, verification, replies, completeness, freshness and ratings

All 15 suppliers
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Where suppliers are based

15 suppliers in 6 countries

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Norethynodrel price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Therapeutic category: Progestogen. In combination with estrogen as contraceptive (oral) (Former).

Use classes: Pharmaceuticals.

Pharmacological actions

  • Contraceptives, Oral, Hormonal
  • Contraceptives, Oral, Synthetic

How it is made

Probably by conversion of oestrone to its methyl ether, reduction to the 1,4-dihydroaromatic compd, oppenauer oxidation to the 17-ketone, reaction with acetylene to produce the 17-ethynyl carbinol, and then hydrolysis with a weak acid

Synthesis of norethynodrel...addition of hypochloric acid to androstenolone acetate gives the corresponding chlorohydrin. On reaction with lead tetraacetate and iodine, the chlorohydrin is converted to a cyclic ether, which in turn is saponified and oxidized to give a diketone.

Read more

Reductive opening of the cyclic ether ring with zinc in glacial acetic acid produces a 19-hydroxy derivative, and subsequent oxidation with chromic acid gives the 10beta-carboxylic acid, which is decarboxylated to the diketone by heating with pyridine. Partial ketalization yields the acetal, and ethynylation with sodium acetylide followed by treatment with either a weak acid (malonic acid)... finally yields norethynodrel...

Prepared by simultaneously saponifying and oxidizing dehydroepiandrosterone acetate by a series of reactions to 19-hydroxyandrost-6(6)-ene-3,17-dione. The hydroxymethyl group at the 10-position is then oxidized to carboxyl. The resulting acid is decarboxylated with simultaneous shifting of the double bond to give oestr-5(10)-ene-3,17-dione. Selective addition of acetylene at the expense of the 17-keto group yields norethynodrel.

Regulatory status

Inventories, regulations and trade controls that list this substance

No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Norethynodrel is traded under.

HS 2937.23Indicative HS code

Oestrogens and progestogens

World exports in 2024
$762M
−2.3% vs 2023, imports $693M
2019 to 2024
Top exporters
  1. China42.9%
  2. Italy18.4%
  3. Netherlands8.9%
Top importers
  1. India * partner reported12.1%
  2. United States11.0%
  3. Belgium8.3%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Norethynodrel is indicative (it is known at chapter level only). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Norethynodrel, based on the data on this page

What is Norethynodrel?

Norethynodrel is an oxo steroid.

What is the CAS number of Norethynodrel?

The CAS registry number of Norethynodrel is 68-23-5.

What is the molecular formula and weight of Norethynodrel?

The molecular formula of Norethynodrel is C20H26O2 and its molar mass is 298.43 g/mol.

What is Norethynodrel used for?

Therapeutic category: Progestogen. In combination with estrogen as contraceptive (oral) (Former). Use classes: Pharmaceuticals.

Is Norethynodrel hazardous?

Norethynodrel carries the GHS signal word "Danger". Main hazards: may cause cancer, may damage fertility or the unborn child. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Norethynodrel?

Norethynodrel is usually classified under HS code 293723 (Oestrogens and progestogens). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Norethynodrel?

CompoundList lists 15 suppliers of Norethynodrel in United States, China, Canada, Czech Republic and 2 more. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

What is the price of Norethynodrel?

Suppliers quote Norethynodrel on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Norethynodrel

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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