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Norethisterone

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Identification
Molecular formula
C20H26O2
CAS number
68-22-4
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
State
State

At room temperature, norethisterone is generally in a solid state. Due to its pharmaceutical applications, it is commonly formulated in tablets or other solid dosage forms.

Melting point (Celsius)
204.00
Melting point (Kelvin)
477.15
Boiling point (Celsius)
390.00
Boiling point (Kelvin)
663.15
General information
Molecular weight
298.42g/mol
Molar mass
298.4190g/mol
Density
1.1300g/cm3
Appearence

Norethisterone typically appears as a white or almost white crystalline powder. It is odorless or may have a slight distinctive odor. The powder may clump together due to its crystalline nature.

Comment on solubility

Solubility of (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 (C20H26O2)

The solubility of the compound C20H26O2, known as (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, can be influenced by various factors. Given its molecular structure, several considerations come into play:

  • Polarity: The presence of hydroxyl groups can contribute to a degree of polarity, which may enhance solubility in polar solvents such as water and alcohols.
  • Hydrophobic Character: The large hydrocarbon framework in the compound suggests strong hydrophobic interactions, potentially reducing solubility in aqueous environments.
  • Solvent Choice: This compound is likely to have improved solubility in organic solvents like ethanol, acetone, or chloroform, due to their compatibility with the hydrophobic segments of the molecule.

In summary, the solubility of C20H26O2 can be characterized by a balance of its hydrophilic and hydrophobic properties, indicating that while it may dissolve in certain polar solvents, it potentially performs better in non-polar or mildly polar solvents. This nuanced behavior underlines the importance of selecting the right solvent for optimal solubility.

Interesting facts

Interesting Facts About (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

This complex organic compound belongs to a class of chemicals that has garnered interest primarily due to its structural intricacies and potential biological activities. Here are some notable points about this fascinating compound:

  • Structural Complexity: The compound features a detailed steroid-like structure, characterized by multiple stereocenters which lend it unique three-dimensional properties.
  • Functional Groups: The presence of ethynyl and hydroxyl functional groups suggests reactivity that could be exploited in organic synthesis and potential medicinal chemistry applications.
  • Stereochemistry: With specific stereoconfigurations (8R, 9S, 13S, 14S, 17R), understanding the stereochemistry is crucial as it often influences the biological activity of compounds. This could have implications in drug design and development.
  • Biological Potential: Many compounds with similar structures have been studied for their possible roles as hormones or hormone modulators. This opens a dialogue about its effects on human health and potential therapeutic applications.
  • Research Interest: Ongoing research in the field of medicinal chemistry may utilize this compound as a lead structure for synthesizing new pharmaceuticals targeting various diseases.

As a chemistry student or scientist, delving into the properties and potential applications of such compounds can lead to groundbreaking discoveries in the realm of biochemistry and pharmacology. As quoted in the field, "The essence of discovery lies in the pursuit of understanding structure-function relationships in complex organic compounds."

In conclusion, the diversity and complexity encapsulated within (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 make it an intriguing subject of study for both theoretical exploration and practical applications.

Synonyms
norethynodrel
Noretynodrel
68-23-5
Norethinodrel
Enidrel
Lynestrol
19-Norethynodrel
SC-4642
Norethinynodrel
Norethynodral
Noretinodrel
NSC-15432
17-Ethinyl-5(10)-estraeneolone
Noretynodrel [INN]
Noretynodrelum [INN-Latin]
CCRIS 486
HSDB 2951
17alpha-Ethinyl-5,10-estrenolone
Norethynodrel [USAN:USP]
19-Nor-ethinyl-5,10-testosterone
EINECS 200-682-1
17-alpha-Ethinyl-5,10-estrenolone
NSC 15432
CB 8023
BRN 2389771
Noretynodrel (INN)
MLS000069824
DTXSID3021069
Norethynodrel (USAN)
88181ACA0M
17-Hydroxy-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one
17alpha-Ethynyl-5(10)-estren-17-ol-3-one
17alpha-Ethinyl-5(10)estraen-17beta-ol-3-one
NORETHYNODREL [MI]
17alpha-Ethynyl-estr-5(10)-en-3-on-17beta-ol
19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-, (17alpha)-
17-alpha-Ethynyl-17-hydroxyestr-5(10)-en-3-one
NORETHYNODREL [HSDB]
NORETHYNODREL [USAN]
17alpha-Ethinyl-delta(sup)-5,10-19-nortestosterone
17alpha-Ethynyl-17beta-hydroxyestr-5(10)-en-3-one
NORETHYNODREL [VANDF]
NORETYNODREL [MART.]
Estr-5(10)-en-3-one, 17alpha-ethynyl-17-hydroxy-
DTXCID60563
NORETYNODREL [WHO-DD]
17-alpha-Ethinyl-delta(super)-5,10-19-nortestosterone
(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-Hydroxy(17alpha)-19-norpregn-5(10)-en-20-yn-3-one
17alpha-Ethynyl-19-nor-5(10)-androsten-17beta-ol-3-one
17-alpha-Ethynyl-19-nor-5(10)-androsten-17-beta-ol-3-one
19-Nor-17alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-
CHEBI:34895
17alpha-Ethinyl-17beta-hydroxy-delta(sup 5(10))-estren-3-one
17alpha-Ethinyl-19-nor-delta-5(10)-androstene-17beta-ol-3one
17alpha-Ethynyl-17beta-hydroxy-3-oxo-delta(sup 5(10))-estrene
17alpha-Ethynyl-17beta-hydroxy-delta(sup 5(10))-estren-3-one
19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-, (17.alpha.)-
NORETHYNODREL [ORANGE BOOK]
NSC15432
NORETHYNODREL [USP IMPURITY]
ENOVID COMPONENT NORETHYNODREL
13-Methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16,17-tetradecahydro-15H-cyclopenta(a)-phenanthrene-3-one
SMR000058915
19-Nor-17-alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-
Norethynodrel (>90%)
NORETHISTERONE IMPURITY D [EP IMPURITY]
Norethynodrel (USAN:USP)
Noretynodrelum (INN-Latin)
NORETYNODREL (MART.)
(17beta-ethynyl-17-hydroxyestr-5(10)-en-3-one
(17beta)-17-ethynyl-17-hydroxyestr-5(10)-en-3-one
Noretinodrel [DCIT]
Noretynodrelum
NORETHYNODREL (USP IMPURITY)
(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
13-METHYL-17-ETHYNYL-17-HYDROXY-1,2,3,4,6,7,8,9,11,12,13,14,16,17-TETRADECAHYDRO-15H-CYCLOPENTA(A)PHENANTHREN-3-ONE
NORETHISTERONE IMPURITY D (EP IMPURITY)
Norethynodrel [Progestins]
17-Hydroxy-19-nor-17.alpha.-pregn-5(10)-en-20-yn-3-one
UNII-88181ACA0M
17-alpha-Ethynyl-5(10)-estren-17-ol-3-one
CAS-68-23-5
NCGC00016304-01
(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
Prestwick_883
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
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
Opera_ID_1052
Prestwick0_000024
Prestwick1_000024
Prestwick2_000024
Prestwick3_000024
17-.alpha.-Ethynyl-17-hydroxyestr-5(10)-en-3-one
17.alpha.-Ethinyl-.DELTA.5(10)-19-nortestosterone
17-.alpha.-Ethinyl-.DELTA.5(10)-19-nortestosterone
17.alpha.-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one
5(10)-Estren-3-one, 17alpha-ethynyl-17beta-hydroxy-
17.alpha.-Ethinyl-.delta.(sup)-5,10-19-nortestosterone
CHEMBL1387
SCHEMBL37838
BSPBio_000087
17-.alpha.-Ethynyl-17-.beta.-hydroxy-5(10)-estren-3-one
17-.beta.-Hydroxy-17-.alpha.-ethinyl-5(10)-estren-3-one
BIDD:ER0192
SPBio_002008
(17-.alpha.)-17-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one
17-.alpha.-Ethynyl-17-.beta.-hydroxy-.DELTA.5(10)-estren-3-one
17.alpha.-Ethinyl-17.beta.-hydroxy-.DELTA.5(10)-estren-3-one
17.alpha.-Ethynyl-17.beta.-hydroxy-.DELTA.5(10)-estren-3-one
17.alpha.-Ethynyl-17.beta.-hydroxy-3-oxo-.DELTA.5(10)-estrene
BPBio1_000097
17-Ethynyl-17-hydroxyestr-.DELTA.5(10)-en-3-one, (17.alpha.,17.beta.)-
HMS1568E09
HMS2095E09
HMS2232J10
HMS3712E09
HY-B1341
Tox21_110359
BDBM50410507
AKOS026749810
CCG-220024
DB09371
FN26448
NORETHYNODREL COMPONENT OF ENOVID
NCGC00179666-01
17-ALPHA-ETHINYLS-5,10-ESTRENOLONE
CS-0013090
NS00006110
D05207
G89723
WLN: L E5 B666OV MUTJ E1 F1UU1 QQ
EN300-7481217
SR-01000721945
Q5659069
SR-01000721945-2
BRD-K80334323-001-03-5
Estr-5(10)-en-3-one,17.alpha.-ethynyl-17-hydroxy-
17-ALPHA-ETHYNYL-17-HYDROXY-5(10)-ESTREN-3-ONE
17-ALPHA-ETHYNYLESTR-5(10)-EN-17-BETA-OL-3-ONE
17-hydroxy-19-nor-17alpha-pregn-5(10)en-20-yn-3-one
17-Hydroxy(17-alpha)-19-norpregn-5(10)-en-20-yn-3-one
17-Hydroxy-19-nor-17-alpha-pregn-5(10)-en-20-yn-3-one
17-ALPHA-ETHYNYL-17-BETA-HYDROXYESTER-5(10)-EN-3-ONE
17-ALPHA-ETHYNYL-19-NOR-S(10)-ANDROSTEN-17-BETA-OL-3-ONE
19-Nor-17alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-(8CI)
13-METHYL-17-ETHYNYL-17-HYDROXY-1,2,3,4,6,7,8,9,11,12,1 3,14,16,17-TETRADECAHYDRO-15H-CYCLOPENTA
13-Methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16 ,17-tetradecahydro-15H-cyclopenta[a]phenanthren-3-one;17-Hydroxy-19-nor- 17?-pregn-5(10)-en-20-yn-3-one;(17?)-17-hydroxy-19-norpregn-5(10)-en-20- yn-3-one
200-682-1