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Norethisterone

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Identification
Molecular formula
C20H26O2
CAS number
68-22-4
IUPAC name
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one;(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
State
State
Norethisterone is typically found as a solid at room temperature.
Melting point (Celsius)
204.20
Melting point (Kelvin)
477.35
Boiling point (Celsius)
453.15
Boiling point (Kelvin)
726.30
General information
Molecular weight
298.42g/mol
Molar mass
298.4240g/mol
Density
1.1951g/cm3
Appearence

Norethisterone, also known as norethindrone, typically appears as a white or almost white crystalline powder. It is practically insoluble in water, sparingly soluble in ethanol (96 per cent), and soluble in methylene chloride. It is sensitive to light.

Comment on solubility

Solubility Overview

The solubility of organic compounds, particularly those with complex structures like (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one and (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol, can often be influenced by several factors:

  • Polarity: The presence of functional groups, such as hydroxyl (-OH) and ethynyl (-C≡CH), may suggest some degree of polarity, which could enhance solubility in polar solvents like water or alcohol.
  • Molecular Structure: The overall size and shape of these compounds might hinder their solubility in certain solvents. A bulky structure can lead to decreased solubility in polar solvents.
  • Hydrophobic Interactions: The dodecahydro and octahydro regions indicate significant hydrophobic character, likely resulting in low solubility in water while being more soluble in organic solvents like hexane or dichloromethane.
  • Temperature and pH: Solubility is also temperature-dependent, with higher temperatures generally increasing solubility. Additionally, pH can play a role if the compound can ionize under varying conditions.

In conclusion, while the specific solubility characteristics of these compounds require empirical testing for confirmation, we can anticipate:

  • Better solubility in organic solvents due to their hydrophobic traits.
  • A potentially reduced solubility in water, especially at room temperature.
  • Increased solubility at elevated temperatures or when mixed with compatible solvents.

To truly uncover the solubility profile, experimental results remain the most conclusive guide.

Interesting facts

Interesting Facts About the Compound

This compound, a complex polycyclic structure, belongs to the class of steroid derivatives and showcases intriguing characteristics that make it a subject of extensive study in the fields of chemistry and pharmacology. Here are some key highlights:

  • Unique Stereochemistry: The compound exhibits a distinct stereochemistry with multiple chiral centers, denoted by the (8R, 9S, 10R, 13S, 14S, 17R) configurations. This spatial arrangement of atoms is crucial as it influences the biological activity and interactions of the molecule.
  • Applications in Medicine: Derivatives of this compound are often researched for their therapeutic potential. Many compounds similar to these have been studied for their effectiveness as hormonal therapies or anti-cancer agents.
  • Role of Functional Groups: The presence of ethynyl and hydroxyl groups in the structure enhances the reactivity of the compound, making it possible to engage in various chemical reactions that further expand its utility in synthetic organic chemistry.
  • Natural Occurrence: Compounds with structural similarities are often found in nature. They may be derived from natural sources such as plants and animals, which have historically been tapped for their medicinal properties.
  • Synthetic Pathways: The synthesis of such complex molecules can be quite challenging. Chemists employ various organic synthesis techniques, including multi-step reactions and carefully controlled conditions to obtain the desired stereochemical outcomes.
  • Research Opportunities: Given its complex nature, this compound represents a fantastic opportunity for research in asymmetric synthesis, medicinal chemistry, and drug development. Scientists continually seek to unlock new pathways that could lead to more effective and selective therapeutic agents.

In summary, the intricate structure and important functional groups within this compound underscore its significance in both the laboratory and potential therapeutic applications. As the field of chemistry evolves, ongoing research will likely reveal even more fascinating insights about this and similar compounds.

Synonyms
Low-ogestrel
Norgestrel and Ethinyl Estradiol
CRYSELLE
LOW-OGESTREL-21
LOW-OGESTREL-28
LO/OVRAL-28
OVRAL-28
Elinest
OGESTREL 0.5/50-21
OGESTREL 0.5/50-28
TURQOZ
Ethinyl estradiol; norgestrel
ethinylestradiol & levonorgestrel
ETHINYL ESTRADIOL/NORGESTREL
ETHINYL ESTRADIOL;NORGESTREL
NORGESTREL/ETHINYL ESTRADIOL
NORGESTREL;ETHINYL ESTRADIOL
ETHINYL ESTRADIOL / NORGESTREL
NORGESTREL / ETHINYL ESTRADIOL
ethinylestradiol + levonorgestrel
ethinylestradiol / levonorgestrel
ethinylestradiol and levonorgestrel
lo/ovral
Ovral
Microgynon
39366-37-5
Trikvilar
Elifemme
8056-51-7
Minisiston
Trinordiol
Anteovin
Eugynon
Gravistat
Rigevidon
Sequostat
Stediril
Trigynon
Triquilar
Trisiston
Adepal
Ovidon
Biphasil
Duoluton
Femenal
Follimin
Follinett
Follinyl
Gynatrol
Logynon
Minidril
Minigynon
Neogynon
Neovlar
Neovletta
Nordiol
Orasecron
Ovranett
Primovlar
Quasense
Sequilar
Sequilarum
Alesse
Ediwal
Levora
Lybrel
Ovran
Anna
Pro-Duosterone
Lo-Femenal
Stediril D
Tri-Regol
Microgynon 30
Ovral L
Microvlar 30
Triphasil-21
Biphasil 21
Biphasil 28
Stederil 30
Schering PC 4
Eugynon 30
Nordiol-28
Alesse 28
LEVLITE
Ovral 21
Ovral 28
aviane
Loseasonique
Altavera
Introvale
Jolessa
Levonest
Marlissa
PC 4 (contraceptive)
Quartette
Portia
Sronyx
Norgestrel-ethinyl estradiol
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one;(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
LOC 31A
Aviane-21Fe
SHB 261AB
SHB 264AB
CCRIS 7261
Ethinyl estradiol/levonorgestrel
Levonorgestrel/ethinyl estradiol
LOC 31
WL 33
WY-E 104
TRIPHASIL-28
ETHINYL ESTRADIOL-NORGESTREL COMBINATION
Levonorgestrel and Ethinyl Estradiol
ENPRESSE-21
ENPRESSE-28
NORDETTE-21
NORDETTE-28
LESSINA-21
LESSINA-28
TRIVORA-21
TRIVORA-28
AVIANE-21
AVIANE-28
PORTIA-21
PORTIA-28
aless
SH 71121
Twirla
Vienva
Levonorgestrel, ethinyl estradiol
Norgestrel-ethynylestradiol mixt.
SH D00264A
Levonorgestrel-ethinyl estradiol mixt.
LEVORA 0.15/30-21
LEVORA 0.15/30-28
Ethinylestradiol - levonorgestrel mixt.
Levonorgestrel - ethynylestradiol mixt.
PREVEN EMERGENCY CONTRACEPTIVE KIT
AG 200-15
Levonorgestrel and Ethinyl Estradiol tablets
SCHEMBL4451192
DTXSID90192569
AKOS040751734
18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-(+-)-, mixt. with (17-alpha)-19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol
18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-, mixt. with (17-alpha)-19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol
AG200-15
ethinyl estradiol, levonorgestrel drug combination