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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)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
State
State

At room temperature, norethisterone is in a solid state.

Melting point (Celsius)
203.00
Melting point (Kelvin)
476.15
Boiling point (Celsius)
437.50
Boiling point (Kelvin)
710.65
General information
Molecular weight
298.42g/mol
Molar mass
298.4190g/mol
Density
1.1100g/cm3
Appearence

Norethisterone is typically a white to creamy white, crystalline powder.

Comment on solubility

Solubility of (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 (C20H26O2)

When considering the solubility of the compound (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 with the chemical formula C20H26O2, several important factors come into play:

  • Polarity: The presence of hydroxyl (-OH) groups typically indicates some level of polarity, potentially leading to higher solubility in polar solvents such as water. However, the hydrocarbon structure of the molecule would suggest limited solubility in highly polar environments.
  • Solvent Compatibility: This compound is more likely to be soluble in organic solvents, including ethyl acetate, methanol, or ethanol, due to its diverse hydrocarbon framework.
  • Temperature Influence: As with many organic compounds, solubility may increase with temperature; thus, heating solvents can enhance the dissolution process.
  • pH Sensitivity: The solubility might also depend on the pH of the solution, wherein alterations in pH could affect the ionization state of the compound.

In summary, the solubility of C20H26O2 is expected to be favorable in organic solvents while being less soluble or practically insoluble in water due to its complex structure comprising both hydrophobic and hydrophilic components. As the saying goes, "like dissolves like," and this compound epitomizes that principle well.

Interesting facts

Interesting Facts about (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

This compound, with its intricate structure and specific stereochemistry, is a prime example of the fascinating world of steroid derivatives. Its unique attributes provide valuable insights into both pharmacological applications and chemical synthesis.

Key Features:

  • Stereochemical Complexity: The designation of multiple stereocenters indicated by the R and S configurations points to the compound's potential for exhibiting varying biological activities based on its three-dimensional orientation.
  • Ethynyl Substitution: The presence of an ethynyl group suggests potential reactivity and biosynthetic pathways, making it an interesting target for medicinal chemistry.
  • Hydroxyl Group Influence: The hydroxy group at the 17th position can significantly affect the compound's solubility, reactivity, and interactions with biological systems, such as hormone receptors.
  • Natural Product Analogs: Its structural features bear resemblance to natural steroids, paving the way for research into therapeutic compounds that could mimic or modify steroid-like actions.

As you delve into the chemistry of this compound, remember:

"The intricacy of nature’s compounds often reflects untold stories of evolution and biological function."

This compound is not only a marvel of chemical architecture but also represents the potential for further developments in drug design and synthesis methodologies. Hence, studying such compounds can open doors to new therapeutic avenues in treating various health conditions.

Synonyms
norethindrone
Norethisterone
68-22-4
Norethisteron
Micronor
19-Norethisterone
Norlutin
Anovule
Camila
Gestest
Noriday
Utovlan
Primolut-N
Micronovum
Norethynodrone
Conludag
Norcolut
Norluten
Triella
Mini-pill
Noresthisterone
Norethisteronum
Norethyndron
Noretisterona
Conludaf
Micronett
Mini-Pe
Noralutin
Norgestin
Norluton
Proluteasi
Norfor
Utovlar
Norpregneninlone
Norpregneninolone
19-Nor-ethindrone
Nor-QD
Ethinylnortestosterone
Norethynodron
Anovulatorio
Ciclovulan
Estrinor
Microneth
Norethadrone
Synphase
Genora
Nelova
Nodiol
Milli
Noraethisteronum
Norpregneninotone
Ethynylnortestosterone
17alpha-Ethynyl-19-nortestosterone
Synphasic 28
Brevinor 21
Brevinor 28
Trinovum 21
Errin
Menzol
Noriday 28
19-Nor-17alpha-ethynyltestosterone
Jenest-28
Ethynylmortestosterone
Brevinor-1 21
Brevinor-1 28
Ovysmen 1 35
Ortho-Novum 1 35
Ortho-Novum 1 50
Anhydrohydroxynorprogesterone
Noretisterone
Ortho-Novum 7 7 7
Ovysmen 0.5 35
Ortho 1 35
19-Norethinyltestosterone
Ortho 7 7 7
17alpha-Ethinyl-19-nortestosterone
Primolut N
Minovlar
17alpha-Ethynyl-4-estren-17-ol-3-one
19-Nor-17-ethinyltestosterone
17-alpha-Ethynyl-19-nortestosterone
19-Nor-17-alpha-ethynyltestosterone
Ethinyl-19-nortestosterone
Normapause
17alpha-Ethinylestra-4-en-17beta-ol-3-one
Norethisteronum [INN-Latin]
Noretisterona [INN-Spanish]
NSC-9564
17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one
17beta-Hydroxy-19-norpregn-4-en-20-yn-3-one
17-alpha-Ethynyl-4-estren-17-ol-3-one
19-Norethindrone
19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one
17alpha-Ethynyl-17-hydroxy-4-estren-3-one
19-Nor-17alpa-ethynyltestosterone
Norethindrone (USP)
19-nor-17alpha-Ethynylandrosten-17beta-ol-3-one
CCRIS 484
4-Estren-17alpha-ethynyl-17beta-ol-3-one
17alpha-Ethynyl-19-norandrost-4-en-17beta-ol-3-one
Activella
N.E.E.
17-alpha-Ethynyl-17-hydroxy-4-estren-3-one
SC 4640
HSDB 3370
17alpha-Ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one
17-beta-Hydroxy-19-norpregn-4-en-20-yn-3-one
19-Nortestosterone, 17-ethynyl-
Nor-Q.D.
17-ethynyl-17beta-hydroxyestr-4-en-3-one
19-Nor-17-alpha-ethynylandrosten-17-beta-ol-3-one
EINECS 200-681-6
17-alpha-Ethynyl-19-norandrost-4-en-17-beta-ol-3-one
17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one
UNII-T18F433X4S
19-Nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one
BRN 1915671
CHEBI:7627
Norethindrone [USP]
DTXSID9023380
Norethisterone [INN]
AI3-26422
17alpha-Ethynyl-19-nor-4-androsten-17beta-ol-3-one
T18F433X4S
(17-alpha)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one
Norethindrone (Standard)
17-alpha-Ethinylestra-4-en-17-beta-ol-3-one
Gencept
Norethin
Estr-4-en-3-one, 17alpha-ethynyl-17-hydroxy-
SC-4640
CHEMBL1162
Combipatch
Norcept-E
MLS001163874
17-alpha-19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-
19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-
DTXCID303380
17-alpha-Ethynyl-17-beta-hydroxy-19-norandrost-4-en-3-one
EC 200-681-6
Tri-Norinyl
Noretisterone [DCIT]
NORINYL COMPONENT NORETHINDRONE
VYFEMLA COMPONENT NORETHINDRONE
ARANELLE COMPONENT NORETHINDRONE
BREVICON COMPONENT NORETHINDRONE
TAYTULLA COMPONENT NORETHINDRONE
(17alpha)-17-hydroxy-19-norpregn-4-en-20-yn-3-one
(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
FEMCON FE COMPONENT NORETHINDRONE
19-Nor-17-alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-
NORQUEST FE COMPONENT NORETHINDRONE
(17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one
LO MINASTRIN FE COMPONENT NORETHINDRONE
MINASTRIN 24 FE COMPONENT NORETHINDRONE
17alpha-hydroxy-19-norpregn-4-en-20-yn-3-one
Norethisteronum (INN-Latin)
Noretisterona (INN-Spanish)
Nora-BE
Norethisterone [Progestins]
NORETHINDRONE (USP-RS)
NORETHINDRONE [USP-RS]
NORETHISTERONE (MART.)
NORETHISTERONE [MART.]
(14beta,17alpha)-17-Ethynyl-17-Hydroxyestr-4-En-3-One
Norethindirone
17-Ethinyl-19-nortestosterone
NORETHINDRONE (USP IMPURITY)
NORETHINDRONE [USP IMPURITY]
NORETHISTERONE (EP IMPURITY)
NORETHISTERONE [EP IMPURITY]
NORETHINDRONE (USP MONOGRAPH)
NORETHINDRONE [USP MONOGRAPH]
Micronor (TN)
SMR000499579
norethisterone (norethindrone)
Primolut-N (TN)
Camila (TN)
19-Nor-17-ethinyl testosterone
LEVONORGESTREL IMPURITY U (EP IMPURITY)
LEVONORGESTREL IMPURITY U [EP IMPURITY]
19-Nor-ethinyl--4,5-testosterone
Norethindrone (Norethisterone)
Affodel
Deblitane
Heather
Incassia
Jencycla
Norlyda
Norlyroc
Sharobel
Emzahh
Tulana
Lyleq
19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17.alpha.)-
Lyza
Nora Be
CAS-68-22-4
NCGC00094738-01
ENT
NET
Prestwick_646
17alpha-Ethinyl-17beta-hydroxy-delta(sup:4)-estren-3-one
17-alpha-Ethinyl-17-beta-hydroxy-delta(sup:4)-estren-3-one
Norethisterone (JP17)
Prestwick0_000253
Prestwick1_000253
Prestwick2_000253
Prestwick3_000253
NORETHINDRONE [MI]
NORETHINDRONE [HSDB]
NORETHISTERONE [JAN]
SCHEMBL23390
BSPBio_000066
NORETHINDRONE [VANDF]
MLS001076679
SPBio_002285
BPBio1_000074
GTPL2880
17-Ethynyl-19-Nortestosterone
NORETHISTERONE [WHO-DD]
NORETHISTERONE [WHO-IP]
17-Ethinyl-19-nor-testosterone
HY-B0554R
HMS1568D08
HMS2090D21
HMS2095D08
HMS2231E18
HMS3259C16
HMS3712D08
NORETHINDRONE [ORANGE BOOK]
BCP28306
HY-B0554
17alpha-pregn-4-en-20-yn-3-one
Tox21_111322
Tox21_302427
19-Norethindrone, >=98%, powder
BDBM50148732
LMST02030097
MFCD00067596
s4040
AKOS005267172
NORETHISTERONUM [WHO-IP LATIN]
Tox21_111322_1
CCG-220253
DB00717
FN26442
NC00576
NCGC00179669-01
NCGC00179669-02
NCGC00179669-04
NCGC00255187-01
AC-11100
AC-33117
AS-56451
CPD000499579
NORETHINDRONE COMPONENT OF ARANELLE
17alpha-Ethynyl-17-hydroxyest-4-en-3-one
17alpha-Ethynyl-3-oxo-4-estren-17beta-ol
NORETHINDRONE COMPONENT OF FEMCON FE
CS-0694821
N0449
NORETHINDRONE COMPONENT OF NORQUEST FE
NS00009098
17alpha-ethynyl-17-hydroxy-Estr-4-en-3-one
Norethisterone 100 microg/mL in Acetonitrile
C05028
C76161
D00182
17alpha-Ethynyl-17beta-hydroxyestr-4-en-3-one
17beta-Hydroxy-17alpha-ethynylestr-4-en-3-one
17-alpha-Ethynyl-17-beta-hydroxy-4-estren-3-one
Q421352
SR-01000765382
17alpha-Ethinyl-17alpha-Ethinyl-19-nortestosterone
SR-01000765382-3
13-methyl-17alpha-ethynyl-17-hydroxygon-4-en-3-one
17-Hydroxy-17-alpha-19-norpregn-4-en-20-yn-3-one
17-Hydroxy-19-nor-17alpha-4-pregnen-20-yn-3-one
17-hydroxy-19-nor-17alpha-pregn-4-en-20yn-3-one
19-Nor-17alpha-ethynyl-4-androsten-17beta-ol-3-one
19-Norethindrone, VETRANAL(TM), analytical standard
BRD-K92073408-001-03-3
BRD-K92073408-001-16-5
NORETHISTERONE ACETATE IMPURITY A [EP IMPURITY]
17-Hydroxy-(17alpha)-19-Norpregn-4-en-20-yn-3-one
17alpha-Ethynyl-19-norandro-st-4-en-17beta-ol-3-one
17-Ethynyl-17-hydroxyestr-4-en-3-one (ACD/Name 4.0)
17alpha-Ethynyl-17beta-hydroxy-19-nor-4-androsten-3-one
Norethisterone, British Pharmacopoeia (BP) Reference Standard
Norethisterone, European Pharmacopoeia (EP) Reference Standard
Norethindrone, United States Pharmacopeia (USP) Reference Standard
17-Hydroxy-19-nor-17?-pregn-4-en-20-yn-3-one;17?-Ethynyl-19-nortestosterone
Norethisterone for system suitability, European Pharmacopoeia (EP) Reference Standard
(8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
200-681-6
Norethindrone (Norethisterone), Pharmaceutical Secondary Standard; Certified Reference Material