1. APIs
  2. Levonorgestrel
  3. Impurities
  4. Norethisterone

Norethisterone

Structure

MOL SDF CML

Other Names & Identifiers

  • BP Levonorgestrel Impurity U
  • Norethindrone
  • 17-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one

CASRN

68-22-4

Molecular Formula

C20H26O2

References

Molecular Weight

298.43 g/mol

References

Density

1.2 g/cm3

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References

  1. Reisch JZ, J.; Henkel, G.; Ekizgucer, N. Photochemical studies. 65. Investigations on the photostability of ethisterone and norethisterone and their crystal-structures. Monatshefte Fur Chemie. 1993; 124:1169-75.
    2. (View all citations for this reference)

Circular Dichroism

290-370 nm in dioxane

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References

  1. Baier HD, G.; Quinkert, G. TOTAL SYNTHESIS VON (-)-NORGESTREL. Helvetica Chimica Acta. 1985; 68:1054-68.
    2. (View all citations for this reference)

Optical Rotary Power

-25° at 589 nm, 20° C, 26° at 589 nm and 25° C in chloroform

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References

  1. Baier HD, G.; Quinkert, G. TOTAL SYNTHESIS VON (-)-NORGESTREL. Helvetica Chimica Acta. 1985; 68:1054-68.
    2. (View all citations for this reference)
  2. Siemann HJS, S. Steroids. 8. Synthesis of racemic and enantiomeric 19-norsteroids. Journal Fur Praktische Chemie. 1969; 311:671-&.
    3. (View all citations for this reference)

Spectra

NMR

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References

    2. (View all citations for this reference)
  2. Kartashov VSS, S. V.; Arzamastsev, A. P. C-13 NMR Spectroscopic Identification of Steroidal Drugs. 2. Hestagenic and Estrogenic Hormones. Khimiko-Farmatsevticheskii Zhurnal. 1992; 26:95-8.
    3. (View all citations for this reference)
  3. Sedee AGJV, Gmjb; Guijt, W.; Haasnoot, C. A. G. Assignment of the H-1 and C-13 nuclear magnetic-resonance spectra of norethisterone using two-dimensional nuclear magnetic-resonance spectroscopy. Journal of the Chemical Society-Perkin Transactions 2. 1984:1755-9.
    4. (View all citations for this reference)

Spectra

IR

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References

  1. Baier HD, G.; Quinkert, G. TOTAL SYNTHESIS VON (-)-NORGESTREL. Helvetica Chimica Acta. 1985; 68:1054-68.
    2. (View all citations for this reference)
  2. Visser TV, J. H. Structural information from OH-stretching vibrations. 7. The orientation of the hydroxyl in 17-ethynyl-17-hydroxy and 17-methyl-17-hydroxy steroids. Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 1983; 39:921-4.
    3. (View all citations for this reference)

Reaxys ID Number

1915671

References

Structural Difference from API

methyl instead of ethyl at C13

References

Appearance

white crystalline powder

References

Melting Point

202° C, 206-209.5° C, 203-204° C

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References

  1. Djerassi CM, L.; Rosenkranz, G.; Sondheimer, F. STEROIDS .54. SYNTHESIS OF 19-NOR-17-ALPHA-ETHYNYLTESTOSTERONE AND 19-NOR-17-ALPHA-METHYLTESTOSTERONE. Journal of the American Chemical Society. 1954; 76:4092-4.
    2. (View all citations for this reference)
  2. Perera SKD, W. A.; Fedor, L. R. Acid-catalyzed and base-catalyzed isomerization of androst-5-ene-3,17-dione and 17α-ethynyl-17β-hydroxy-5-estren-3-one. Journal of Organic Chemistry. 1980; 45:2816-21.
    3. (View all citations for this reference)
  3. Siemann HJS, S. Steroids. 8. Synthesis of racemic and enantiomeric 19-norsteroids. Journal Fur Praktische Chemie. 1969; 311:671-&.
    4. (View all citations for this reference)

Octanol Water Partition Coefficient (logP)

2.97

References

Water Solubility

7.04 mg/L at 25° C

References

Organic Solubility

25° C: 1 in 150 parts 95% ethanol, 1 in 5 parts pyridine, 1 IN 80 parts acetone, 1 IN 30 parts chloroform; Sparingly soluble in alcohol; soluble in chloroform and dioxane; slightly soluble in ether.

References

Specific Optical Rotation

-31.7 to -25 at 20° C/D in chloroform

References

Vapor Pressure

3.14x10-7 mm Hg at 25° C

References

Henry's Law Constant

5.80x10-10 atm-cu m/mol at 25° C

References

Limits

0.2%

Toxicities

LD50 Mouse oral 6 g/kg (ref = toxnet) ; Reasonably anticipated to be a human carcinogen (ref = toxnet)

References

  1. British Pharmacopoeia 2017: Levonorgestrel monograph.
    2. (View all citations for this reference)