1. APIs
  2. Levonorgestrel
  3. Impurities
  4. 3-Deoxolevonorgestrel

3-Deoxolevonorgestrel

Structure

MOL SDF CML

Other Names & Identifiers

  • BP Levonorgestrel Impurity D
  • 13-ethyl-18,19-dinor-17α-pregn-4-en-20-yn-17-ol
  • 17α-ethinyl-13-ethyl-4-gonene-17-ol

CASRN

32419-58-2

Reaxys ID Number

2565263

References

Molecular Formula

C21H30O

References

Structural Difference from API

missing carbonyl at C3

References

Source of Impurity

Synthetic side product formed during the Birch reduction steporiginating from a side product of the Birch reduction step in the synthesis of norgestrel (ref = Hovrath, 1997, Gorog 1998); over-reduction of phenolic ring A in the Birch reduction step of the synthesis (ref = Gorog, 1998)

library_books

References

  1. Görög, S.; Babják, M.; Balogh, G.; Brlik, J.; Dravecz, F.; Gazdag, M.; Horváth, P.; Laukó, A.; Varga, K. Estimation of impurity profiles of drugs and related materials Part 19: Theme with variations. Identification of impurities in 3-oxosteroids. Journal of Pharmaceutical and Biomedical Analysis.1998, 18 (4), 511–525. 1998; 18:511-25.
    2. (View all citations for this reference)
  2. Horvath PB, G.; Brlik, J.; Csehi, A.; Dravecz, F.; Halmos, Z.; Lauko, A.; Renyei, M.; Varga, K.; Gorog, S. Estimation of impurity profiles of drugs and related materials .16. Identification of the side-products of the ethinylation step in the synthesis of contraceptive gestogens. Journal of Pharmaceutical and Biomedical Analysis. 1997; 15:1343-9.
    3. (View all citations for this reference)

Molecular Weight

298.47 g/mol

References

Melting Point

107-108° C in methanol

library_books

References

  1. Online Subscription Database. Reed Elsevier Properties SA. (View all citations for this reference)
  2. Smith HP, P. C.; Smith, L. L.; Gadsby, B.; Hartley, D.; Ledig, K.; Herbst, D.; Wendt, G. R.; Fisher, J.; Pattison, T. W.; Watson, D. H. P.; Siddall, J.; McLoughlin, B. J.; Tokolics, J.; Siuda, J.; Rees, R.; McMenamin, J.; Douglas, G. H.; Foell, T.; Edgren, R. A.; Buzby, G. C.; Jansen, A. B. A.; Hughes, G. A. Totally synthetic steroid hormones. 2. 13β-alkylgona-1,3,5(10)-trienes 13β-alkylgon-4-en-3-ones + related compounds. Journal of the Chemical Society. 1964:4472-&.
    3. (View all citations for this reference)

Pub Chem ID

29979853

References

Limits

0.1%

References

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