Skip to main content
SpringerLink
Log in

Adrenaline system: another rare case of conglomerate with partial solid solutions

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

Adrenaline, in its enantiomeric form l-, is the drug of choice for the treatment of cardiac arrest or certain serious shock conditions. However, although its crystal structure is known, there are no thermodynamic data on this molecule. Regarding the racemic form of this molecule, the latter has never been characterized either from a thermodynamic or crystallographic point of view. The melting characteristics, temperature and enthalpy of both the enantiomer and the racemate of adrenaline were determined using the plateau values obtained at high DSC scan rates. The refinement of the RX diffraction pattern of the racemate revealed that this equimolar mixture was a conglomerate with partial solid solutions. This conclusion was supported by the phase diagram between the two enantiomers established from the l-enantiomer and the racemate where the results presented in this paper show that a lower solid-state miscibility exists between the two enantiomers. The equimolar compound is therefore part of the very limited series of conglomerate with partial miscibility.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Andersen AM. Structural studies of metabolic products of dopamine. III. Crystal and molecular structure of (−)-adrenaline. Acta Chem Scand. 1975;B29:239–44.

    Article  CAS  Google Scholar 

  2. Bannach G, Cervini P, Gomes Cavalheiro ET, Ionashiro M. Using thermal and spectroscopic data to investigate the thermal behavior of epinephrine. Thermochim Acta. 2010;499:123–7.

    Article  CAS  Google Scholar 

  3. Mitchell CR, Bao Y, Benz NJ, Zhang S. Comparison of the sensitivity of evaporative universal detectors and LC/MS in the HILIC and the reversed-phase HPLC modes. J Chromatogr B. 2009;877:4133–9.

    Article  CAS  Google Scholar 

  4. Corvis Y, Menet MC, Négrier P, Espeau P. The role of stearic acid in ascorbic acid protection from degradation: heterogeneous system for homogeneous thermodynamic data. New J Chem. 2013;37:761–8.

    Article  CAS  Google Scholar 

  5. Rosa F, Négrier P, Corvis Y, Espeau P. Crystal structure determination and thermal behavior upon melting of p-synephrine. Thermochim Acta. 2016;632:18–22.

    Article  CAS  Google Scholar 

  6. Wermester N, Aubin E, Pauchet M, Coste S, Coquerel G. Preferential crystallization in an unusual case of conglomerate with partial solid solutions. Tetrahedron Asymmetry. 2007;18:821–31.

    Article  CAS  Google Scholar 

  7. Renou L, Morelli T, Coste S, Petit MN, Berton B, Malandain JJ, Coquerel G. Chiral discrimination at the solid state of methyl 2-[diphenylmethylsulfinyl]acetate. Cryst Growth Des. 2007;7:1599–607.

    Article  CAS  Google Scholar 

  8. Kaemmere H, Lorenz H, Black SN, Seidel-Morgenstern A. Study of system thermodynamics and the feasibility of chiral resolution of the polymorphic system of malic acid enantiomers and its partial solid solutions. Cryst Growth Des. 2009;9:1851–62.

    Article  CAS  Google Scholar 

  9. Bredikhin AA, Zakharychev DV, Gubaidullin AT, Fayzullin RR, Pashagin AV, Bredikhina ZA. Crystallization features of the chiral drug timolol precursor: the rare case of conglomerate with partial solid solutions. Cryst Growth Des. 2014;14:1676–83.

    Article  CAS  Google Scholar 

  10. Taratin NV, Lorenz H, Kotelnikova EN, Glikin AE, Galland A, Dupray V, Coquerel G, Seidel-Morgenstern A. Mixed crystals in chiral organic systems: a case study on (R)- and (S)-ethanolammonium 3-chloromandelate. Cryst Growth Des. 2012;12:5882–8.

    Article  CAS  Google Scholar 

  11. Kehl T, van der Plaats G. US Patent 5.033.866; 1991.

  12. Corvis Y, Négrier P, Espeau P. Physicochemical stability of solid dispersions of enantiomeric or racemic ibuprofen in stearic acid. J Pharm Sci. 2011;100:5235–43.

    Article  CAS  Google Scholar 

  13. Materials Studio Modeling 5.5. 2010. http://accelrys.com/products/collaborative-science/biovia-materials-studio/.

  14. Neumann MA. X-cell: a novel indexing algorithm for routine tasks and difficult cases. J Appl Cryst. 2003;36:356–65.

    Article  CAS  Google Scholar 

  15. Schröder I. Dependence of the solubility of a solid on its melting point. Z Phys Chem. 1893;11:449–65.

    Google Scholar 

  16. Van Laar JJ. Process of the fusion curves of firm alloys and amalgams. Arch Neerl. 1903;8:264–84.

    Google Scholar 

  17. Drebushchak VA, Kovalevskaya YA, Paukov IE, Boldyreva EV. Heat capacity of d- and dl-serine in a temperature range of 5.5 to 300 K. J Therm Anal Calorim. 2007;89:649–54.

    Article  CAS  Google Scholar 

  18. Paukov IE, Kovalevskaya YA, Boldyreva EV. Low-temperature thermodynamic properties of l-cysteine. J Therm Anal Calorim. 2008;93:423–8.

    Article  CAS  Google Scholar 

  19. Paukov IE, Kovalevskaya YA, Boldyreva EV. Low-temperature heat capacity of l- and dl-phenylglycines. J Therm Anal Calorim. 2012;108:1311–6.

    Article  CAS  Google Scholar 

  20. Paukov IE, Kovalevskaya YA, Boldyreva EV. Low-temperature thermodynamic properties of l- and dl-valines. J Therm Anal Calorim. 2013;111:905–10.

    Article  CAS  Google Scholar 

  21. Gheorghe D, Neacşu A, Contineanu I, Tănăsescu S, Perişanu S. A calorimetric study of l-, d- and dl-isomers of tryptophan. J Therm Anal Calorim. 2017;130:1145–52.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank Ms. K. Debbasch for her advice and language improvements on the manuscript.

Author information

Authors and Affiliations

  1. Chemical and Biological Technologies for Health (UTCBS), CNRS UMR8258, INSERM U1022, Paris Descartes University, Sorbonne-Paris-Cité, Chimie ParisTech, PSL Research University, School of Pharmacy, 4 avenue de l’Observatoire, 75006, Paris, France

    Veronica Ianno’ & Philippe Espeau

  2. Laboratoire Ondes et Matière d’Aquitaine, UMR CNRS 5798, Université de Bordeaux, 351 cours de la Libération, 33405, Talence Cedex, France

    Philippe Négrier

Authors
  1. Veronica Ianno’
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Philippe Négrier
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Philippe Espeau
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

Corresponding author

Correspondence to Philippe Espeau.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ianno’, V., Négrier, P. & Espeau, P. Adrenaline system: another rare case of conglomerate with partial solid solutions. J Therm Anal Calorim 138, 997–1002 (2019). https://doi.org/10.1007/s10973-019-08301-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-019-08301-w

Keywords

Search

Navigation