Determination of the enantiomeric purity of epinephrine by HPLC with circular dichroism detection

References

• Görög, S.; Gazdag, M. Enantiomeric Derivatization for Biomedical Chromatography. J. Chromatogr. B Biomed. Sci. Appl. 1994, 659, 51–84.
   PubMed Web of Science ®Google Scholar
• Zsila, F. Electronic Circular Dichroism Spectroscopy. In Pharmaceutical Sciences Encyclopedia, John Wiley & Sons, Inc. New York, 2010.
   Google Scholar
• Bertucci, C.; Andrisano, V.; Cavrini, V.; Castiglioni, E. Reliable Assay of Extreme Enantiomeric Purity Values by a New Circular Dichroism Based HPLC Detection System. Chirality 2000, 12, 84–92.
   PubMed Web of Science ®Google Scholar
• Bertucci, C.; Tedesco, D. Advantages of Electronic Circular Dichroism Detection for the Stereochemical Analysis and Characterization of Drugs and Natural Products by Liquid Chromatography. J. Chromatogr. A 2012, 1269, 69–81.
   PubMed Web of Science ®Google Scholar
• Bossu’, E.; Cotichini, V.; Gostoli, G.; Farina, A. Determination of Optical Purity by Nonenantioselective LC Using CD Detection. J. Pharm. Biomed. Anal. 2001, 26, 837–848.
   PubMed Web of Science ®Google Scholar
• Bringmann, G.; Münchbach, M.; Feineis, D.; Messer, K.; Diem, S.; Herderich, M.; Clement, H. W.; Stichel-Gunkel, C.; Kuhn, W. Endogenous Alkaloids in Man: XXXVIII. “Chiral” and “achiral” Determination of the Neurotoxin TaClo (1-Trichloromethyl-1,2,3,4-Tetrahydro-B-Carboline) from Blood and Urine Samples by High-performance Liquid Chromatography–Electrospray Ionization Tandem Mass Spectrometry. J. Chromatogr. B 2002, 767, 321–332.
   PubMed Web of Science ®Google Scholar
• de Andrés, F.; Castañeda, G.; Ríos, Á. Achiral Liquid Chromatography with Circular Dichroism Detection for the Determination of Carnitine Enantiomers in Dietary Supplements and Pharmaceutical Formulations. J. Pharm. Biomed. Anal. 2010, 51, 478–483.
   PubMed Web of Science ®Google Scholar
• Gergely, A.; Szász, G.; Szentesi, A.; Gyimesi-Forrás, K.; Kökösi, J.; Szegvári, D.; Veress, G. Evaluation of CD Detection in an HPLC System for Analysis of DHEA and Related Steroids. Anal. Bioanal. Chem. 2006, 384, 1506–1510.
   PubMed Web of Science ®Google Scholar
• Jenkins, A. L.; Hedgepeth, W. A. Analysis of Chiral Pharmaceuticals Using HPLC with CD Detection. Chirality 2005, 17(S1), S24–S29.
   PubMed Web of Science ®Google Scholar
• Lecoeur-Lorin, M.; Delépée, R.; Adamczyk, M.; Morin, P. Simultaneous Determination of Optical and Chemical Purities of a Drug with Two Chiral Centers by Liquid Chromatography-Circular Dichroism Detection on a Non-chiral Stationary Phase. J. Chrom. A 2008, 1206, 123–130.
   PubMed Web of Science ®Google Scholar
• Lecoeur-Lorin, M.; Delépée, R.; Ribet, J. P.; Morin, P. Chiral Analysis of Milnacipran by a Nonchiral HPLC – Circular Dichroism: Improvement of the Linearity of Dichroic Response by Temperature Control. J. Sep. Sci. 2008, 31, 3009–3014.
   PubMed Web of Science ®Google Scholar
• Lorin, M.; Delepee, R.; Maurizot, J. C.; Ribet, J. P.; Morin, P. Sensitivity Improvement of Circular Dichroism Detection in HPLC by Using a Low-pass Electronic Noise Filter: Application to the Enantiomeric Determination Purity of a Basic Drug. Chirality 2007, 19, 106–113.
   PubMed Web of Science ®Google Scholar
• Meyring, M.; Mühlbacher, J.; Messer, K.; Kastner-Pustet, N.; Bringmann, G.; Mannschreck, A.; Blaschke, G. In Vitro Biotransformation of (R)- and (S)-Thalidomide: Application of Circular Dichroism Spectroscopy to the Stereochemical Characterization of the Hydroxylated Metabolites. Anal. Chem. 2002, 74, 3726–3735.
   PubMed Web of Science ®Google Scholar
• Okuom, M. O.; Burks, R.; Naylor, C.; Holmes, A. E. Applied Circular Dichroism: A Facile Spectroscopic Tool for Configurational Assignment and Determination of Enantiopurity. J. Anal. Methods Chem. 2015, 2015, 6.
   Web of Science ®Google Scholar
• Sánchez, F. G.; Díaz, A. N.; de Vicente, A. B. M. Enantiomeric Resolution of Bupivacaine by High-performance Liquid Chromatography and Chiroptical Detection. J. Chromatogr. A 2008, 1188, 314–317.
   PubMed Web of Science ®Google Scholar
• Zougagh, M.; Aranda, P.; Castañeda, G.; Ríos, Á. Supercritical Fluid Extraction—Achiral Liquid Chromatography with Circular Dichroism Detection for the Determination of Menthone Enantiomers in Natural Peppermint Oil Samples. Talanta 2009, 79, 284–288.
   PubMed Web of Science ®Google Scholar
• Lieberman, P. Use of Epinephrine in the Treament of Anaphylaxis. Curr. Opin. Allergy Clin. Immunol. 2003, 3, 313–318.
   PubMedGoogle Scholar
• McLean-Tooke, A. P. C.; Bethune, C. A.; Fay, A. C.; Spickett, G. P. Adrenaline in the Treatment of Anaphylaxis: What is the Evidence? BMJ 2003, 327, 1332–1335.
   PubMed Web of Science ®Google Scholar
• Sampson, H. A. Anaphylaxis and Emergency Treatment. Pediatrics 2003, 111, 1601–1608.
   PubMed Web of Science ®Google Scholar
• Simons, F. E. R. Epinephrine (Adrenaline) in the First-Aid, Out-of-Hospital Treatment of Anaphylaxis. In G. Bock and J. Goode (Eds.) Anaphylaxis; John Wiley & Sons, Ltd, New York, 2008; 228–247 pp.
   Google Scholar
• Connors, K. A.; Amidon, G. L.; Stella, V. J. Chemical Stability of Pharmaceuticals: A Handbook for Pharmacists, 2nd ed. Wiley, New York, 1986, 864 p.
   Google Scholar
• Wilson, C. O.; Gisvold, O.; Delgado, J. N.; Remers, W. A. Wilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry. 10th ed.; Lippincott-Raven, Philadelphia, 1998.
   Google Scholar
• Simons, F. E. R.; Gu, X.; Simons, K. J. Outdated EpiPen and EpiPen Jr Autoinjectors: Past Their Prime? J. Allergy and Clin. Immunol. 2000, 105, 1025–1030.
   PubMed Web of Science ®Google Scholar
• Allgire, J. F.; Sullivan, G. M.; Kirchhoefer, R. D. Analysis of USP Epinephrine Injections for Potency, Impurities, Degradation Products, and D-Enantiomer by Liquid Chromatography, Using Ultraviolet and Electrochemical Detectors. J. Assoc. Off. Anal. Chem. 1985, 68, 163–165.
   PubMedGoogle Scholar
• Allgire, J. F.; Juenge, E. C.; Damo, C. P.; Sullivan, G. M.; Kirchhoefer, R. D. High-Performance Liquid Chromatographic Determination of D-/L-Epinephrine Enantiomer Ratio in Lidocaine-Epinephrine Local Anesthetics. J. Chromatog. A 1985, 325, 249–254.
   Web of Science ®Google Scholar
• Nimura, N.; Kasahara, Y.; Kinoshita, T. Resolution of Enantiomers of Norepinephrine and Epinephrine by Reversed-phase High-performance Liquid Chromatography. J. Chromatogr. A 1981, 213, 327–330.
   Web of Science ®Google Scholar
• Stepensky, D.; Chorny, M.; Dabour, Z.; Schumacher, I. Long-term Stability Study of L-Adrenaline Injections: Kinetics of Sulfonation and Racemization Pathways of Drug Degradation. J. Pharm. Sci. 2004, 93, 969–980.
   PubMed Web of Science ®Google Scholar
• Castro-Puyana, M.; Drewnowska, R.; Pérez-Fernández, V.; Ángeles García, M.; Crego, A. L.; Marina, M. L. Simultaneous Separation of Epinephrine and Norepinephrine Enantiomers by Ekc: Application to the Analysis of Pharmaceutical Formulations. Electrophor. 2009, 30, 2947–2954.
   PubMed Web of Science ®Google Scholar
• Epinephrine Injection. Pharmacopeia, U. S., Ed. Rockville, MD, USA, 2015; Vol. 39, 3713 p.
   Google Scholar
• Patil, P. N.; Fraundorfer, P.; Dutta, P. K. Stereoselective Modification of Circular Dichroism Spectra of Rat Lung B-Adrenoceptor Protein Preparation by Enantiomers of Epinephrine. Chirality 1996, 8, 463–465.
   PubMed Web of Science ®Google Scholar
• Miller, J. N.; Miller, J. C. Statistics and Chemometrics for Analytical Chemistry. Pearson/Prentice Hall, Harlow, Essex, England, 2010.
   Google Scholar
• Hoppe, J. O.; Seppelin, D. K.; Lands, A. M. An Investigation of the Acute Toxicity of the Optical Isomers of Arterenol and Epinephrine. J. Pharmacol. Exp. Ther. 1949, 95, 502–505.
   PubMed Web of Science ®Google Scholar