NMR Studies of Drugs. Applications of Achiral and Chiral Lanthanide Shift Reagents to Medetomidine. Observations of “Anomalous Shifts.”

References

• Virtanen , R. , Viitamaa , T. and Nyman , L. 1988 . Pharmacological properties of the enantiomers of the α2-agonist medetomidine . Psychopharmacology Suppl , 96 : 371 abstr. no. 34.01.28. Abstracts of the XVI th C.I.N.P. Congress, Munich, Aug. 1988 (Collegium Internationale Neuro-Psychopharmacologicum).
   Google Scholar
• Turpeinen , U. , Ruotsalainen , H. , Pehkonen , R. , Lajunen , L. H. J. and Karjalainen , A. 1988 . Crystal structure, thermal behaviour, protonation and mass spectroscopic studies of racemic 4-[1-(2,3-dimethylphenyl) ethyl]-1H-imidazole hydrochlorides . Acta Chem. Scand. , B42 : 537 – 545 .
   Google Scholar
• Virtanen , R. 1989 . Pharmacological profiles of medetomidine and its antagonist, atipamezole . Acta Vet. Scand. , 85 : 29 – 37 .
   Google Scholar
• Aantaa , R. , Kanto , J. , Scheinin , M. , Kallio , A. and Scheinin , H. 1990 . 73 ( 2 ) : 230 – 235 . Dexmedetomidine, an α2-adrenoceptor agonist, reduces anesthetic requirements for patients undergoing minor gynecologic surgery. Anesthesiology
   Google Scholar
• Savola , J.-M. and Virtanen , R. 1991 . Central α2-adrenoceptors are highly stereoselective for dexmedetomidine, the dextro enantiomer of medetomidine. Eur. . J. Pharmacol. , 195 : 193 – 199 .
   Google Scholar
• Aho , M. , Lehtinen , A.-M , Erkola , O. , Kallio , A. and Korttila , K. 1991 . The effect of intravenously administered dexmedetomidine on perioperative hemodynamics and isoflurane requirements in patients undergoing abdominal hysterectomy. Anesthesiology . 74 ( 6 ) : 997 – 1002 .
   Google Scholar
• Örn , G. , Lahtonen , K. and Jalonen , H. 1990 . Direct high-performance liquid chromatographic separation of (+)-and (-)-medetomidine hydrochloride with an α1-acid glycoprotein chiral column . J. Chromatogr. , 506 : 627 – 635 .
   Google Scholar
• Kivikoski , J. H. , Rissanen , K. T. and Parhi , S. S. L. 1993 . Crystal structures and absolute configurations of dexmedetomidine and its tosyl derivative. Tetrahedron: Asymmetry . 4 ( 1 ) : 45 – 58 .
   Google Scholar
• Cockerill , A. F. , Davies , G. L. O. , Harden , R. C. and Rackham , D. M. 1973 . Lanthanide shift reagents for nuclear magnetic resonance spectroscopy . Chem. Rev. , 73 ( 6 ) : 553 – 588 .
   Web of Science ®Google Scholar
• Aboul-Enein , H. Y. 1988 . NMR methods for optical purity determination of pharmaceuticals. . Anal. Lett. , 21 ( 12 ) : 2155 – 2163 .
   Web of Science ®Google Scholar
• Morrill , T. C. , ed. 1986 . Lanthanide Shift Reagents in Stereochemical Analysis , New York : VCH .
   Google Scholar
• Wenzel , T. J. 1987 . NMR Shift Reagents , Boca Raton, FL : CRC Press .
   Google Scholar
• Abraham , R. J. , Fisher , J. and Loftus , P. 1988 . Introduction to NMR Spectroscopy , 31 Chichester, New York : John Wiley .
   Google Scholar
• Abraham , R. J. , Fisher , J. and Loftus , P. 1988 . Introduction to NMR Spectroscopy , 23 – 24 . Chichester, New York : John Wiley .
   Google Scholar
• Wenzel , T. J. 1987 . NMR Shift Reagents , 6–7, 25, 171–172 Boca Raton, FL : CRC Press . esp. and references cited therein.
   Google Scholar
• McConnell , H. M. and Robertson , R. E. 1958 . Isotropic nuclear resonance shifts. . J. Chem. Phys. , 29 ( 6 ) : 1361 – 1365 .
   Web of Science ®Google Scholar
• Reilley , C. N. , Good , B. W. and Allendoerfer , R. D. 1976 . Separation of contact and dipolar lanthanide induced nuclear magnetic resonance shifts: evaluation and application of some structure independent methods . Anal. Chem , 48 ( 11 ) : 1446 – 1458 . and references cited therein.
   Web of Science ®Google Scholar
• LaPlanche , L. A. , Rothchild , R. and Xu , Y. 1992 . 1H and 13C NMR studies of etidocaine free base and hydrochloride salt. Solvent and temperature dependence. Spectrosc. Lett . 25 ( 1 ) : 133 – 161 .
   Google Scholar
• Ross , J. and Rothchild , R. 1989 . 1H NMR spectral simplification with achiral and chiral lanthanide shift reagents Lofexidine. Spectrosc. Lett. . 22 ( 7 ) : 869 – 891 .
   Google Scholar
• Peters , J. A. , Nieuwenhuizen , M. S. and Raber , D. J. 1985 . Analysis of multinuclear lanthanide-induced shifts. 1. Investigations of some approximations in the procedure for separation of diamagnetic, contact and pseudocontact shifts . J. Magn. Reson. , 65 : 417 – 428 .
   Web of Science ®Google Scholar