Practical Synthesis of p‐Aminophenethylspiperone (NAPS), a High‐Affinity, Selective D₂‐Dopamine Receptor Antagonist

References

• Amlaiky , N. and Caron , M. G. 1985 . Photoaffinity labeling of the D2‐dopamine receptor using a novel high affinity radioiodinated probe . J. Biol. Chem. , 260 : 1983 – 1986 .
   PubMed Web of Science ®Google Scholar
• Amlaiky , N. , Kilpatrick , B. F. and Caron , M. G. 1984 . A novel radioiodinated high affinity ligand for D2‐dopamine receptor . FEBS , 176 : 436 – 440 .
   PubMed Web of Science ®Google Scholar
• Agui , T. , Amlaiky , N. , Caron , M. G. and Kebabian , J. W. 1988 . Binding of [125I]‐N‐(p‐aminophenethyl)spiroperidol to the D‐2 dopamine receptor in the neurointermediate lobe of the rat pituitary gland: a thermodynamic study . Mol. Pharmacol. , 32 : 163 – 169 .
   Google Scholar
• Ariano , M. A. , Monsma , F. J. Jr. , Barton , A. C. , Kang , H. C. , Haugland , R. P. and Sibley , D. R. 1989 . Direct visualization and cellular localization of D1 and D2 dopamine receptors in rat forebrain by use of fluorescent ligands . Proc. Natl. Acad. Sci. USA , 86 : 8570 – 8574 .
   PubMed Web of Science ®Google Scholar
• Monsma , F. J. Jr. , Barton , A. C. , Kang , H. C. , Brassard , D. L. , Haugland , R. P. and Sibley , D. R. 1989 . Characterization of novel fluorescent ligands with high affinity for D1 and D2 dopaminergic receptors . J. Neurochem. , 52 : 1641 – 1644 .
   PubMed Web of Science ®Google Scholar
• Madras , B. K. , Canfield , D. R. , Praelzer , C. , Vittimberga , F. J. Jr. , Difiglia , M. , Aronin , N. , Bakthavachalam , V. , Baindur , N. and Neumeyer , J. L. 1990 . Fluorescent and biotin probes for dopamine receptors: D1 and D2 receptor affinity and selectivity . Mol. Pharmocol. , 37 : 833 – 839 .
   PubMed Web of Science ®Google Scholar
• Rayport , S. and Sulzer , D. 1995 . Visualization of antipsychotic drug binding to living mesolimbic neurons reveals D2 receptor, acidotropic, and lipophilic components . J. Neurochem. , 65 : 691 – 703 .
   PubMed Web of Science ®Google Scholar
• Amlaiky , N. and Caron , M. G. 1986 . Identification of the D2‐dopamine receptor binding subunit in several mammalian tissues and species by photoaffinity labeling . J. Neurochem. , 47 : 196 – 204 .
   PubMed Web of Science ®Google Scholar
• Bakthavachalam , V. , Baindur , N. , Madras , B. K. and Neumeyer , J. L. 1991 . Fluorescent probes for dopamine receptors: synthesis and characterization of fluorescein and 7‐nitrobenz‐2‐oxa‐1,3‐diazol‐4‐yl conjugates of D‐1 and D‐2 receptor ligands . J. Med. Chem. , 34 : 3235 – 3241 .
   PubMed Web of Science ®Google Scholar
• Mach , R. H. , Jackson , J. R. , Leudtke , R. R. , Ivins , K. J. , Molinoff , P. B. and Ehrenkaufer , R. L. 1992 . Effect of N‐alkylation on the affinities of analogues of spiperone for dopamine D2 and serotonin 5‐HT2 receptors . J. Med. Chem. , 35 : 423 – 430 .
   PubMed Web of Science ®Google Scholar
• Hass , H. B. and Bender , M. L. 1949 . A proposed mechanism of the alkylation of benzyl halides with nitro paraffin salts . J. Am. Chem. Soc. , 71 : 3482 – 3485 .
   Web of Science ®Google Scholar
• Saunders , W. H. Jr. and Williams , R. A. 1956 . Mechanisms of elimination reactions, II: rates of elimination from some substituted 2‐phenylethyl bromides and 2‐phenylethyldimethylsulfonium bromides . J. Am. Chem. Soc. , 79 : 3712 – 3716 .
   Web of Science ®Google Scholar
• Alumni , S. and Jencks , W. P. 1980 . Catalysis of the reversible elimination reaction of substituted N‐(β‐phenylethyl)quinuclidinium ions in aqueous solution . J. Am. Chem. Soc. , 102 : 2052 – 2060 .
   Web of Science ®Google Scholar
• Saulnier , M. G. , Zimmermann , K. , Struzynski , C. P. , Sang , X. P. , Velaparthi , U. , Wittman , M. and Frennesson , D. B. 2004 . Tetrahedron Lett. , 45 : 397 – 399 .
   Web of Science ®Google Scholar
• Wilcox , C. S. 1985 . New structural units for the preparation of chiral hosts and metal ligands . Tetrahedron Lett. , 26 : 5749 – 6762 .
   Web of Science ®Google Scholar
• Azibi , M. , Draguet‐Brughmans , M. , Bouche , R. , Tinant , B. , Germain , G. , Declercq , J. P. and van Meerssche , M. 2006 . Conformational study of two polymorphs of spiperone: possible consequences on the interpretation of pharmacological activity . J. Pharm. Sci. , 72 : 232 – 235 .
   Web of Science ®Google Scholar