Synthesis of 11C-labeled desipramine and its metabolite 2- hydroxydesipramine: Potential radiotracers for PET studies of the norepinephrine transporter

Nuclear Medicine and Biology

Volumn 24, Issue 8, 1997, Pages 707-711

  Van Dort, Marcian E ^a   Kim, Jae Hoon ^a,b   Tluczek, Louis ^a   Wieland, Donald M ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^b Kumoh National Institute of Technology   (South Korea)

Author keywords

2 Hydroxydesipramine; Antidepressant; Carbon 11; Desipramine; Norepinephrine transporter; Positron emission tomography; Radiotracer

Indexed keywords

2 HYDROXYDESIPRAMINE; ANTIDEPRESSANT AGENT; CARBON 11; DESIPRAMINE; NORADRENALIN; TRACER; 2-HYDROXYDESIPRAMINE; CARBON; CARRIER PROTEIN; COTRANSPORTER; DRUG DERIVATIVE; NORADRENALIN TRANSPORTER; RADIOPHARMACEUTICAL AGENT;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; METHYLATION; NORADRENALIN RELEASE; POSITRON EMISSION TOMOGRAPHY; CHEMISTRY; COMPUTER ASSISTED EMISSION TOMOGRAPHY; METHODOLOGY; SYNTHESIS;

CARBON RADIOISOTOPES; CARRIER PROTEINS; DESIPRAMINE; ISOTOPE LABELING; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; RADIOPHARMACEUTICALS; SYMPORTERS; TOMOGRAPHY, EMISSION-COMPUTED;

EID: 0030608673     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(97)00109-1     Document Type: Article

References (14)

1. Adamczyk M., Chen Y.-Y. and Fishpaugh J. R. (1991) A facile synthetic route to hydroxy metabolites of tricyclic antidepressants. Org. Prep. Proc. Int. 23, 365-372.
2. Bohm M., La Rosee K., Schwinger R. H. G. and Erdmann E. (1995) Evidence for reduction of norepinephrine uptake sites in the failing human heart. J. Am. Coll. Cardiol. 25, 146-153.
3. Bonisch H. and Bruss M. (1994) The noradrenaline transporter of the neuronal plasma membrane. Ann. N. Y. Acad. Sci. 733, 193-202.
4. 11C]methyl iodide. Appl. Radiat. Isot. 38, 601-603.
5. 11C]methyl)-imipramine. J. Nucl. Med. 24, 1185-1187.
6. Fuller R. W. (1981) Enhancement of monoaminergic transmission by antidcprcssant drugs. In Antidepressants: Neurochemical, Behavioral, and Clinical Perspectives (Edited by Enna S. J., Mallick J. B. and Richelson E.), pp. 1-13. Raven Press, New York.
7. Geigy J. R. (1963) 5-Substituted 5H-dibenz[b,f]azepines and their 10,11-dihydro derivatives. Chem. Abstr. 59, 10011a.
8. Javaid J. I., Perel J. M. and Davis J. M. (1979) Inhibition of biogenic amines uptake by imipramine, desipramine, 2-OH-imipramine and 2-OH-desipramine in rat brain. Life Sci. 24, 21-28.
9. Purchase C. F. II and Goel O. P. (1991) A new synthesis of primary aliphatic amines by N,N-didebenzylation: Synthesis of a pirmenol (Cl-845) metabolite J. Org. Chem. 56, 457-459.
10. 3H]desiprainine binding in the peripheral and central nervous system: A specific site associated with the neuronal uptake of noradrenaline. Eur. J. Pharmacol. 78, 345-351.
11. Stern S. L., Cooper T. B., Nelson L. D., Johnson M. H. and Suckow R. F. (1996) 2-Hydroxydesipramine and desipramine plasma levels: How are they related to antidepressant response? Int. Clin. Psychopharmacol. 11, 219-227.
12. Still W. C., Kahn M. and Mitra A. (1978) Rapid Chromatographic technique for preparative separations with moderate resolution. J. Org. Chem. 43, 2923-2925.
13. Trendelenberg U. (1991) The TIPS lecture: Functional aspects of the neuronal uptake of noradrenaline. Trends Pharmacol. Sci. 12, 334-337.
14. Ungerer M., Chlistalla A. and Richardt G. (1996) Upregulation of cardiac uptake 1 carrier in ischemic and nonischemic rat heart. Circ. Res. 78, 1037-1043.