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Chemical Compound Review

beta-CIT     methyl(1R,2S,3S,5S)-3-(4- iodophenyl)-8...

Synonyms: CHEMBL215376, SureCN221010, AG-D-68614, ANW-60213, CTK0I2863, ...
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Disease relevance of RTI 55


Psychiatry related information on RTI 55


High impact information on RTI 55


Chemical compound and disease context of RTI 55


Biological context of RTI 55

  • These studies demonstrate beta-CIT stereoselectivity using both homogenate binding and in vivo imaging and suggest that the inactive enantiomer may be a useful measure of the kinetics of both blood-brain barrier transport and nonspecific binding [14].
  • METHODS: We assessed genotype at the SLC6A3 promoter VNTR polymorphism in 96 healthy European Americans (age range, 18-88 y) who also underwent SPECT with (123)I-2beta-carbomethoxy-3beta-(4-iodophenyl)tropane (beta-CIT) for measurement of striatal DAT protein availability [15].
  • However, since [123I] beta-CIT binding is normal, a decreased number of D2-receptors or a decreased affinity of D2-receptors for [123I]IBZM is more likely than an increased level of synaptic DA with attendant downregulation of D2-receptors [16].
  • Saturation binding site analysis demonstrated an increase in the density of RTI-55 binding sites with no change in the affinity of the radioligand for the SERT [17].
  • We conclude that with no mutagenic effects and LD50 more than 6 orders of magnitude higher than the routinely used doses in PET or SPET, it can be assumed that beta-CIT can be safely used as a radioligand in humans [18].

Anatomical context of RTI 55

  • The relative reduction in [123I] beta-CIT uptake in the hemi-PD patients was greater in the putamen than in the caudate [19].
  • RESULTS: A significant negative correlation was found between a measure of overall tic severity and beta-CIT binding in the midbrain (r = -0.73, p = 0.02) and the thalamus (r = -0.82, p < 0.01) [20].
  • Cocaine and its analog RTI-55 [2 beta-carbomethoxy-3 beta-(4-iodophenyl-) tropane] inhibited the binding of haloperidol to placental membranes with appreciable potency [21].
  • This increase of [125I] beta-CIT binding does not come from de novo expression of DAT in glial cells in the damaged area in CPu [2].
  • Peak uptake of [123I] beta-CIT-FP into the basal ganglia occurred earlier (3-4 h after injection of tracer) than that of [123I] beta-CIT (> 8 h) [22].

Associations of RTI 55 with other chemical compounds

  • These data demonstrate that SPECT imaging of the dopamine transporter with [123I] beta-CIT can identify patients with PD at the onset of motor symptoms and suggest that this technique also may be useful in identifying individuals with developing dopaminergic pathology before onset of motor symptoms [19].
  • This report concerns the synthesis and chemical characterization of novel series of N-substituted 2 beta-carbomethoxy-3 beta-(4'-iodophenyl)tropane (beta-CIT, 2) analogs and their neuropharmacological evaluation for affinity at dopamine (DAT), serotonin (5-HTT), and norepinephrine membrane transporters in rat brain tissue [23].
  • 2beta-Carbomethoxy-3beta-(4-iodophenyl)nortropane (nor-beta-CIT) is a des-methyl analogue of beta-CIT, which in vitro has tenfold higher affinity (IC50=0.36 nM) to the serotonin transporter than beta-CIT (IC50=4.2 nM) [24].
  • To visualize possible alterations of the pre- and postsynaptic side of striatal dopaminergic synapses, SPECT studies using the radiotracers [123I] epidepride and [123I] beta-CIT were performed in 10 patients with idiopathic cervical dystonia [25].
  • Serotonin transporter density in cell membranes was monitored by measuring paroxetine-sensitive binding of RTI-55, a specific high-affinity ligand for the transporter [26].

Gene context of RTI 55

  • Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [(125)I] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells [27].
  • Synthesis and monoamine transporter affinity of 3'-analogs of 2-beta-carbomethoxy-3-beta-(4'-iodophenyl)tropane (beta-CIT) [28].
  • RTI-55 had similar affinity for the hDAT and hSERT and lower affinity for hNET (Kd = 1 [29].
  • Thus, we applied the high-resolution SPECT to in vivo imaging of the brain dopaminergic neurotransmission system in common marmosets using two radiolabeled ligands, [123I]2beta-carbomethoxy-3beta-(4-iodophenyl)tropane (beta-CIT) as a dopamine transporter (DAT) ligand and [123I]iodobenzamide (IBZM) as a dopamine D2 receptor (D2R) ligand [30].
  • RESULTS: The beta-CIT binding for the DAT was increased significantly in the caudate-putamen (CPu) of SH rats compared with that of Wistar-Kyoto (WKY) rats at both pre- and posthypertensive stages [31].

Analytical, diagnostic and therapeutic context of RTI 55

  • More recent studies have used surrogate markers of the integrity of nigrostriatal function such as striatal uptake of fluorodopa on positron emission tomography (PET) or beta-CIT-on single-photon emission computerized tomography (SPECT) as primary outcome measures [32].
  • At present, preparation of no-carrier-added (NCA) [123I] beta-CIT is achieved by iododestannylation of a trialkylstannyl precursor with sodium [123I]iodide in the presence of oxidizing agent, followed by preparative HPLC [33].
  • METHODS: The amounts of the dopamine transporter (DAT) and dopamine D1 and D2 receptors in the brain were assessed by in vitro autoradiography with the ligands [125I] beta-CIT, [125I]SCH23982 and [125I]iodospiperone, respectively [31].
  • A comparison of the ultrafiltration system with equilibrium dialysis revealed < 5% difference for beta-CIT and iomazenil, but 16% for IBF [34].
  • These data demonstrate that the dopaminergic nerve cell loss in PD and other disorders with a dopaminergic lesion can be quantified with [123I] beta-CIT and SPECT and that hopefully a preclinical or very early diagnosis is made possible [4].


  1. Topography of dopamine transporter availability in progressive supranuclear palsy: a voxelwise [123I]beta-CIT SPECT analysis. Seppi, K., Scherfler, C., Donnemiller, E., Virgolini, I., Schocke, M.F., Goebel, G., Mair, K.J., Boesch, S., Brenneis, C., Wenning, G.K., Poewe, W. Arch. Neurol. (2006) [Pubmed]
  2. Visualization of ischemic insult in caudate putamen with beta-CIT. Fujita, M., Shimada, S., Tohyama, M., Nishimura, T. J. Nucl. Med. (1996) [Pubmed]
  3. How useful is [123I]beta-CIT SPECT in clinical practice? Eerola, J., Tienari, P.J., Kaakkola, S., Nikkinen, P., Launes, J. J. Neurol. Neurosurg. Psychiatr. (2005) [Pubmed]
  4. Measurement of the dopaminergic degeneration in Parkinson's disease with [123I] beta-CIT and SPECT. Correlation with clinical findings and comparison with multiple system atrophy and progressive supranuclear palsy. Brücke, T., Asenbaum, S., Pirker, W., Djamshidian, S., Wenger, S., Wöber, C., Müller, C., Podreka, I. J. Neural Transm. Suppl. (1997) [Pubmed]
  5. N-(3-lodoprop-2E-enyl)-2beta-carbomethoxy-3beta-(3',4'-dichloro phenyl)nortropane (beta-CDIT), a tropane derivative: pharmacological characterization as a specific ligand for the dopamine transporter in the rodent brain. Garreau, L., Emond, P., Belzung, C., Guilloteau, D., Frangin, Y., Besnard, J.C., Chalon, S. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  6. Cloning, expression, and localization of a chloride-facilitated, cocaine-sensitive serotonin transporter from Drosophila melanogaster. Demchyshyn, L.L., Pristupa, Z.B., Sugamori, K.S., Barker, E.L., Blakely, R.D., Wolfgang, W.J., Forte, M.A., Niznik, H.B. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  7. Biophysical characterization of the cocaine binding pocket in the serotonin transporter using a fluorescent cocaine analogue as a molecular reporter. Rasmussen, S.G., Carroll, F.I., Maresch, M.J., Jensen, A.D., Tate, C.G., Gether, U. J. Biol. Chem. (2001) [Pubmed]
  8. Elevated striatal dopamine transporters during acute cocaine abstinence as measured by [123I] beta-CIT SPECT. Malison, R.T., Best, S.E., van Dyck, C.H., McCance, E.F., Wallace, E.A., Laruelle, M., Baldwin, R.M., Seibyl, J.P., Price, L.H., Kosten, T.R., Innis, R.B. The American journal of psychiatry. (1998) [Pubmed]
  9. In vivo association between alcohol intoxication, aggression, and serotonin transporter availability in nonhuman primates. Heinz, A., Higley, J.D., Gorey, J.G., Saunders, R.C., Jones, D.W., Hommer, D., Zajicek, K., Suomi, S.J., Lesch, K.P., Weinberger, D.R., Linnoila, M. The American journal of psychiatry. (1998) [Pubmed]
  10. Seasonal variation of availability of serotonin transporter binding sites in healthy female subjects as measured by [123I]-2 beta-carbomethoxy-3 beta-(4-iodophenyl)tropane and single photon emission computed tomography. Neumeister, A., Pirker, W., Willeit, M., Praschak-Rieder, N., Asenbaum, S., Brücke, T., Kasper, S. Biol. Psychiatry (2000) [Pubmed]
  11. SPECT imaging of the dopamine transporter with [(123)I]-beta-CIT reveals marked decline of nigrostriatal dopaminergic function in Parkinson's disease with urinary dysfunction. Sakakibara, R., Shinotoh, H., Uchiyama, T., Yoshiyama, M., Hattori, T., Yamanishi, T. J. Neurol. Sci. (2001) [Pubmed]
  12. Cocaine cross-sensitization to dopamine uptake inhibitors: unique effects of GBR12909. Elmer, G.I., Brockington, A., Gorelick, D.A., Carrol, F.I., Rice, K.C., Matecka, D., Goldberg, S.R., Rothman, R.B. Pharmacol. Biochem. Behav. (1996) [Pubmed]
  13. Receptor and transporter imaging studies in schizophrenia, depression, bulimia and Tourette's disorder--implications for psychopharmacology. Kasper, S., Tauscher, J., Willeit, M., Stamenkovic, M., Neumeister, A., Küfferle, B., Barnas, C., Stastny, J., Praschak-Rieder, N., Pezawas, L., de Zwaan, M., Quiner, S., Pirker, W., Asenbaum, S., Podreka, I., Brücke, T. World J. Biol. Psychiatry (2002) [Pubmed]
  14. Active and inactive enantiomers of 2 beta-carbomethoxy-3 beta-(4-iodophenyl)tropane: comparison using homogenate binding and single photon emission computed tomographic imaging. Scanley, B.E., Baldwin, R.M., Laruelle, M., al-Tikriti, M.S., Zea-Ponce, Y., Zoghbi, S., Giddings, S.S., Charney, D.S., Hoffer, P.B., Wang, S. Mol. Pharmacol. (1994) [Pubmed]
  15. Increased dopamine transporter availability associated with the 9-repeat allele of the SLC6A3 gene. van Dyck, C.H., Malison, R.T., Jacobsen, L.K., Seibyl, J.P., Staley, J.K., Laruelle, M., Baldwin, R.M., Innis, R.B., Gelernter, J. J. Nucl. Med. (2005) [Pubmed]
  16. SPECT imaging of striatal pre- and postsynaptic dopaminergic status in restless legs syndrome with periodic leg movements in sleep. Michaud, M., Soucy, J.P., Chabli, A., Lavigne, G., Montplaisir, J. J. Neurol. (2002) [Pubmed]
  17. Serotonin transporters upregulate with chronic cocaine use. Mash, D.C., Staley, J.K., Izenwasser, S., Basile, M., Ruttenber, A.J. J. Chem. Neuroanat. (2000) [Pubmed]
  18. Toxicity, mutagenicity, and behavioral effects of beta-CIT, a ligand for dopamine transporter exploration by SPECT. Emond, P., Farde, L., Chalon, S., Belzung, C., Mauclaire, V., Chiron, J.P., Halldin, C., Besnard, J.C., Guilloteau, D. Nucl. Med. Biol. (1998) [Pubmed]
  19. [123I] beta-CIT/SPECT imaging demonstrates bilateral loss of dopamine transporters in hemi-Parkinson's disease. Marek, K.L., Seibyl, J.P., Zoghbi, S.S., Zea-Ponce, Y., Baldwin, R.M., Fussell, B., Charney, D.S., van Dyck, C., Hoffer, P.B., Innis, R.P. Neurology (1996) [Pubmed]
  20. Tourette's syndrome: [I-123]beta-CIT SPECT correlates of vocal tic severity. Heinz, A., Knable, M.B., Wolf, S.S., Jones, D.W., Gorey, J.G., Hyde, T.M., Weinberger, D.R. Neurology (1998) [Pubmed]
  21. Cocaine-sensitive sigma-receptor and its interaction with steroid hormones in the human placental syncytiotrophoblast and in choriocarcinoma cells. Ramamoorthy, J.D., Ramamoorthy, S., Mahesh, V.B., Leibach, F.H., Ganapathy, V. Endocrinology (1995) [Pubmed]
  22. Comparison of iodine-123 labelled 2 beta-carbomethoxy-3 beta-(4-iodophenyl)tropane and 2 beta-carbomethoxy-3 beta-(4-iodophenyl)-N-(3-fluoropropyl)nortropane for imaging of the dopamine transporter in the living human brain. Kuikka, J.T., Bergström, K.A., Ahonen, A., Hiltunen, J., Haukka, J., Länsimies, E., Wang, S., Neumeyer, J.L. European journal of nuclear medicine. (1995) [Pubmed]
  23. N-substituted analogs of 2 beta-carbomethoxy-3 beta- (4'-iodophenyl)tropane (beta-CIT) with selective affinity to dopamine or serotonin transporters in rat forebrain. Neumeyer, J.L., Tamagnan, G., Wang, S., Gao, Y., Milius, R.A., Kula, N.S., Baldessarini, R.J. J. Med. Chem. (1996) [Pubmed]
  24. In vitro and in vivo characterisation of nor-beta-CIT: a potential radioligand for visualisation of the serotonin transporter in the brain. Bergström, K.A., Halldin, C., Hall, H., Lundkvist, C., Ginovart, N., Swahn, C.G., Farde, L. European journal of nuclear medicine. (1997) [Pubmed]
  25. Imaging the pre- and postsynaptic side of striatal dopaminergic synapses in idiopathic cervical dystonia: a SPECT study using [123I] epidepride and [123I] beta-CIT. Naumann, M., Pirker, W., Reiners, K., Lange, K.W., Becker, G., Brücke, T. Mov. Disord. (1998) [Pubmed]
  26. Cannabinoid receptors and their role in the regulation of the serotonin transporter in human placenta. Kenney, S.P., Kekuda, R., Prasad, P.D., Leibach, F.H., Devoe, L.D., Ganapathy, V. Am. J. Obstet. Gynecol. (1999) [Pubmed]
  27. Mazindol analogues as potential inhibitors of the cocaine binding site at the dopamine transporter. Houlihan, W.J., Kelly, L., Pankuch, J., Koletar, J., Brand, L., Janowsky, A., Kopajtic, T.A. J. Med. Chem. (2002) [Pubmed]
  28. Synthesis and monoamine transporter affinity of 3'-analogs of 2-beta-carbomethoxy-3-beta-(4'-iodophenyl)tropane (beta-CIT). Bois, F., Baldwin, R.M., Kula, N.S., Baldessarini, R.J., Innis, R.B., Tamagnan, G. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  29. Characteristics of drug interactions with recombinant biogenic amine transporters expressed in the same cell type. Eshleman, A.J., Carmolli, M., Cumbay, M., Martens, C.R., Neve, K.A., Janowsky, A. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  30. In vivo imaging of brain dopaminergic neurotransmission system in small animals with high-resolution single photon emission computed tomography. Saji, H., Iida, Y., Kawashima, H., Ogawa, M., Kitamura, Y., Mukai, T., Shimazu, S., Yoneda, F. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. (2003) [Pubmed]
  31. Brain dopamine transporter in spontaneously hypertensive rats. Watanabe, Y., Fujita, M., Ito, Y., Okada, T., Kusuoka, H., Nishimura, T. J. Nucl. Med. (1997) [Pubmed]
  32. Neuroprotection in Parkinson's disease: clinical trials. Stocchi, F., Olanow, C.W. Ann. Neurol. (2003) [Pubmed]
  33. Simplified multidose preparation of iodine-123-beta-CIT: a marker for dopamine transporters. Zea-Ponce, Y., Baldwin, R.M., Laruelle, M., Wang, S., Neumeyer, J.L., Innis, R.B. J. Nucl. Med. (1995) [Pubmed]
  34. Evaluation of ultrafiltration for the free-fraction determination of single photon emission computed tomography (SPECT) radiotracers: beta-CIT, IBF, and iomazenil. Gandelman, M.S., Baldwin, R.M., Zoghbi, S.S., Zea-Ponce, Y., Innis, R.B. Journal of pharmaceutical sciences. (1994) [Pubmed]
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