|Systematic (IUPAC) name|
|Mol. mass||338.240 g/mol|
(–)-2β-Carbomethoxy-3β-(4-bromophenyl)tropane (RTI-51, bromopane) is a semi-synthetic alkaloid in the phenyltropane group of psychostimulant compounds. First publicized in the 1990s, it has not been used enough to have gained a fully established profile. RTI-51 can be expected to have properties lying somewhere in between RTI-31 and RTI-55. Importantly it has a ratio of monoamine reuptake inhibition of D > S > N (1.8:10.6:37.4nM respectively) which is an unusual balance of effects not produced by other commonly used compounds (although RTI-121 is similar, but more DAT selective). It has been used in its 76Br radiolabelled form to map the distribution of dopamine transporters in the brain.
|Halogen||Atomic №||Atomic Weight||EN||Bond Length|
Modern research seems to confirm the above hypothesis. However, earlier work produced more scattered results. Based upon what is obvious from the table, RTI-31, RTI-51, and RTI-55 are all similarly potent TRIs.
|MAT IC50 (and Ki) for simple phenyltropanes with 1R,2S,3S stereochemistry.|
|Cocaine||89.1||275 cf. 241||3300 (1990)||119 cf. 161||1050 (45)||177 cf. 112|
|WIN 35,065-2||23||49.8||920 (550)||37.2||1960 (178)||173|
|WIN 35,428||13.9||23.0||835 (503)||38.6||692 (63)||101|
|RTI-31||1.1||3.68||37 (22)||5.86||44.5 (4.0)||5.00|
|RTI-51||1.7||?||37.4 (23)||?||10.6 (0.96)||?|
|RTI-55||1.3||1.96||36 (22)||7.51||4.21 (0.38)||1.74|
|RTI-32||1.7||7.02||60 (36)||8.42||240 (23)||19.4|
Data in Above table from rats brains (1995). More recent work has advocated using cloned human transporter/s.
- Singh S (March 2000). "Chemistry, design, and structure-activity relationship of cocaine antagonists". Chemical Reviews 100 (3): 925–1024.
- Loch C, Müller L, Ottaviani M, Halldin C, Farde L, Maziere B. Synthesis of 2β-carbomethoxy-3β-(4-[76Br]bromophenyl)tropane ([76Br]β-CBT), a PET tracer for in vivo imaging of the dopamine uptake sites. Journal of labelled compounds & radiopharmaceuticals. 1995; 36(4):385-392.
- Wee, S.; Carroll, F.; Woolverton, W. (2006). "A reduced rate of in vivo dopamine transporter binding is associated with lower relative reinforcing efficacy of stimulants". Neuropsychopharmacology 31 (2): 351–362.
- Stathis, M.; Scheffel, U.; Lever, S. Z.; Boja, J. W.; Carroll, M. J.; Kuhar, F. I. (1995). "Rate of binding of various inhibitors at the dopamine transporter in vivo". Psychopharmacology 119 (4): 376–384.
- Kimmel, HL; Carroll; Kuhar (2001). "Locomotor stimulant effects of novel phenyltropanes in the mouse". Drug and alcohol dependence 65 (1): 25–36.
- Kuhar, M.; Carroll, F.; Bharat, N.; Landry, D. (2001). "Anticocaine catalytic antibodies have no affinity for RTI compounds: implications for treatment". Synapse 41 (2): 176–178.
- Carroll, F. I.; Kotian, P.; Dehghani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. (1995). "Cocaine and 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter". Journal of Medical Chemistry 38 (2): 379–388.
- Kozikowski, A.; Johnson, K.; Deschaux, O.; Bandyopadhyay, B.; Araldi, G.; Carmona, G.; Munzar, P.; Smith, M.; Balster, R. (2003). "Mixed cocaine agonist/antagonist properties of (+)-methyl 4beta-(4-chlorophenyl)-1-methylpiperidine-3alpha-carboxylate, a piperidine-based analog of cocaine". The Journal of Pharmacology and Experimental Therapeutics 305 (1): 143–150.
- Damaj, M. I.; Slemmer, J. E.; Carroll, F. I.; Martin, B. R. (1999). "Pharmacological characterization of nicotine's interaction with cocaine and cocaine analogs". The Journal of Pharmacology and Experimental Therapeutics 289 (3): 1229–1236.