RTI-51

RTI-51
Systematic (IUPAC) name
	methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Identifiers
CAS Number	135367-08-7
PubChem	CID 22595194
Chemical data
Formula	C16H20BrNO2
Molar mass	338.240 g/mol
	SMILES Brc1ccc(cc1)[C@H]2C[C@@H]3N(C)[C@H]([C@H]2C(=O)OC)CC3 ;
	InChI InChI=1S/C16H20BrNO2/c1-18-12-7-8-14(18)15(16(19)20-2)13(9-12)10-3-5-11(17)6-4-10/h3-6,12-15H,7-9H2,1-2H3/t12-,13-,14+,15+/m1/s1 ; Key:HNVGNUVAMRLMSG-KBXIAJHMSA-N ;
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(–)-2β-Carbomethoxy-3β-(4-bromophenyl)tropane (RTI-4229-51, 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).^[1] It has been used in its ⁷⁶Br radiolabelled form to map the distribution of dopamine transporters in the brain.^[2]

Comparison of halogens
Halogen	Atomic №	Atomic Weight	EN	Bond Length
Fluorine	9	19.0	4.0
Chlorine	17	35.5	3.2
Bromine	35	79.9	3.0
Iodine	53	127	2.7

Modern research seems to confirm the above hypothesis.^[3] However, earlier work produced more scattered results.^[4] Based upon what is obvious from the table, RTI-31, RTI-51, and RTI-55 are all similarly potent TRIs.^[5]^[6]

MAT IC₅₀ (and K_i) for simple phenyltropanes with 1R,2S,3S stereochemistry.^[7]
Compound	[³H]CFT	[³H]DA	[³H]Nisoxetine	[³H]NE	[³H]Paroxetine	[³H]5-HT
Cocaine^[8]	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-113^[9]	1.98	5.25	2,926	242	2,340	391
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.

References[edit]

^ Singh S (March 2000). "Chemistry, design, and structure-activity relationship of cocaine antagonists". Chemical Reviews 100 (3): 925–1024. doi:10.1021/cr9700538. PMID 11749256.
^ 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. doi:10.1038/sj.npp.1300795. PMID 15957006.
^ 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. doi:10.1007/BF02245852. PMID 7480516.
^ Kimmel, HL; Carroll; Kuhar (2001). "Locomotor stimulant effects of novel phenyltropanes in the mouse". Drug and Alcohol Dependence 65 (1): 25–36. doi:10.1016/S0376-8716(01)00144-2. PMID 11714587.
^ 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. doi:10.1002/syn.1072. PMID 11400184.
^ 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 Medicinal Chemistry 38 (2): 379–388. doi:10.1021/jm00002a020. PMID 7830281.
^ 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. doi:10.1124/jpet.102.046318. PMID 12649362.
^ 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. PMID 10336510.

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[pmid11749256-1] Singh S (March 2000). "Chemistry, design, and structure-activity relationship of cocaine antagonists". Chemical Reviews 100 (3): 925–1024. doi:10.1021/cr9700538. PMID 11749256.

[2] 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.

[3] 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. doi:10.1038/sj.npp.1300795. PMID 15957006.

[4] 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. doi:10.1007/BF02245852. PMID 7480516.

[5] Kimmel, HL; Carroll; Kuhar (2001). "Locomotor stimulant effects of novel phenyltropanes in the mouse". Drug and Alcohol Dependence 65 (1): 25–36. doi:10.1016/S0376-8716(01)00144-2. PMID 11714587.

[6] 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. doi:10.1002/syn.1072. PMID 11400184.

[7] 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 Medicinal Chemistry 38 (2): 379–388. doi:10.1021/jm00002a020. PMID 7830281.

[8] 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. doi:10.1124/jpet.102.046318. PMID 12649362.

[9] 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. PMID 10336510.

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RTI-51

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