(–)-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. It has a ratio of monoamine reuptake inhibition of dopamine > serotonin > norepinephrine (1.8:10.6:37.4 nM 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 76Brradiolabelled form to map the distribution of dopamine transporters in the brain.[2]
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]
^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 FI, Woolverton WL (February 2006). "A reduced rate of in vivo dopamine transporter binding is associated with lower relative reinforcing efficacy of stimulants". Neuropsychopharmacology. 31 (2): 351–62. doi:10.1038/sj.npp.1300795. PMID 15957006. S2CID 7224342.
^Stathis M, Scheffel U, Lever SZ, Boja JW, Carroll FI, Kuhar MJ (June 1995). "Rate of binding of various inhibitors at the dopamine transporter in vivo". Psychopharmacology. 119 (4): 376–84. doi:10.1007/BF02245852. PMID 7480516. S2CID 20022021.
^Kimmel HL, Carroll FI, Kuhar MJ (December 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 MJ, Carroll FI, Bharat N, Landry DW (August 2001). "Anticocaine catalytic antibodies have no affinity for RTI compounds: implications for treatment". Synapse. 41 (2): 176–8. doi:10.1002/syn.1072. PMID 11400184. S2CID 11862673.
^Carroll FI, Kotian P, Dehghani A, Gray JL, Kuzemko MA, Parham KA, et al. (January 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): 379–88. doi:10.1021/jm00002a020. PMID 7830281.
^Kozikowski AP, Johnson KM, Deschaux O, Bandyopadhyay BC, Araldi GL, Carmona G, et al. (April 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): 143–50. doi:10.1124/jpet.102.046318. PMID 12649362. S2CID 29377097.
^Damaj MI, Slemmer JE, Carroll FI, Martin BR (June 1999). "Pharmacological characterization of nicotine's interaction with cocaine and cocaine analogs". The Journal of Pharmacology and Experimental Therapeutics. 289 (3): 1229–36. PMID 10336510.
January 01, 1970
carbomethoxy, bromophenyl, tropane, 4229, bromopane, semi, synthetic, alkaloid, phenyltropane, group, psychostimulant, compounds, first, publicized, 1990s, been, used, enough, have, gained, fully, established, profile, expected, have, properties, lying, somewh. 2b Carbomethoxy 3b 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 It has a ratio of monoamine reuptake inhibition of dopamine gt serotonin gt norepinephrine 1 8 10 6 37 4 nM 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 RTI 51IdentifiersIUPAC name methyl 1R 2S 3S 5S 3 4 bromophenyl 8 methyl 8 azabicyclo 3 2 1 octane 2 carboxylateCAS Number135367 08 7 YPubChem CID22595194CompTox Dashboard EPA DTXSID40720932Chemical and physical dataFormulaC 16H 20Br N O 2Molar mass338 245 g mol 13D model JSmol Interactive imageSMILES Brc1ccc cc1 C H 2C C H 3N C C H C H 2C O OC CC3InChI 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 NKey HNVGNUVAMRLMSG KBXIAJHMSA N N N Y what is this verify 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 Ki 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 is from rats brains 1995 More recent work has advocated using cloned human transporters See also editList of cocaine analoguesReferences 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 Muller L Ottaviani M Halldin C Farde L Maziere B Synthesis of 2b carbomethoxy 3b 4 76Br bromophenyl tropane 76Br b CBT a PET tracer for in vivo imaging of the dopamine uptake sites Journal of labelled compounds amp radiopharmaceuticals 1995 36 4 385 392 Wee S Carroll FI Woolverton WL February 2006 A reduced rate of in vivo dopamine transporter binding is associated with lower relative reinforcing efficacy of stimulants Neuropsychopharmacology 31 2 351 62 doi 10 1038 sj npp 1300795 PMID 15957006 S2CID 7224342 Stathis M Scheffel U Lever SZ Boja JW Carroll FI Kuhar MJ June 1995 Rate of binding of various inhibitors at the dopamine transporter in vivo Psychopharmacology 119 4 376 84 doi 10 1007 BF02245852 PMID 7480516 S2CID 20022021 Kimmel HL Carroll FI Kuhar MJ December 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 MJ Carroll FI Bharat N Landry DW August 2001 Anticocaine catalytic antibodies have no affinity for RTI compounds implications for treatment Synapse 41 2 176 8 doi 10 1002 syn 1072 PMID 11400184 S2CID 11862673 Carroll FI Kotian P Dehghani A Gray JL Kuzemko MA Parham KA et al January 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 88 doi 10 1021 jm00002a020 PMID 7830281 Kozikowski AP Johnson KM Deschaux O Bandyopadhyay BC Araldi GL Carmona G et al April 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 50 doi 10 1124 jpet 102 046318 PMID 12649362 S2CID 29377097 Damaj MI Slemmer JE Carroll FI Martin BR June 1999 Pharmacological characterization of nicotine s interaction with cocaine and cocaine analogs The Journal of Pharmacology and Experimental Therapeutics 289 3 1229 36 PMID 10336510 Retrieved from https en wikipedia org w index php title RTI 51 amp oldid 1187399265, wikipedia, wiki, book, books, library,
