(–)-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).[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 |
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| Chlorine |
17 |
35.5 |
3.2 |
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| Bromine |
35 |
79.9 |
3.0 |
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| Iodine |
53 |
127 |
2.7 |
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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]
Data in Above table from rats brains (1995). More recent work has advocated using cloned human transporter/s.
[edit] See also
[edit] References
- ^ 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. edit
- ^ Stathis, M; Scheffel; Lever; Boja; Carroll; Kuhar (1995). "Rate of binding of various inhibitors at the dopamine transporter in vivo". Psychopharmacology 119 (4): 376–84. doi:10.1007/BF02245852. PMID 7480516. edit
- ^ 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. edit
- ^ 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. edit
- ^ Carroll, F. I.; Kotian, P.; Dehghani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H. et al (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. edit
- ^ Kozikowski, A. .; Johnson, K. .; Deschaux, O. .; Bandyopadhyay, B. .; Araldi, G. .; Carmona, G. .; Munzar, P. .; Smith, M. . et al (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. edit
- ^ Damaj, MI; Slemmer; Carroll; Martin (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. edit
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1-(4-Methylphenyl)-2-aminobutane • 1-Phenyl-2-(piperidin-1-yl)pentan-3-one • 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane • 2-Fluoroamphetamine • 2-Fluoromethamphetamine • 2-OH-PEA • 2-Phenyl-3-aminobutane • 2-Phenyl-3-methylaminobutane • 2,3-MDA • 3-Fluoroamphetamine • 3-Fluoroethamphetamine • 3-Fluoromethcathinone • 3-Methoxyamphetamine • 3-Methylamphetamine • 3,4-DMMC • 4-BMC • 4-Ethylamphetamine • 4-FA • 4-FMA • 4-MA • 4-MMA • 4-MTA • 6-FNE • Alfetamine • α-Ethylphenethylamine • Amfecloral • Amfepentorex • Amfepramone • Amidephrine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Arbutamine • β-Methylphenethylamine • β-Phenylmethamphetamine • Benfluorex • Benzedrone • Benzphetamine • BDB (J) • BOH (Hydroxy-J) • BPAP • Buphedrone • Bupropion (Amfebutamone) • Butylone • Cathine • Cathinone • Chlorphentermine • Cinnamedrine • Clenbuterol • Clobenzorex • Cloforex • Clortermine • D-Deprenyl • Denopamine • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Dobutamine • DOPA (Dextrodopa, Levodopa) • Dopamine • Dopexamine • Droxidopa • EBDB (Ethyl-J) • Ephedrine • Epinephrine (Adrenaline) • Epinine (Deoxyepinephrine) • Etafedrine • Ethcathinone (Ethylpropion) • Ethylamphetamine (Etilamfetamine) • Ethylnorepinephrine (Butanefrine) • Ethylone • Etilefrine • Famprofazone • Fenbutrazate • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenmetramide • Fenproporex • Flephedrone • Fludorex • Furfenorex • Gepefrine • HMMA • Hordenine • Ibopamine • IMP • Indanylamphetamine • Isoetarine • Isoethcathinone • Isoprenaline (Isoproterenol) • L-Deprenyl (Selegiline) • Lefetamine • Lisdexamfetamine • Lophophine (Homomyristicylamine) • Manifaxine • MBDB (Methyl-J; "Eden") • MDA (Tenamfetamine) • MDBU • MDEA ("Eve") • MDMA ("Ecstasy", "Adam") • MDMPEA (Homarylamine) • MDOH • MDPR • MDPEA (Homopiperonylamine) • Mefenorex • Mephedrone • Mephentermine • Metanephrine • Metaraminol • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methoxamine • Methoxyphenamine • MMA • Methcathinone (Methylpropion) • Methedrone • Methoxyphenamine • Methylone • MMDA • MMDMA • MMMA • Morazone • N-Benzyl-1-phenethylamine • N,N-Dimethylphenethylamine • Naphthylamphetamine • Nisoxetine • Norepinephrine (Noradrenaline) • Norfenefrine • Norfenfluramine • Normetanephrine • Octopamine • Orciprenaline • Ortetamine • Oxilofrine • Paredrine (Norpholedrine, Oxamphetamine, Mycadrine) • PBA • PCA • PHA • Pargyline • Pentorex (Phenpentermine) • Pentylone • Phenatine • Phendimetrazine • Phenmetrazine • Phenpromethamine • Phentermine • Phenylalanine • Phenylephrine (Neosynephrine) • Phenylpropanolamine • Pholedrine • PIA • PMA • PMEA • PMMA • PPAP • Prenylamine • Propylamphetamine • Pseudoephedrine • Radafaxine • Ropinirole • Salbutamol (Albuterol; Levosalbutamol) • Sibutramine • Synephrine (Oxedrine) • Theodrenaline • Tiflorex (Flutiorex) • Tranylcypromine • Tyramine • Tyrosine • Xamoterol • Xylopropamine • Zylofuramine
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- Adamantanes: Amantadine
- Memantine
- Rimantadine; Aminotetralins: 7-OH-DPAT
- 8-OH-PBZI
- Rotigotine
- UH-232; Benzazepines: 6-Br-APB
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- SKF-89,145
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- WAY-100,635
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- Morpholines: Fenbutrazate
- Morazone
- Phendimetrazine
- Phenmetrazine; Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX)
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- 4-CAB
- 4-Methylamphetamine (4-MA)
- 4-Methylmethamphetamine (4-MMA)
- Alfetamine
- Amfecloral
- Amfepentorex
- Amfepramone
- Amphetamine (Dextroamphetamine
- Levoamphetamine)
- Amphetaminil
- β-Methylphenethylamine (β-Me-PEA)
- Benzodioxolylbutanamine (BDB)
- Benzodioxolylhydroxybutanamine (BOH)
- Benzphetamine
- Buphedrone
- Butylone
- Cathine
- Cathinone
- Clobenzorex
- Clortermine
- D-Deprenyl
- Dimethoxyamphetamine (DMA)
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- Dimethylamphetamine
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- Ethcathinone (Ethylpropion)
- Ethylamphetamine
- Ethylbenzodioxolylbutanamine (EBDB)
- Ethylone
- Famprofazone
- Fenethylline
- Fenproporex
- Flephedrone
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- Furfenorex
- Hordenine
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- Mefenorex
- Mephedrone
- Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine
- Levomethamphetamine)
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- Methoxymethylenedioxymethamphetamine (MMDMA)
- Methylbenzodioxolylbutanamine (MBDB)
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- Methylenedioxyethylamphetamine (MDEA)
- Methylenedioxyhydroxyamphetamine (MDOH)
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- Methylenedioxymethylphenethylamine (MDMPEA, homarylamine)
- Methylenedioxyphenethylamine (MDPEA, homopiperonylamine)
- Methylone
- Ortetamine
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- Pholedrine
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- Tyramine (TRA)
- Xylopropamine
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- Benzylpiperazine (BZP)
- Methoxyphenylpiperazine (MeOPP, paraperazine)
- Methylbenzylpiperazine (MBZP)
- Methylenedioxybenzylpiperazine (MDBZP, piperonylpiperazine); Others: 2-Amino-1,2-dihydronaphthalene (2-ADN)
- 2-Aminoindane (2-AI)
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- 5-IAI
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- Naphthylaminopropane (NAP)
- Octodrine
- Phthalimidopropiophenone
- Propylhexedrine (Levopropylhexedrine)
- Tuaminoheptane (Tuamine)
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