RTI-51
Chemical compound
title: "RTI-51" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["4-bromophenyl-compounds", "tropanes", "rti-compounds", "dopamine-reuptake-inhibitors", "sympathomimetic-amines", "medical-imaging", "neuroimaging", "methyl-esters"] description: "Chemical compound" topic_path: "general/4-bromophenyl-compounds" source: "https://en.wikipedia.org/wiki/RTI-51" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Chemical compound ::
::data[format=table title="Infobox drug"]
| Field | Value |
|---|---|
| Verifiedfields | changed |
| Watchedfields | changed |
| verifiedrevid | 449586292 |
| IUPAC_name | methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate |
| image | RTI-51.png |
| image_class | skin-invert-image |
| CAS_number_Ref | |
| CAS_number | 135367-08-7 |
| UNII_Ref | |
| UNII | C3MV2GV7R7 |
| PubChem | 22595194 |
| C | 16 |
| smiles | Brc1ccc(cc1)[C@H]2C[C@@H]3N(C)C@HCC3 |
| StdInChI_Ref | |
| StdInChI | 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 |
| StdInChIKey_Ref | |
| StdInChIKey | HNVGNUVAMRLMSG-KBXIAJHMSA-N |
| :: |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449586292 | IUPAC_name = methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | image = RTI-51.png | image_class = skin-invert-image
| tradename =
| CAS_number_Ref = | CAS_number = 135367-08-7 | UNII_Ref = | UNII = C3MV2GV7R7 | ATC_prefix = | ATC_suffix = | PubChem = 22595194
| C=16 | H=20 | Br=1 | N=1 | O=2 | smiles = Brc1ccc(cc1)[C@H]2C[C@@H]3N(C)C@HCC3 | StdInChI_Ref = | StdInChI=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 | StdInChIKey_Ref = | StdInChIKey = HNVGNUVAMRLMSG-KBXIAJHMSA-N
(–)-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). It has been used in its radiolabelled form to map the distribution of dopamine transporters in the brain.
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.
::data[format=table title="[[Monoamine transporter|MAT]] [[IC50|IC50]] (and [[Dissociation constant|Ki]]) for simple [[phenyltropanes]] with 1R,2S,3S [[stereochemistry]].{{cite journal | vauthors = Carroll FI, Kotian P, Dehghani A, Gray JL, Kuzemko MA, Parham KA, Abraham P, Lewin AH, Boja JW, Kuhar MJ | display-authors = 6 | title = 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 = Journal of Medicinal Chemistry | volume = 38 | issue = 2 | pages = 379–88 | date = January 1995 | pmid = 7830281 | doi = 10.1021/jm00002a020 }}"]
| Compound | [3H]CFT | [3H]DA | [3H]Nisoxetine | [3H]NE | [3H]Paroxetine | [3H]5-HT |
|---|---|---|---|---|---|---|
| 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-113 | 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.
References
References
- (March 2000). "Chemistry, design, and structure-activity relationship of cocaine antagonists". Chemical Reviews.
- 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.
- (February 2006). "A reduced rate of in vivo dopamine transporter binding is associated with lower relative reinforcing efficacy of stimulants". Neuropsychopharmacology.
- (June 1995). "Rate of binding of various inhibitors at the dopamine transporter in vivo". Psychopharmacology.
- (December 2001). "Locomotor stimulant effects of novel phenyltropanes in the mouse". Drug and Alcohol Dependence.
- (August 2001). "Anticocaine catalytic antibodies have no affinity for RTI compounds: implications for treatment". Synapse.
- (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.
- (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.
- (June 1999). "Pharmacological characterization of nicotine's interaction with cocaine and cocaine analogs". The Journal of Pharmacology and Experimental Therapeutics.
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