RTI-51

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RTI-51
RTI-51.png
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 YesY
PubChem CID: 22595194
Chemical data
Formula C16H20BrNO2
Molecular mass 338.240 g/mol
  • Brc1ccc(cc1)[C@H]2C[C@@H]3N(C)[C@H]([C@H]2C(=O)OC)CC3
  • 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 N
  • Key:HNVGNUVAMRLMSG-KBXIAJHMSA-N N
 NYesY (what is this?)  (verify)

(–)-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
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 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 from rats brains (1995). More recent work has advocated using cloned human transporter/s.

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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