4′-Fluorococaine

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4′-Fluorococaine
Identifiers
  • methyl (1R,2R,3S,5S)-3-(4-fluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20FNO4
Molar mass321.343 g/mol g·mol−1
3D model (JSmol)
  • CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=C(C=C3)F)C(=O)OC
  • InChI=1S/C17H20FNO4/c1-19-12-7-8-13(19)15(17(21)22-2)14(9-12)23-16(20)10-3-5-11(18)6-4-10/h3-6,12-15H,7-9H2,1-2H3/t12-,13-,14-,15+/m0/s1 checkY
  • Key:JRPRINGETIYVSV-ZQDZILKHSA-N checkY
  (verify)

4′-Fluorococaine is a tropane derivative drug which is a synthetic analogue of cocaine. Unlike related compounds such as the corresponding 4′-fluorophenyltropane derivative CFT and the 2′-hydroxy analogue salicylmethylecgonine, 4′-fluorococaine has only around the same potency as cocaine as an inhibitor of dopamine reuptake, but conversely it is a much stronger serotonin reuptake inhibitor than cocaine, resulting in a significantly altered pharmacological profile in animal studies.[1]

See also

References

  1. ^ Gatley, S. J.; Yu, D. W.; Fowler, J. S.; MacGregor, R. R.; Schlyer, D. J.; Dewey, S. L.; Wolf, A. P.; Martin, T.; Shea, C. E.; Volkow, N. D. (2008). "Studies with Differentially Labeled [11C]Cocaine, [11C]Norcocaine, [11C]Benzoylecgonine, and [11C]-and 4′-[18F]Fluorococaine to Probe the Extent to Which [11C]Cocaine Metabolites Contribute to PET Images of the Baboon Brain". Journal of Neurochemistry. 62 (3): 1154–1162. doi:10.1046/j.1471-4159.1994.62031154.x. PMID 8113802.