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4′-Fluorococaine

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Chemical compound Pharmaceutical compound
4′-Fluorococaine
Legal status
Legal status
Identifiers
IUPAC name
  • methyl (1R,2R,3S,5S)-3-(4-fluorobenzoyloxy)-8-methyl-8-azabicyclo octane-2-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20FNO4
Molar mass321.348 g·mol
3D model (JSmol)
SMILES
  • CN12CC1((C2)OC(=O)C3=CC=C(C=C3)F)C(=O)OC
InChI
  • 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
  • Key:JRPRINGETIYVSV-ZQDZILKHSA-N
  (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.

See also

References

  1. Gatley SJ, Yu DW, Fowler JS, MacGregor RR, Schlyer DJ, Dewey SL, et al. (March 1994). "Studies with differentially labeled cocaine, norcocaine, benzoylecgonine, and - and 4'-fluorococaine to probe the extent to which cocaine metabolites contribute to PET images of the baboon brain". Journal of Neurochemistry. 62 (3): 1154–62. doi:10.1046/j.1471-4159.1994.62031154.x. PMID 8113802. S2CID 25854431.
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ATC code: N06B


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