Synthesis of two radiofluorinated cocaine analogues using distilled 2-[18F]fluoroethyl bromide.
Two fluorinated congeners of cocaine, 2'-fluoroethyl (1R-2-exo-3-exo)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octane- 2-carboxylate (FETT) and its 4-chlorophenyl analogue (FECT) were synthesized. Radiolabelling with 18F was achieved by O-[18F]fluoroalkylation of the corresponding carboxylic acid salts with distilled 2-[18F]fluoroethyl bromide in DMF. After HPLC purification, yields of radiochemically pure, formulated products were 22-30% (not corrected for decay) in a synthesis time of 60-70 min. The use of distilled 2-[18F]fluoroethyl bromide was indispensable for the reliable production of pure products.
Wilson
A A
AA
PET Centre, Clarke Institute of Psychiatry, University of Toronto, Faculty of Medicine, ON, Canada.
Dasilva
J N
JN
Houle
S
S
D001692:Biological Transport; D003042:Cocaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004298:Dopamine / Q000378:metabolism; D005462:Fluorine Radioisotopes; D005466:Fluorocarbons; D006801:Humans; D007202:Indicators and Reagents; D007553:Isotope Labeling / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D014055:Tomography, Emission-Computed
C095071:2'-fluoroethyl 8-methyl-3-(4-chlorophenyl)-8-azabicyclo(3.2.1)octane-2-carboxylate; C095070:2'-fluoroethyl 8-methyl-3-(4-methylphenyl)-8-azabicyclo(3.2.1)octane-2-carboxylate; D005462:Fluorine Radioisotopes; D005466:Fluorocarbons; D007202:Indicators and Reagents; C095069:2-fluoroethyl bromide; D003042:Cocaine; D004298:Dopamine