Synthesis of two radiofluorinated cocaine analogues using distilled 2-[18F]fluoroethyl bromide

Appl Radiat Isot. 1995 Aug;46(8):765-70. doi: 10.1016/0969-8043(95)00028-c.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Transport
  • Cocaine / analogs & derivatives*
  • Cocaine / chemical synthesis
  • Dopamine / metabolism
  • Fluorine Radioisotopes*
  • Fluorocarbons*
  • Humans
  • Indicators and Reagents
  • Isotope Labeling / methods
  • Models, Molecular
  • Molecular Structure
  • Tomography, Emission-Computed

Substances

  • 2'-fluoroethyl 8-methyl-3-(4-chlorophenyl)-8-azabicyclo(3.2.1)octane-2-carboxylate
  • 2'-fluoroethyl 8-methyl-3-(4-methylphenyl)-8-azabicyclo(3.2.1)octane-2-carboxylate
  • Fluorine Radioisotopes
  • Fluorocarbons
  • Indicators and Reagents
  • 2-fluoroethyl bromide
  • Cocaine
  • Dopamine