Novel synthesis of [1‐11C]γ‐vinyl‐γ‐aminobutyric acid ([1–11C]GVG) for pharmacokinetic studies of addiction treatment

γ‐Vinyl‐γ‐aminobutyric acid (GVG, Vigabatrin^®), a suicide inhibitor of GABA‐transaminase (GABA‐T), has been suggested as a new drug for the treatment of substance abuse. In order to better understand its pharmacokinetics and potential side effects, we have developed a radiosynthesis of carbon‐11 (t_1/2=20 min) labeled GVG for positron emission tomographic (PET) studies. We report here a novel synthetic strategy to prepare the precursor and to efficiently label GVG with C‐11. 5‐Bromo‐3‐(carbobenzyloxy)amino‐1‐pentene was synthesized in five steps from homoserine lactone, including reduction and methylenation. This was used in a one‐pot, two‐step radiosynthesis. Displacement of bromide with no‐carrier‐added ¹¹C]cyanide followed by acid hydrolysis afforded 1‐¹¹C]GVG with decay corrected radiochemical yields of 27±9% (n=6, not optimized) with respect to ¹¹C]cyanide in a synthesis time of 45 min. Copyright © 2002 John Wiley & Sons, Ltd.