Bupivacaine has a chiral centre and is currently available as a racemic mixture of its two enantiomers: R(+)-bupivacaine and S(-)-bupivacaine. Preclinical studies have demonstrated that there is enantiomer selectivity of action with the bulk of central nervous system and cardiovascular toxicity residing with the R(+) isomer. The aim of this study was to compare the clinical efficacy and safety of S(-)-bupivacaine with racemic RS-bupivacaine for extradural anaesthesia. We studied 88 patients undergoing elective lower limb surgery under lumbar extradural anaesthesia who received 15 ml of 0.5% or 0.75% S(-)-bupivacaine, or 0.5% RS-bupivacaine in a randomized, double-blind study. There was no difference in onset time, maximum spread of sensory block or intensity of motor block between the three groups. Duration of sensory block was significantly longer for 0.75% S(-)-bupivacaine. We conclude that S(-)-bupivacaine has similar local anaesthetic characteristics to RS-bupivacaine when used for extradural anaesthesia.