Pharma & Specialty Chemical Standards

Bupivacaine, IUPAC name 1-butyl-N-(2,6-dimethylphenyl)-4-piperidinamine, is a synthetic amide-linked local anesthetic with molecular formula C18H28N2O and molecular weight 288.44 g/mol. Structurally, it features a 2,6-dimethylphenyl ring, a piperidine moiety connected via an amide bond, and a terminal butyl group. Therapeutically, it is used for spinal, epidural, and peripheral nerve blocks. Its physicochemical properties include a pKa of ~8.1, enabling lipid solubility (log P ~2.5) and prolonged tissue retention. Mechanistically, bupivacaine inhibits voltage-gated sodium channels by binding to open states, preventing depolarization and nerve impulse transmission. Its high potency and duration are attributed to its structural rigidity and slow dissociation from sodium channels.