This study investigates the synergism of licorice with two herbs (Bupleurum chinense and Zingiberis officinalis) commonly used in Classical Chinese Medicine. Each sample was decocted in de-ionized water for one hour at 100 °C. Individual and paired decoctions were analyzed using High Performance Liquid Chromatography (HPLC) to evaluate differences in chemical signatures between extractions. Chemical constituent concentration varied between single herb and paired herb decoctions. In the paired decoctions, many chemical peaks increased in concentration. Interestingly, other peaks decreased in concentration, though none disappeared. This preliminary data demonstrate that paired herbal decoctions contain increased levels of active components. Furthermore, a decrease in peaks within the paired decoction but not in the individual formulas suggests that herb decoctions generated new chemical structures. This study represents foundational research into synergistic relationships between herbs.