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Background: A critical review of the literature demonstrates that masticatory apparatus with an artificial oral environment is of interest in the fields including (i) dental science; (ii) food science; (iii) the pharmaceutical industries for drug release. However, apparatus that closely mimics human chewing and oral conditions has yet to be realised. This study investigates the vital role of dental morphology and form–function connections using two-bite test parameters for effective drug release from medicated chewing gum (MCG) and compares them to human chewing efficiency with the aid of a humanoid chewing robot and a bionics product lifecycle management (PLM) framework with built-in reverse biomimetics—both developed by the first author. Methods: A novel, bio-engineered two-bite testbed is created for two testing machines with compression and torsion capabilities to conduct two-bite tests for evaluating the mechanical properties of MCGs. Results: Experimental studies are conducted to investigate the relationship between biting force and crushing/shearing and understand chewing efficiency and effective mastication. This is with respect to mechanochemistry and power stroke for disrupting mechanical bonds releasing the active pharmaceutical ingredients (APIs) of MCGs. The manuscript discusses the effect and the critical role that jaw physiology, dental morphology, the Bennett angle of mandible (BA) and the Frankfort-mandibular plane angle (FMA) on two-bite test parameters when FMA = 0, 25 or 29.1 and BA = 0 or 8. Conclusions: The impact on other scientific fields is also explored. Full article