Raman spectroscopy under high pressures up to 10 GPa and density functional computations up to 30 GPa are combined to obtain insights into the behavior of a prototypical nanohoop conjugated molecule, cycloparaphenylene, CPP. Upon increasing pressure the nanohoop undergoes deformations, first reversible ovalization and then at even higher pressures aggregates are formed. This irreversible aggregation is due to the formation new intermolecular σ-bonds. Frequencies and derivatives of the Raman frequency shifts as a function of pressure are well reproduced by the computations. The frequency behavior is tied to changes in aromatic/quinonoid characters of the nanohoop. The modeling at moderate high pressures reveals the deformation of the CPP molecules into oval-like and peanut-like shapes. Surprisingly the pressure derivatives of the observed Raman mode shifts undergo a sudden change around a pressure value that is common to all Raman modes, indicating an underlying geometrical change extended over the whole molecule that is interpreted by the computational modeling. Simulations predict that under even larger deformations caused by higher pressures, oligomerization chemical reactions would be triggered. Our simulations demonstrate that these transformations would occur regardless of the solvent, however pressures at which they happen are influenced by solvent molecules encapsulated in the interior of the CPP.