The fluorescence quenching of 1,2,3,8-tetrahydro-1,2,3,3,8-pentamethyl-5-(trifluoromethyl)-7H-pyrrolo[3,2-g]quinolin-7-one (LD-473) by aromatic amines, namely, aniline, dimethyl aniline, and diethyl aniline, in methanol, ethanol, propanol, and butanol has been studied at room temperature using steady-state and time-resolved methods. A positive deviation from linearity has been observed in Stern–Volmer (S–V) plots. Various quenching rate parameters have been determined using the extended S–V equation and are found to be dependent on the dielectric constant of alcohols. The quenching ability of amines increases with increasing their ionization energies. Further, with the use of the sphere of action, static quenching model, and finite sink approximation model, it is concluded that the bimolecular quenching reactions are due to the combined effect of both dynamic and static quenching processes.