We begin by revisiting the so-called Caldirola - Kanai Hamiltonian and discuss its inherent ambiguity: does it represent a dissipative harmonic oscillator (HO) subject to a friction force, or does it describe an HO with a time-dependent mass (TDM)? Although classically both descriptions do coexist, in the quantum domain the solution of the Schrodinger equation (or Heisenberg equations of motion) with a TDM does not present inconsistencies, however, the dissipative Hamiltonian shows violation of the Heisenberg uncertainty principle. This violation is avoided by introducing a stochastic force in the equations of motion, which will take care of the fluctuations due to the environment. Once the distinction between the dissipative and amplifying Hamiltonian is made clear, we consider the problem of the quantum TDM HO subject to dissipation, showing that both phenomena may be merged and described by a single Hamiltonian, the amplifying - dissipative Hamiltonian. We obtain the solutions of the Heisenberg equations of motion for the canonical momentum and position; next, we specialize on the weak damping limit and analyse the effects of the amplifying - dissipative process on the mean values of the physical variables.