The aporia is obvious: food supplement, classified and regulated by food law, sometimes have the characteristics and the typical effects of medicines. In addition, these are produced by pharmaceutical companies and, through the scientific officer, are prescribed by doctors and dispensed by pharmacies. This study will attempt to retrace the winding, and sometimes overlapping, regulatory pathways of the legislation on food supplement, food and medicines. It will be important object the particular application of the precautionary principle behind the legislation on food supplement: application "in posterior", so the controls on the purity of the product and the possible effects resulting from the assumption is carried out ex post trade. So we try to disentangle the intricate legislation with the national (and European) Court contributions. In particular, after a brief analysis of the rulings of the Competition and Market Authority on misleading advertising and by the Supreme Court in relation to crimes against health damage, it will come to the analysis of interpretative problems of a purely criminal law nature, in light of the recent proposal for reform about agribusiness crimes. Finally, it will be inevitable to analyze briefly the recent implementation of the d.lgs. n. 17/2004 concerning the distance trade of non-prescription medicines. There is no doubt that now, internet represents the preferred distribution channel for pharmaceutical products (including food supplement) and the most tempting "place" (because of control difficulties) for the realization of criminal conduct. The conclusion will be that the need to achieve more targeted and homogeneous regulatory measures, while also having to protect - public and individual - health through the protection of the legal security in one with the protection of the right to information.