Pineapple weed (Matricaria discoidea DC.) is a widely spread plant in Europe and North America. In ethnomedicine, it is well known for its anti-inflammatory and spasmolytic activity. The aim of the research was to develop novel methods of M. discoidea herb complex processing for creating the essential oil and the dry extracts and to investigate their phytochemical composition. Moreo-ver, the molecular docking of main substances and in vivo their soporific and analgesic activity were studied. The essential oil and two dry extracts from M. discoidea were prepared. Total 16 phenolic compounds (7 flavonoids, 7 hydroxycinnamic, 2 phenolic acids) in the dry extracts were identified by means of UPLC-MS/MS. In the essential oil 9 main terpenoids were identified by gas chromatography (GC). We showed that the phenolics extraction from the present herb was successful by using 70% ethanol in a triple extraction and in the range of 1:14-1:16. The in-vivo studies with rodents showed analgesic activity of M. discoidea extracts and the improvements in the sleep of animals. The dry extracts of M. discoidea herb did not show any toxicity. The molecular docking showed the high probability of COX-1,2 inhibition and NMDA receptor antagonism induced by the extracts.