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Dalmatian pyrethrum (Tanacetum cinerariifolium /Trevir./ Sch. Bip.) synthesizes secondary metabolite pyrethrin, known for its potent insecticidal and repellent activity. The present study was aimed at optimizing the maceration extraction parameters that improve the efficiency of pyrethrin extraction from the dried Dalmatian pyrethrum flower heads. Extraction efficiencies under several conditions were investigated: different solvent types, extraction time, the rotational speed of the stirrer, and the solvent volume. The highest recovery values were obtained with 5 mL of acetone, at the rotational speed of 400 rpm, and the extraction time of three hours. In addition, the extraction efficiency of maceration was compared to that of ultrasound-assisted and matrix solid phase dispersion extraction, both previously optimized for pyrethrin extraction. The extractions were carried out on samples of three natural Dalmatian pyrethrum populations (Krk, Mt. Kozjak, and Senj). Both the total pyrethrin content and the HPLC profile varied between different extraction techniques. Across applied methods, the highest efficiency was observed with matrix solid phase dispersion extraction. Evaluation of the differences between data obtained using different extraction techniques was performed by the Bland-Altman analysis, revealing good agreement between the three methods.