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In this work, the conformational flexibility of melatonin was investigated using correlated ab initio<\/jats:italic> calculations. Conformers, obtained previously at the Hartree\u2010Fock level (HF\/6\u201031G*), were fully optimized using second order M\u00f8ller\u2010Plesset perturbation theory applying the frozen core approximation (MP2(FC)\/6\u201031G*). Furthermore, single\u2010point MP4(SDQ,FC)\/6\u201031G*\/\/MP2(FC)\/6\u201031G* computations were performed to investigate the effect of higher order perturbation terms. The HF and MP2 conformational spaces are considerably different: the initial 128 structures converged into 102 different local minima as confirmed by frequency calculations; 28 new minima appeared and 26 previous HF local minima disappeared; no \u201call\u2010trans\u201d C3 side chain conformations are seen at the MP2(FC) level. The MP2 global minimum conformation is stabilized by an aromatic\u2010side chain interaction. \u00a9 2008 Wiley Periodicals, Inc. 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