title: Investigation of structure, vibrational and NMR spectra of oxycodone and naltrexone: a combined experimental and theoretical study.
abstract: In this work, two important opioid antagonists, naltrexone and oxycodone, were prepared from thebaine and were characterized by IR, (1)H NMR and (13)C NMR spectroscopy. Moreover, computational NMR and IR parameters were obtained using density functional theory (DFT) at B3LYP/6-311++G** level of theory. Complete NMR and vibrational assignment were carried out using the observed and calculated spectra. The IR frequencies and NMR chemical shifts, determined experimentally, were compared with those obtained theoretically from DFT calculations, showed good agreements. The RMS errors observed between experimental and calculated data for the IR absorptions are 85 and 105 cm(-1), for the (1)H NMR peaks are 0.87 and 0.17 ppm and for those of (13)C NMR are 5.6 and 5.3 ppm, respectively for naltrexone and oxycodone.
authors.affiliation: Chemistry Department, Faculty of Science, University of Zabol, Mofatteh street, Zabol, Iran. h_tavakol@uoz.ac.ir
authors.forename: Hossein
authors.initials: H
authors.lastname: Tavakol
authors.forename: Maryam
authors.initials: M
authors.lastname: Esfandyari
authors.forename: Salman
authors.initials: S
authors.lastname: Taheri
authors.forename: Akbar
authors.initials: A
authors.lastname: Heydari
mesh_terms: D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009271:Naltrexone / Q000737:chemistry*; D009292:Narcotic Antagonists / Q000737:chemistry*; D010098:Oxycodone / Q000737:chemistry*; D011789:Quantum Theory; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman
chemical_list: D009292:Narcotic Antagonists; D009271:Naltrexone; D010098:Oxycodone