Calculation of the UV Spectrum and Electrophilic Reactive Sites of Fentanyl Molecule Based on the Density Functional The
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TRUCTURE OF MATTER AND QUANTUM CHEMISTRY
Calculation of the UV Spectrum and Electrophilic Reactive Sites of Fentanyl Molecule Based on the Density Functional Theory Bin Shia,*, Jiancheng Yua, Tianyu Tanga, Li Yuana, and Yanlin Tanga,** aSchool
of Physics, Guizhou University, Guiyang, 550025 China *e-mail: [email protected] **e-mail: [email protected]
Received July 15, 2019; revised January 22, 2020; accepted May 19, 2020
Abstract—The theoretical calculation of fentanyl molecule based on DFT is of great significance to understand the properties. The initial conformations were searched by molclus software and two reasonable conformations were selected. The structural optimization of fentanyl using DFT/B3LYP/6-311+G(d,p) method by Gaussian16. Based on this, the first 50 excited states are calculated by using TD-DFT with methanol as the solvent. Multiwfn 3.6 was used to calculate its electrical parameters such as electrostatic potential, average local ionization energy, Fukui function and dual descriptor and draw UV spectrum. From the UV spectrum, the maximum absorption peak is located at 188 nm, which is mainly formed by the σ → σ* transition of the C–C, C–H bond. From the analysis of electrical parameters, the nitrogen atom (N18) on the piperidine ring is an electrophilic reactive site, and it is easily attacked by an electrophilic reagent so that the phenethyl group is replaced by a hydrogen atom to form norfentanyl. Keywords: fentanyl, density functional theory, UV spectrum, electrical parameters DOI: 10.1134/S0036024420120055
INTRODUCTION Being a powerful opioid analgesic, fentanyl is the most widely used synthetic opioid in medicine. It is suitable for analgesia in various surgical operations and can also be used as an anesthesia adjuvant. It is characterized by rapid onset of action, extremely short duration of action, strong drug efficacy and low side effects [1]. Fentanyl is 100–180 times more potent than morphine [2, 3], 50 times more potent than heroin, and has fewer side effects than morphine and less respiratory inhibition. At present, fentanyl has been illegally abused as a recreational drug and has become an important member of synthetic drugs. Excessive use of fentanyl can lead to addiction, respiratory depression and even death [4, 5]. Therefore, fentanyl is now a national controlled drug. Fentanyl has received increasing attention due to its use in analgesia and respiratory inhibition toxicity. At present, the research on fentanyl mainly focuses on the experiments and applications of clinical medicine and pharmacy, as well as the synthesis and testing methods of fentanyl and related derivatives [6–8]. Using the method of quantum chemistry [9–11], Chen et al. analyzed the electrostatic potential on fentanyl compounds surface [12]. Li et al. used molecular dynamics to simulate the interaction of fentanyl compounds with opioid receptors [13]. The reactive site of a molecule reflects the ability of each
group in the molecule to participate in a chemical reaction. Cao et al. compared different methods for p
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