Investigation of structure, vibrational and NMR spectra of oxycodone and naltrexone: A combined experimental and theoretical study

Tavakol, Hossein; Esfandyari, Maryam; Taheri, Salman; Heydari, Akbar

doi:10.1016/j.saa.2011.03.038

Cited by 15 publications

(4 citation statements)

References 54 publications

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“…These calculations were carried out using DFT with ωB97XD/6-31+G* level of theory. DFT calculation has shown high abilities in the calculation of molecular [24] and spectral [25,26] properties of chemical structures, comparable with MP2 methods [27,28], in addition to their acceptable results in prediction of thermodynamic and kinetic properties of chemical phenomena [29][30][31]. Moreover, among various DFT methods, ωB97XD has been designed as the best DFT code to interpret the intermolecular interactions.…”

Section: Methodsmentioning

confidence: 99%

The Effect of Doping Different Heteroatoms on the Interaction and Adsorption Abilities of Fullerene

Amiraslanzadeh

2015

Heteroatom Chemistry

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Density functional method has been employed to compare the interaction and adsorption abilities of simple and doped fullerenes with various heteroatoms (Al, B, Si, N, P, and S). Three sulfur‐containing molecules (H2S, SO2, and thiophene) were selected to study of their interactions with fullerenes. These interactions will be important in the design of new sensor, adsorption, and elimination of pollutants and chemical reactions. The calculated adsorption energies (Ead) in the gas phase and solvents (water, using the polarized continuum model) showed that all adsorbates have exothermic interaction with all fullerenes. The maximum Ead values were calculated for aluminum‐doped fullerene (AF) and nitrogen‐doped fullerene (NF), and the adsorption energies in solvent are not so different with those in the gas phase. Natural Bond Orbitals (NBO) calculations showed the complexes of AF and then boron‐doped fullerene (BF) have the highest E2 interaction energies, whereas simple fullerene (F) and phosphorus‐doped fullerene (PF) have the least E2 energies. Population analyses showed that doping by heteroatoms bearing extra electrons reduces the energy gap and this decrease is more than the decrease observed from doping by heteroatoms with electron defect. Moreover, the change in the energy gaps of the complexes, obtained from the density of states (DOSs) plots, showed that these structures could be used in sensor devices. All calculated data confirmed the better adsorption of SO2 by fullerenes versus H2S and thiophene and among all fullerenes, AF and then BF and NF are the best adsorbent for these structures.

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Section: Methodsmentioning

confidence: 99%

The Effect of Doping Different Heteroatoms on the Interaction and Adsorption Abilities of Fullerene

Amiraslanzadeh

2015

Heteroatom Chemistry

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“…There are also absorption regions at 1132 and 1217 cm -1 related to cyclopropane C−H and C−C scissor bends, respectively. 36 The IR absorption spectra for BUP has a band at 1553 cm -1 related to an out-of-plane deformation of the amide N−H bond; a peak at 1687 cm -1 related to the ketone C=O bond stretching vibration; a peak at 902 cm -1 related to the R 2 NH bond; a peak at 1235 cm -1 from C−Cl bond vibration; and a peak at 1457 cm -1 indicating C−C bond stretching of the aromatic ring. 37…”

Section: Resultsmentioning

confidence: 99%

A Mid-Infrared Spectrophotometric Method for Simultaneous Quantification of Naltrexone and Bupropion with Multivariate Calibration

Novack¹,

Cobre²,

Madeira³

et al. 2023

J. Braz. Chem. Soc.

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Naltrexone (NTX) and bupropion (BUP) are used in combination in clinical practice for obesity; however, the existing analytical methods for this drug combination are not sustainable. This work aims to develop an analytical method that is faster, easier and less expensive compared with high performance liquid chromatography (HPLC) and involves green technology without solvents to quantify BUP and NTX in combination. The objective was to validate a method using mid-infrared (MIR) spectroscopy associated with multivariate calibration and chemometrics to simultaneously measure NTX and BUP in a pharmaceutical capsule form. The models were developed using MIR spectroscopy with diffuse reflectance, with interval partial least squares (iPLS) variable selection. The working range selected to optimize the model was from 1885.8 to 1585.4 cm-1. The chosen model was obtained with partial least squares (PLS2) and with data pre-processed by first derivative Savitzky-Golay smoothing followed by mean centering, using four latent variables, providing a root mean square error of prediction of 1.8 mg g-1 for NTX and 6.42 mg g-1 for BUP. The method was validated according to current international standards. In conclusion, the methods developed in the MIR region provided statistically similar results to the validated chromatographic method for commercial pharmaceutical formulations.

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“…The main differences between normal Raman and SERS spectra for oxycodone are the enhanced intensities of the Raman bands in the latter at 580 and 1279 cm −1 relative to the former. The most intense peaks in the SERS Raman spectra of oxycodone are found at 613, 638, 1279 and 1450 cm −1 , and they involve C‐C‐C and C‐C‐H bending, and CH 2 bending and stretching [24] In the fingerprint region beyond 1450 cm ‐1 , the most intense bands are found at 1616, 1640 and 1735 cm −1 and correspond to stretching vibrations of the aromatic ring and the carbonyl, respectively [24]…”

Section: Resultsmentioning

confidence: 99%

Trace level detection of select opioids (fentanyl, hydrocodone, oxycodone, and tramadol) in suspect pharmaceutical tablets using surface‐enhanced Raman scattering (SERS) with handheld devices

Kimani

Lanzarotta

Batson

2020

Journal of Forensic Sciences

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The opioid crisis in the USA has resulted in over 702,000 overdose fatalities between 1999 and 2017 and can be attributed to over‐prescription of opioids and abuse of synthetic opioids in combination with other illicit drugs. A rapid and sensitive SERS method has been developed for trace detection of opioids including fentanyl, hydrocodone, oxycodone, and tramadol in low‐dosage suspect tablets using two different handheld Raman spectrometers equipped with 785 and 1064 nm lasers. The method involves a micro‐extraction procedure using 10% methanol in deionized water, followed by filtration and addition of colloidal silver and aqueous KBr, resulting in a mixture that can be measured directly via a glass vial. The lowest concentration (Cmin) of fentanyl, tramadol, oxycodone, and hydrocodone standards that yielded a positive match was 250 ng/ml, 5, 10, and 10 μg/ml using the 1064 nm laser device and 100 ng/ml, 1 μg/ml, 500 ng/ml, and 750 ng/ml using the 785 nm laser device, respectively. For the analysis of suspect tablets containing these opioids, the Cmin ranges between 5 and 75 µg/ml for 1064 nm laser device and 1 and 50 µg/ml for 785 nm laser device. The overall positive identification rate for all the opioids studied in the suspect counterfeit tablets analyzed ranged from 80% to 100%. The use of SERS for rapid chemical identification at remote sampling sites, such as international mail facilities (IMFs) and express courier hubs (ECHs), provides a rugged, simple, and practical method applicable for point‐of‐entry sampling and analysis.

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Investigation of structure, vibrational and NMR spectra of oxycodone and naltrexone: A combined experimental and theoretical study

Cited by 15 publications

References 54 publications

The Effect of Doping Different Heteroatoms on the Interaction and Adsorption Abilities of Fullerene

The Effect of Doping Different Heteroatoms on the Interaction and Adsorption Abilities of Fullerene

A Mid-Infrared Spectrophotometric Method for Simultaneous Quantification of Naltrexone and Bupropion with Multivariate Calibration

Trace level detection of select opioids (fentanyl, hydrocodone, oxycodone, and tramadol) in suspect pharmaceutical tablets using surface‐enhanced Raman scattering (SERS) with handheld devices

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