Morphine studied by vibrational spectroscopy and DFT calculations

Barańska, Małgorzata; Kaczor, Agnieszka

doi:10.1002/jrs.3005

Cited by 22 publications

(19 citation statements)

References 19 publications

(17 reference statements)

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“…Cinchona alkaloids have already been studied by some chromatographic and fluorescence methods; however, only a few seem to be of great importance: TLC and HPLC with fluorescence detection or densitometric evaluation, stereoselective non aqueous capillary electrophoresis, fluorescence life‐time determination, and circular dichroism . On the other hand, some studies have already shown usefulness of vibrational spectroscopy for identification and determination of isolated alkaloids and for the localization of these alkaloids in plants and related products, including the application of Vibrational Optical Activity (VOA) methods . Furthermore, because compounds like QN and QND show different properties in their pharmaceutical usage, it seems to be vitally important to differentiate between the individual pseudoenantiomers.…”

Section: Introductionmentioning

confidence: 99%

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Roman

Chruszcz‐Lipska

Barańska

2015

J Raman Spectroscopy

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Cinchona alkaloids are well-known antimalarial compounds also used in asymmetric synthesis in organic chemistry. In this work, vibrational spectra of quinine, quinidine, cinchonine, and cinchonidine were acquired and interpreted on the basis of theoretical calculations. Normal Raman spectra of the alkaloids in solution exhibit similar patterns and cannot be used for differentiation between the derivatives (e.g. quinine and cinchonidine) and corresponding pseudoenantiomers (e.g. quinine and quinidine). Thus, Raman Optical Activity (ROA) method was applied to show distinct differences related to the configuration of chiral atoms. ROA allowed unequivocal identification of the pseudoenantiomers based on the sign of the characteristic bands from a single measurement. The experiments were supported by the theoretical approach including conformational study followed by wavenumber calculations and Potential Energy Distribution (PED) analysis. For quinine, vibrational spectroscopy was additionally used to show its structural changes in aqueous solutions at various pH and its distribution in a pharmaceutical product. Spatial distribution of quinine in a drug was observed by the FT-Raman mapping technique.

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Section: Introductionmentioning

confidence: 99%

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Roman

Chruszcz‐Lipska

Barańska

2015

J Raman Spectroscopy

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“…For this experiment, we particularly tracked the spectral region associated with OH functional group being our unique vibrational band marker associated with the template (morphine). The typical vibrational bands of morphine were given the following assignments based on literature: strong signal at 1050–1200 cm −1 is due to COC stretching vibrations; 1600–1700 cm −1 is due to the skeletal vibration of CC; 2800–3000 cm −1 is due to CH stretching and deformation vibration; and 3200–3600 cm −1 a strong vibration is due to OH stretch . The peak at 1600–1700 cm −1 is due to the CC vibration of morphine that overlaps with CO present in our cross‐linker (MBA).…”

Section: Resultsmentioning

confidence: 93%

“…The typical vibrational bands of morphine were given the following assignments based on literature: strong signal at 1050-1200 cm −1 is due to C O C stretching vibrations; 1600-1700 cm −1 is due to the skeletal vibration of C C ; 2800-3000 cm −1 is due to C H stretching and deformation vibration; and 3200-3600 cm −1 a strong vibration is due to OH stretch. [ 58,59 ] The peak at 1600-1700 cm −1 is due to the C C vibration of morphine that overlaps with C O present in our cross-linker (MBA). Likewise, the peaks at 1050-1200 cm −1 are due to C O C stretching vibrations of morphine that overlaps with the C H out-of-plane deformation from poly( p -AS).…”

Section: Functional Group Characterization and Template Removal Studimentioning

confidence: 98%

Capacitive Detection of Morphine via Cathodically Electropolymerized, Molecularly Imprinted Poly(p‐aminostyrene) Films

Vergara

Pernites

Tiu

et al. 2016

Macro Chemistry & Physics

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Highly sensitive and selective detection of morphine is exhibited using a capacitive transducer coated with cathodically electropolymerized and molecularly imprinted poly(p aminostyrene). Through molecular imprinting, morphine‐specific recognition sites have been fabricated throughout the film, which shows exceptional binding activity toward morphine based from electrochemical capacitance measurements. The thin film sensor has a linear response to morphine solutions with 20–40 × 10−6 m concentrations and a detection limit of 5.95 × 10−6 m. It demonstrates high selectivity toward morphine as compared to other analog molecules including nicotine and cholesterol. The formation of the polymer film is facilitated and monitored using electrochemical‐quartz crystal microbalance and characterized by X‐ray photoelectron spectroscopy. Infrared spectroscopy confirms the loading and removal of the analyte from the film. Based on molecular modeling calculations, strong hydrogen‐bonding interactions between the monomer, cross‐linker, and analyte form a stable pre‐polymerization complex, which is critical in successfully imprinting morphine into the film and effective sensing of the analyte.

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“…Nondestructive analysis of toxic substances has been carried out using vibrational spectroscopy—Raman and Fourier transform infrared spectroscopy (FTIR). Both are fast techniques that can obtain spectra without using reagents for small samples, permit to the use of portable devices and optical fibers for remote analysis, and identify substances quickly . Vibrational spectroscopy techniques are based on the fact that chemical bonds of substances have specific vibration frequencies that correspond to the vibrational energy levels of the molecule.…”

Section: Introductionmentioning

confidence: 99%

“…Both are fast techniques that can obtain spectra without using reagents for small samples, permit to the use of portable devices and optical fibers for remote analysis, and identify substances quickly. [11,12] Vibrational spectroscopy techniques are based on the fact that chemical bonds of substances have specific vibration frequencies that correspond to the vibrational energy levels of the molecule. Although Raman spectroscopy is based on the inelastic scattering of photons by molecules as a function of excitation by ultraviolet, visible, or infrared radiation, FTIR spectroscopy is based on the absorption of infrared radiation by the molecule.…”

mentioning

confidence: 99%

Quantification of cocaine in ternary mixtures using partial least squares regression applied to Raman and Fourier transform infrared spectroscopy

Penido

Pacheco

Novotny

et al. 2017

J Raman Spectroscopy

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The use of chemicals is often related to suicide attempts and acute poisoning, which account for a significant number of hospital admissions. The differential diagnosis of patients exposed to poisoning is intricate and varies according to the substance used. The identification of drugs and drug abuse in cases of poisoning often requires time‐consuming and complex techniques, such as chromatography. The use of vibrational spectroscopy such as Raman spectroscopy and Fourier transform infrared spectroscopy (FTIR) enables the quick identification of toxic substances using no reagents or markers. This study aims to apply these techniques in the long term to identify and quantify substances found at the locations of suicide attempts, poisonings, and even drug consumption sites, including crack samples containing a cocaine base and adulterants commonly seized in drug busts, such as caffeine, lidocaine, and sodium carbonate. In this study, Raman and FTIR spectra of ternary mixtures of crack with caffeine and sodium carbonate and crack with lidocaine and sodium carbonate were obtained. These spectra were used for building multivariate models based on partial least squares (PLS) for determining the composition of the samples quantitatively. High correlation coefficients (r > 0.98) and small cross‐validation prediction errors (< 6%) were obtained for both Raman and FTIR spectral models. The results showed that PLS regression enables crack quantification in ternary mixtures using both Raman and FTIR spectroscopy, allowing for quick medical intervention or determination of the cause of death in cases of cocaine toxicity.

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Morphine studied by vibrational spectroscopy and DFT calculations

Cited by 22 publications

References 19 publications

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Capacitive Detection of Morphine via Cathodically Electropolymerized, Molecularly Imprinted Poly(p‐aminostyrene) Films

Quantification of cocaine in ternary mixtures using partial least squares regression applied to Raman and Fourier transform infrared spectroscopy

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