DFT characterization of MDMA methylene homologue, a chemical compound with psychoactive properties

Gosav, Steluța; Ion, Adelina; Praisler, Mirela

doi:10.1063/1.5091392

Cited by 8 publications

(7 citation statements)

References 6 publications

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“…The chemical potential of genistein compound was evaluated using a series of electronic parameters, such as the dipole moment (DM), the energy of the highest occupied molecular orbital (E HOMO ) and the energy of the lowest unoccupied molecular orbital (E LUMO ), which were extracted from the .log output file of the Gaussian 09 program, and the gap energy (Egap), the ionization potential (IP), the electron affinity (EA), the chemical hardness (η), the chemical softness (σ), the electronegativity (χ) and electrophilic index (ω), which were calculated using specific formulas [54][55][56]. The .chk output file of the Gaussian 09 program was used as the input file for Avogadro program (Compiling Avogadro on Linux, http://avogadro.openmolecules2012, accessed on 18 March 2022) to represent the frontier molecular orbitals i.e., HOMO and LUMO, and the molecular electrostatic potential (MEP) map of the genistein compound.…”

Section: Molecular Modelling Study Of Genisteinmentioning

confidence: 99%

“…The dipole moment is a quantum parameter related to the charge distribution (charge separation) in a molecule. The magnitude of the dipole electric moment influences the ability of a molecule to pass through a cellular membrane [55]. A recent research paper [68], revealed that there is a relationship between the dipole moment and biological activity (antibacterial, antifungal, anticancer etc.)…”

Section: Molecular Modelling Study Of Genisteinmentioning

confidence: 99%

“…Thus, if the energy gap decreased, the reactivity of the molecule increased, due to the fact that the electron donating efficiency also increased. Therefore, a lower energy gap leads to an enhancement of the antioxidant properties of a compound [55,56]. In the case of genistein, the value of the E gap parameter, of 4.18 eV, indicated the fact that the genistein was a compound with a medium chemical reactivity and an important antioxidant character.…”

Section: Molecular Modelling Study Of Genisteinmentioning

confidence: 99%

“…It is known that the degree of conjugation and the planarity/non-planarity of a molecule have a great influence on the electric charge distribution of the frontier molecular orbitals [55]. In the case of genistein, the electric charge distribution of the HOMO orbital is along the entire molecular structure (Figure 10) due to the presence of the C2=C3 double bond, which allows a more pronounced delocalization of the electrical charge when switching from the HOMO molecular orbital to the LUMO molecular orbital.…”

Section: Molecular Modelling Study Of Genisteinmentioning

confidence: 99%

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Comparative Study of Natural Antioxidants from Glycine max, Anethum graveolensand Pimpinella anisum Seed and Sprout Extracts Obtained by Ultrasound-Assisted Extraction

et al. 2022

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The study aimed to evaluate the antioxidant potential of sprout and seed extracts from three species of plants, namely Glycine max (GMsp-sprouts, GMsd-seeds), Anethum graveolens (AGsp-sprouts, AGsd-seeds) and Pimpinella anisum (PAsp-sprouts, PAsd-seeds), which are widely accepted by consumers and have various applications in food flavoring, and also in natural medical treatments in the pharmaceutical industries. These plants are rich in valuable compounds that show a remarkable antioxidant power and are associated with many health benefits. Ethanol extracts were obtained by ultrasound-assisted extraction and they were comparatively evaluated for their in vitro antioxidant properties. The extracts were characterized by HPTLC, HPLC-DAD, total phenol content (TPC), total flavonoid content (TFC) analysis and antioxidant activities with different assays, such as total antioxidant capacity (TAC), 2,2′-azino-bis (3- ethylbenzothiazoline-6-sulfonic acid) radical cation decolorization assay (ABTS), 1,1-diphenyl 1-2-picryl-hydrazyl (DPPH) and iron binding ability of chelators. Our results showed that the sprout and seed extracts of the studied plants exhibited a high content of phytochemicals and promising antioxidant properties. The highest polyphenols content was detected for AGsd (53.02 ± 0.57 mg/g DW), PAsd (48.75 ± 0.34 mg/g DW) and the highest flavonoids content for PAsp (26.84 ± 0.57 mg/g DW). Moreover, the presence of valuable compounds was demonstrated by using HPTLC, FT-IR and HPLC-DAD techniques. In order to have a better understanding of the relationship between the biological properties and the electronic structure, a molecular modelling study of genistein was also conducted. Our approach to the comparative assessment of these three plant species was based on a priori knowledge from literature data; however, this study demonstrated that these plant extracts of seeds and also sprouts are excellent sources of natural antioxidants. Significant additional differences that were found in the phytochemical composition could be exploited in future research for pharmaceutical purposes.

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Section: Molecular Modelling Study Of Genisteinmentioning

confidence: 99%

Section: Molecular Modelling Study Of Genisteinmentioning

confidence: 99%

Section: Molecular Modelling Study Of Genisteinmentioning

confidence: 99%

Section: Molecular Modelling Study Of Genisteinmentioning

confidence: 99%

See 2 more Smart Citations

Comparative Study of Natural Antioxidants from Glycine max, Anethum graveolensand Pimpinella anisum Seed and Sprout Extracts Obtained by Ultrasound-Assisted Extraction

et al. 2022

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“…Studies have simulated CBL and CBG vibrational and electronic spectra for identification and characterization purposes . There are other examples in which the DFT has been applied to provide spectral properties for other NPS. − …”

Section: Introductionmentioning

confidence: 99%

In Silico Infrared Characterization of Synthetic Cannabinoids by Quantum Chemistry and Chemometrics

Castro

Rodrigues

Bruni

2020

J. Chem. Inf. Model.

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The concept of forensic sciences as mere trace analysis has been modified by the idea of forensic intelligence, which entails applying data to make decisions within the investigative process. Many countries are engaged in combating drug trafficking and drug use because they are related to public health and safety issues. Prohibiting the consumption of traditional drugs has led new psychoactive substances (NPSs) to emerge. NPSs consist of compounds that resemble the initially banned substance and which aim to mimic the traditional drug recreational effects while circumventing drug legislation. For example, synthetic cannabinoids are sprayed on herbal products to reproduce the cannabis recreational effects. According to the United Nations Office on Drugs and Crime (UNODC), the toxic effects of synthetic cannabis types are unknown, and harm and fatalities associated with the use of these drugs have been reported. Information on the characterization related to these species is lacking. The rate at which NPSs appear poses a significant challenge because employing conventional methods to understand the characteristics of these compounds may require time and be costly. This work uses in silico practices as an alternative to understand how NPSs related to cannabis behave. We apply quantum chemistry methods to evaluate several synthetic cannabinoids recognized in forensic samples. More specifically, we generate infrared spectra that can be employed as a benchmark for NPSs. We apply a multivariate classification to evaluate the results. We conclude that in silico methods are an alternative that provide information about the spectra of undetected substances. This information can help to identify new drugs, to increase knowledge about them, and to feed information procedures.

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Chemical Potential Evaluation of Kaempferol Based on Molecular Modeling

Paraschiv,

Gosav,

Praisler

2024

IFMBE Proceedings

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DFT characterization of MDMA methylene homologue, a chemical compound with psychoactive properties

Cited by 8 publications

References 6 publications

Comparative Study of Natural Antioxidants from Glycine max, Anethum graveolensand Pimpinella anisum Seed and Sprout Extracts Obtained by Ultrasound-Assisted Extraction

Comparative Study of Natural Antioxidants from Glycine max, Anethum graveolensand Pimpinella anisum Seed and Sprout Extracts Obtained by Ultrasound-Assisted Extraction

In Silico Infrared Characterization of Synthetic Cannabinoids by Quantum Chemistry and Chemometrics

Chemical Potential Evaluation of Kaempferol Based on Molecular Modeling

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