Structure determination of butylone as a new psychoactive substance using chiroptical and vibrational spectroscopies

Spálovská, Dita; Králík, František; Kohout, Michal; Jurásek, Bronislav; Habartová, Lucie; Kuchař, Martin; Setnička, Vladimı́r

doi:10.1002/chir.22825

Cited by 19 publications

(11 citation statements)

References 38 publications

(66 reference statements)

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“…ECD and VCD, combined with DFT calculations provided the AC of both enantiomers as ( S )-( 232 ) and ( R )-butylone ( 233 ) (Figure 64). 108…”

Section: Resultsmentioning

confidence: 99%

“…The AC of the compounds was established by VCD and X-ray diffraction. 63 Although icetexone (106) and conacytone (108) were originally isolated from Salvia ballotiflora in 1976, no detailed NMR assignment and AC determination were available. This was achieved by single-crystal X-ray studies of 106 and 108 ( Figure 28) whose Flack and Hooft parameters provided the AC.…”

Section: Monoterpenoids the Formulas Of The 28 Monoterpenoids Includmentioning

confidence: 99%

“…ECD and VCD, combined with DFT calculations provided the AC of both enantiomers as (S)-(232) and (R)-butylone (233) ( Figure 64). 108 A commercial sample of (−)-(3R,4R,5S)-oseltamivir (234) ( Figure 64) was stable for studies in chloroform, acetonitrile, and water solutions. ECD, ORD, VCD, and ROA, assisted by quantum chemical calculations pointed out different conformers, establishing thereby the most probable models responsible for structure-activity relationships (SAR).…”

Section: Nitrogenated Compoundsmentioning

confidence: 99%

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Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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Although demonstrated in 1975, vibrational circular dichroism (VCD) finally started to popularize during this century as a reliable tool to determine the absolute configuration (AC) of organic molecules. This research field continues to be a very dynamic one, in particular for the study of natural products which are a unlimited source of chiral molecules. It therefore turns of interest to summarize the accomplishments published in recent years and to comment on some eventual difficulties that emerged in rare cases to complete the AC determination task. Therefore the aim of this review is to update VCD results for the AC assignment of natural products published from 2015 to 2019, a period in which VCD was reported in some 126 publications involving almost 300 molecules. They are organized according the type of studied metabolite allowing an easily search. The molecules correspond to 28 monoterpenes concerning 17 papers, to 42 sesquiterpenes in 14 papers, to 51 diterpenes in 19 publications, to 5 other terpenoids in three papers, to 48 aromatic molecules in 15 reports, to 20 polyketides in 10 publications, to 27 miscellaneous formulas also in 10 papers, and to 76 nitrogen containing compounds, which include alkaloids and their synthetic analogs, in 38 articles. The landscape of reviewed molecules is quite wide as it goes from simple monoterpenes, like borneol or camphor, to very relevant biological molecules like the alkaloid cocaine or tadalafil samples to distinguish genuine and counterfeit Cialis®. In addition, 5 natural products and a simple derivative published outside the reviewed period, were used to illustrate some aspects of density functional theory calculations.

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“…ECD and VCD, combined with DFT calculations provided the AC of both enantiomers as ( S )-( 232 ) and ( R )-butylone ( 233 ) (Figure 64). 108…”

Section: Resultsmentioning

confidence: 99%

Section: Monoterpenoids the Formulas Of The 28 Monoterpenoids Includmentioning

confidence: 99%

Section: Nitrogenated Compoundsmentioning

confidence: 99%

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Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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“…The most prominent method for the separation of chiral substances nowadays is preparative HPLC. We have already employed this method in our previous study focused on the determination of the absolute configuration of butylone [31], thus HPLC was selected as the method of choice in this study.…”

Section: Enantioseparationmentioning

confidence: 99%

“…In the continuation of our systematic study of NPS [27,31], we introduce a comparison of two NPS homologuesmethylone and pentylone-in an aqueous solution. Employing the methods of VCD, ECD, IR spectroscopy and ultraviolet (UV) absorption spectroscopy supported by the DFT calculations at B3LYP/6-311++G(d,p) or B3PW91/6 311++G(d,p) levels, including solvent effects, we elucidated in detail the 3D structure of both drugs and compared their structural features.…”

Section: Introductionmentioning

confidence: 99%

Methylone and pentylone: structural analysis of new psychoactive substances

et al. 2019

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Purpose The growing availability of new psychoactive substances with unknown toxicity is alarming all over the world. The simplicity of acquiring these drugs of abuse from internet markets has caused an increase in the total number of seizures. We present the first systematic spectroscopic study of methylone and pentylone, which are in the class of synthetic cathinones. Methods High performance liquid chromatography (HPLC) was used for the enantioseparation of methylone and pentylone. The substances were further analysed by the conventional methods of ultraviolet (UV) and infrared (IR) absorption and chiroptical methods, specifically electronic circular dichroism (ECD) and vibrational circular dichroism (VCD). The obtained data were supported with the density functional theory (DFT) calculations using the B3LYP or B3PW91 functional and 6-311++G(d,p) basis sets, including the solvent effects. Results The 3D structure of methylone and pentylone in solution was revealed. Moreover, the chiral separation of both studied substances was achieved and the absolute configuration of the respective enantiomers was determined. Conclusion Vibrational circular dichroism spectroscopy seems to be the best of the methods employed to distinguish structurally similar chiral substances, especially in combination with quantum chemical calculations. According to the structural analysis, 5 and 9 stable conformers of methylone and pentylone, respectively, were revealed in an aqueous solution. Finally, very good agreement between the experimental and simulated spectra was achieved.

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Structure of heroin in a solution revealed by chiroptical spectroscopy

et al. 2020

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In this work, the 3‐D structure of the well‐known opioid drug heroin in a solution was investigated. The goal was to provide a complete and detailed description of the stable conformers with their relative abundances. This knowledge is very important from the pharmaceutical and forensic point of view as it could help significantly with deeper understanding of heroin's metabolism and the development of antagonist medicines for the case of an overdose. As heroin is a chiral compound with five stereogenic centres, the methods of chiroptical spectroscopy supplemented by density functional theory (DFT) calculations were applied to study its conformations in chloroform solution. The selected chiroptical methods, namely, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD), are inherently sensitive to the 3‐D structure of small‐ to medium‐sized chiral organic molecules. A thorough conformational analysis revealed four stable conformers of heroin in chloroform solution, where the conductor‐like polarizable continuum model of the solvent was used for all the calculations. The simulated ultraviolet (UV), infrared (IR), ECD, and VCD spectra were compared with the experimental ones and very good agreement was found, which enabled a detailed structure description and interpretation of the spectra. Chiroptical spectroscopy in combination with DFT calculations proved to be a very sensitive tool for the analysis of the 3‐D structure of heroin in a solution in contrast with conventional spectroscopic methods. Especially, the application of VCD seems to be a promising approach for monitoring structural changes, for instance, those caused by solvents or interactions with other agents.

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Structure determination of butylone as a new psychoactive substance using chiroptical and vibrational spectroscopies

Cited by 19 publications

References 38 publications

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Methylone and pentylone: structural analysis of new psychoactive substances

Structure of heroin in a solution revealed by chiroptical spectroscopy

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