电子烟中的植物尼古丁和合成尼古丁:能否用核磁共振波谱进行区分?

IF 3.7 3区 医学 Q2 CHEMISTRY, MEDICINAL
Chemical Research in Toxicology Pub Date : 2024-12-16 Epub Date: 2024-11-15 DOI:10.1021/acs.chemrestox.4c00398
Yulia B Monakhova, Klaudia Adels, Bernd W K Diehl
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引用次数: 0

摘要

为了规避监管框架,许多生产商开始在电子烟产品中用合成尼古丁(无烟草尼古丁,TFN)替代植物尼古丁(烟草尼古丁,TDN)。由于 TFN 的对映体合成和纯化成本较高,因此需要开发一种能明确区分两种来源的分析方法。为了追溯尼古丁的来源,可以使用 (R)-(-)-1,1'- 联萘-2,2'- 二基磷酸氢盐(BNPPA)作为手性络合剂,通过 1H NMR 光谱推测其对映体的纯度。为此,即使使用少量电子液体样品(定量限为 8 毫克/毫升尼古丁),也对低场 (LF) NMR 条件进行了优化。发现所有调查产品都含有一种异构体(很可能是 (S)-(-)- 尼古丁)。一种天然丰度的直接 13C NMR 方法已通过验证,可用于区分使用不同来源尼古丁生产的电子烟中的 (S)-TDN 和 (S)-TFN。该方法基于计算尼古丁分子中 10 个 C 位的相对 13C 含量,精确度低于 1H NMR 方法,可替代昂贵的高场 NMR 方法来区分外消旋体混合物和单一光学异构体,而在适当提取样品后,只有高精度 13C NMR 才能用于区分电子烟中的 (S)-TDN 和 (S)-TFN。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Plant-Derived and Synthetic Nicotine in E-Cigarettes: Is Differentiation with NMR Spectroscopy Possible?

To circumvent regulatory frameworks, many producers start to substitute plant-derived nicotine (tobacco-derived nicotine, TDN) by synthetic nicotine (tobacco-free nicotine, TFN) in e-cigarette products. Due to the higher costs of enantiomeric synthesis and purification of TFN, there is a need to develop an analytical method that clearly distinguishes between the two sources. To trace nicotine's origin, its enantiomeric purity can be postulated by 1H NMR spectroscopy using (R)-(-)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (BNPPA) as a chiral complexing agent. Low-field (LF) NMR conditions were optimized for this purpose even using a small amount of e-liquid sample (limit of quantification 8 mg/mL nicotine). All investigated products were found to contain one isomer (most likely (S)-(-)-nicotine). A direct 13C NMR method at natural abundance has been validated to differentiate (S)-TDN and (S)-TFN in e-cigarettes produced using nicotine of different origin. The method is based on calculation of the relative 13C content of 10 C-positions of the nicotine molecule with intraday and interday precisions below <0.2%. The method was applied to 12 commercial e-cigarette products labeled as containing TDN and TFN. Principal component analysis (PCA) was applied to the relative peak areas to visualize the difference between studied products. The LF 1H NMR method is a good alternative to expensive high-field NMR to differentiate between a racemate mixture and single optical isomers, whereas only high-precision 13C NMR can be used to distinguish (S)-TDN and (S)-TFN in e-cigarettes after appropriate sample extraction.

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来源期刊
CiteScore
7.90
自引率
7.30%
发文量
215
审稿时长
3.5 months
期刊介绍: Chemical Research in Toxicology publishes Articles, Rapid Reports, Chemical Profiles, Reviews, Perspectives, Letters to the Editor, and ToxWatch on a wide range of topics in Toxicology that inform a chemical and molecular understanding and capacity to predict biological outcomes on the basis of structures and processes. The overarching goal of activities reported in the Journal are to provide knowledge and innovative approaches needed to promote intelligent solutions for human safety and ecosystem preservation. The journal emphasizes insight concerning mechanisms of toxicity over phenomenological observations. It upholds rigorous chemical, physical and mathematical standards for characterization and application of modern techniques.
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