Extraction and isolation of cannabinoids from marijuana seizures and characterization by 1H NMR allied to chemometric tools

Leite, Júlia de A.; Oliveira, Marcos Vinicius Lacerda de; Conti, Rena M.; Borges, Warley de Souza; Rosa, Thalles Ramon; Filgueiras, Paulo R.; Lacerda, Valdemar; Romão, Wanderson; Neto, Álvaro Cunha

doi:10.1016/j.scijus.2018.06.005

Cited by 24 publications

(8 citation statements)

References 21 publications

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“…Δ 9 -THC, Δ 8 -THC, Δ 8 - iso -THC, and Δ 4(8) - iso -THC were fully characterized using NMR data, and the complete 1 H and 13 C NMR assignments (Table –) have been determined on the basis of 1D and 2D NMR spectra ( 1 H and 13 C NMR, correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), and heteronuclear multiple bond correlation (HMBC)). The data were compared with those available in the literature. , …”

Section: Resultsmentioning

confidence: 99%

Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization

et al. 2020

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The chemical reactivity of cannabidiol is based on its ability to undergo intramolecular cyclization driven by the addition of a phenolic group to one of its two double bonds. The main products of this cyclization are Δ9-THC (trans-Δ-9-tetrahydrocannabinol) and Δ8-THC (trans-Δ-8-tetrahydrocannabinol). These two cannabinoids are isomers, and the first one is a frequently investigated psychoactive compound and pharmaceutical agent. The isomers Δ8-iso-THC (trans-Δ-8-iso-tetrahydrocannabinol) and Δ4(8)-iso-THC (trans-Δ-4,8-iso-tetrahydrocannabinol) have been identified as additional products of intramolecular cyclization. The use of Lewis and protic acids in different solvents has been studied to investigate the possible modulation of the reactivity of CBD (cannabidiol). The complete NMR spectroscopic characterizations of the four isomers are reported. High-performance liquid chromatography analysis and 1H NMR spectra of the reaction mixture were used to assess the percentage ratio of the compounds formed.

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Section: Resultsmentioning

confidence: 99%

Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization

et al. 2020

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“…Nuclear magnetic resonance (NMR)‐based methods are also employed to analyze Cannabis components (de Leite et al, 2018). It is an outstanding technique which helps to elucidate the chemical structures of unknown constituents (Citti et al, 2020; Stefkov et al, 2022).…”

Section: Analytical Methods For Phytocannabinoid Determination In Her...mentioning

confidence: 99%

“…Currently, a variety of analytical and spectroscopic approaches for the identification and quantification of Cannabis products are used and still being developed. The most prominent techniques are gas chromatography (GC) and high‐performance liquid chromatography (HPLC), but other methodologies are being used as well (Barthlott et al, 2021; de Leite et al, 2018; Duchateau et al, 2020; Sanchez, Baltensperger, & Kurouski, 2020; United Nations Office on Drugs and Crime, 2020). Furthermore, in recent years, chemometric tools have been introduced for the data treatment of complex matrices such as Cannabis.…”

Section: Introductionmentioning

confidence: 99%

Analytical strategies for herbal Cannabis samples in forensic applications: A comprehensive review

Slosse

Durme

Eliaerts

et al. 2023

WIREs Forensic Science

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Cannabis sativa L. is undoubtedly the most used recreational drug worldwide because of its desired acute psychotropic effects, like relaxation, euphoria and altered perceptions. In addition, promising medical properties of Cannabis components have gained a lot of attention, resulting in a debate to permit recreational Cannabis use in several countries. In recent years, this controversial plant was increasingly studied and a large number of scientific papers were published. Herbal Cannabis consists of a variable and complex matrix, which makes it challenging to properly seize and prepare the sample for qualitative and quantitative analysis. Moreover, both the adoption of legal cut‐off values in different countries for the Δ9‐tetrahydrocannabinol (THC) content in seizures, and the emergence of cannabidiol (CBD) based products, containing generally small but variable amounts of THC, urged the need for sensitive and reliable analytical techniques to accurately identify and quantify the components of interest. This review presents detailed information on the procedure prior to analysis and covers chromatographic and spectroscopic methods developed for the analysis of cannabinoids in seizures for different forensic purposes, that is, identification/quantification, potency testing, drug‐ and fiber‐type differentiation, age estimation, yield determination and Cannabis profiling. Advantages and drawbacks of existing methods, within a specific forensic context, are discussed. The application of chemometrics, which offers a powerful tool in interpreting complex data, is also explained. This article is categorized under: Toxicology > Cannabis Toxicology > Drug Analysis Forensic Chemistry and Trace Evidence > Presentation and Evaluation of Forensic Science Output

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“…Then in the high dose (2 mg) :0.28 × ? = 0.06 × 1000 ml = 214 ml for one mouse ( de A. Leite et al, 2018 ).…”

Section: Methodsmentioning

confidence: 99%

Anxiety, depression-like behaviors and biochemistry disorders induced by cannabis extract in female mice

Mohammed

Khardali

Oraiby

et al. 2021

Saudi Journal of Biological Sciences

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Cannabis is an annual herbaceous plant sometimes grown for decoration and used as bird food that looks like flax. The study wanted to determine if a Cannabis extract may have an effect on how anxious and depressed the female mice behaved. forty healthy female mice were divided into four groups. Tap water was administered to the first group (control). Ethanol was administered to second group (positive control). The third and four groups were given 1 and 2 mg/kg cannabis extract respectively. Treatment continued for 14 days. After therapy, the light–dark chamber, forced swimming, tail suspension, plus lamb and open field tests were done to assess anxiety and depressive behavior. The results indicated that the anxiety and depression were increased in treated females significantly compared to control. Biochemical results showed that DA,5-HT, AChE, GSH, GST, CAT and SOD were decreased while TBARS, corticosterone and cortisol were increased. In conclusion, cannabis effects this kind of females’ behavior but the mechanisms are not clear yet. We need more researches on this trend.

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Extraction and isolation of cannabinoids from marijuana seizures and characterization by 1H NMR allied to chemometric tools

Cited by 24 publications

References 21 publications

Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization

Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization

Analytical strategies for herbal Cannabis samples in forensic applications: A comprehensive review

Anxiety, depression-like behaviors and biochemistry disorders induced by cannabis extract in female mice

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