Chemical profiling and classification of cannabis through electrospray ionization coupled to Fourier transform ion cyclotron resonance mass spectrometry and chemometrics

Borille, Bruna Tassi; Ortiz, Rafael S.; Mariotti, Kristiane de Cássia; Vanini, Gabriela; Tose, Lílian V.; Filgueiras, Paulo R.; Marcelo, Marcelo C. A.; Ferrão, Marco Flôres; Anzanello, Michel J.; Limberger, Renata Pereira; Romão, Wanderson

doi:10.1039/c7ay01294b

Cited by 21 publications

(18 citation statements)

References 42 publications

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“…7 The most abundant cannabinoids present in the Cannabis plant are: 9,10 (i) cannabidiol (CBD), an anticonvulsant drug tested in treatments of epileptic patients, 11 in addition to being anxiolytic, anti-inflammatory, antipsychotic, antispasmodic and analgesic; 12 (ii) cannabigerol (CBG), which has antiproliferative and antiglaucoma activities 13 as well as antibiotic, anti-inflammatory, antifungal and analgesic activities; 12 (iii) cannabinol (CBN), 1 a sedative and anticonvulsant that is anti-inflammatory; 12 (iv) cannabichromene (CBC), which is anti-inflammatory, antifungal and analgesic; 12 and (v) Δ 9 -tetrahydrocannabinol (Δ 9 -THC), the main psychoactive compound of the Cannabis plant. 1,[14][15][16][17][18] Most cannabinoids have a 21 carbon atom structural feature, with possible variations in the length of their side chains (C1-C5) attached to the aromatic ring. In the most common homologs, the n-pentyl side chain is replaced by n-propyl, and these analogues are named using the suffix "varin", for example, Δ 9 -tetrahydrocannabivarin (Δ 9 -THCV), cannabidivarin (CBDV) and cannabinovarin (CBNV).…”

Section: Introductionmentioning

confidence: 99%

“…16 Our group has explored the identification of constitutional isomers of cannabinoids that are found in Cannabis. 17,18 Figures 1a-1c illustrate some of these compounds as cannabinodiol (CBND), CBN and cannabifuran (CBF) with molecular formula (M) = C 21 H 26 O 2 , double bond equivalent (DBE) of 9 and an average molecular weight (M w ) of 310 Da ( Figure 1a); CBD, CBC, cannabicyclol (CBL), Δ 9 -trans-THC, Δ 9 -cis-THC and Δ 8 -trans-tetrahydrocannabinol (Δ 8 -THC), with M = C 21 H 30 O 2 , DBE 7, and an M w of 314 Da ( Figure 1b); and the cannabidiolic (CBDA), cannabinchromenic (CBCA), cannabicyclolic (CBLA), Δ 9 -tetrahydrocannabinolic A and B (Δ 9 -THCA A and B, respectively) and Δ 8 -tetrahydrocannabinolic (Δ 8 -THCA) acids, M = C 22 H 30 O 4 , DBE 8, and M w = 358 Da (Figure 1c).…”

Section: Introductionmentioning

confidence: 99%

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Analysis of Isomeric Cannabinoid Standards and Cannabis Products by UPLC‑ESI‑TWIM-MS: a Comparison with GC‑MS and GC × GC-QMS

Santos¹,

Tose²,

Silva³

et al. 2018

J. Braz. Chem. Soc.

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The Cannabis sativa L. plant has a complex chemical composition, containing various chemical compounds such as terpenes, sugars, hydrocarbons, steroids, flavonoids, and amino acids. Few works have attempted to identify the constitutional isomers of cannabinoids that are found in the plant. The present study reported the analysis of seven cannabinoid standards: five neutral and two acidic, as well as Cannabis products (hashish and marijuana) and parts of the Cannabis plant (flower and leaf) using mono-dimensional gas chromatography coupled with mass spectrometry (GC-MS) and two-dimensional gas chromatography coupled with quadrupole MS (GC × GC-QMS), ultra performance liquid chromatography coupled with electrospray ionization-quadrupole-time of flight (UPLC-ESI-QTOF)-MS and UPLC-ESI-travelling wave ion mobility (TWIM)-MS. The results of GC-MS demonstrated close retention times (∆t R = 1.303 min) in separation of the five cannabinoid standards, whereas GC × GC-QMS provided a substantially better identification and distinction of constitutional isomers of cannabinoids, where a total of 11 cannabinoids were identified in the hashish sample. UPLC-QTOF-MS and UPLC-TWIM-MS data obtained complete chemical information, in which ESI(+) revealed the presence of seven constitutional isomers of Δ 9-tetrahydrocannabinol (∆ 9-THC), whereas ESI(-) proved the presence of four isomers of Δ 9-tetrahydrocannabinolic acid A (Δ 9-THCA A).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Analysis of Isomeric Cannabinoid Standards and Cannabis Products by UPLC‑ESI‑TWIM-MS: a Comparison with GC‑MS and GC × GC-QMS

Santos¹,

Tose²,

Silva³

et al. 2018

J. Braz. Chem. Soc.

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“…In general, the sensitivity of FSI(−) in the detection of cannabinoids was higher than that of PSI(−), highlighting the ion detected at m/z 357 related to Δ 9 -tetrahydrocannabinolic acid (Δ 9 -THCA), or cannabidiol acid (CBDA) or their isomers, 47,48 identified with intensity of 1.29 × 10 9 from FSI(−) and 7.91 × 10 8 from PSI(−).…”

Section: F I G U R Ementioning

confidence: 98%

“…However, the signal at m/z 381 attributed to the chlorine adduct of cannabigerolic acid (CBGA) or cannabitriol (CBT), or their isomers, 47,48 was detected with an intensity more than three times higher using PSI(−). In addition, 8β,11-diOH-Δ 9 -THC, a Cannabis metabolite used as a blood marker for drug consumption screening, 49 was identified with better sensitivity by PSI(−) than by FSI(−).…”

Section: F I G U R Ementioning

confidence: 99%

Fiber spray ionization mass spectrometry in forensic chemistry: A screening of drugs of abuse and direct determination of cocaine in urine

Filho

Santos

Borges

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Ambient mass spectrometry techniques are much required in forensic chemistry to evaluate evidence with low analytical interference, high confidence, and accuracy. However, traditional methodologies, such as paper spray ionization, have been shown to present low sensitivity in the analysis of illicit drugs from biological matrices. Methods Fiber spray ionization mass spectrometry (FSI‐MS) was developed using a capillary polypropylene (PP) hollow fiber. Seized samples of drugs, i.e. a tablet, blotter paper, hashish, and cocaine powder, were analyzed. Cocaine was quantified from whole urine by dipping the fiber directly into solution. FSI‐MS was tested for the analysis of a sample of urine obtained from a drug abuse suspect. Results The FSI(+) analysis showed the detection of different types of synthetic drugs in tablet and blotter paper samples, e.g. amphetamine, cathinones, phenethylamines, and opioids, while pure cocaine and different types of coca alkaloids were identified from cocaine powder with good sensitivity and high mass accuracy. The hashish analysis by FSI(−) revealed signals of cannabinoids, cannabinoid acids, and cannabinoid derivatives, detected mainly as [M − H]− ions or chlorine adducts [M + Cl]−. The quantification of cocaine in whole urine showed good sensitivity and precision with limits of detection and quantification of 5.16 and 17.21 ng/mL, respectively, linearity above 0.999, and relative standard deviation below 2.71%. The evaluation of seized sample of urine showed the detection of cocaine with relative ion intensity greater than 36%, as well as the metabolites benzoylecgonine and cocaethylene with a relative intensity of 1.4% and 6%, respectively. Conclusions The developed FSI‐MS method has the potential to be applied to forensic sample evaluation as well as to determine illicit drugs from biological matrices in toxicological analysis. The use of a capillary PP fiber has advantages as an extractor agent and ionizing substrate, and also the feature of it being dipped directly into the sample, thus preserving the integrity of the sample, which makes this a very promising ambient mass spectrometry method and relevant to forensic chemistry.

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“…It has often been applied for the prompt screening analysis of different polar analytes, including natural or modified illicit drugs, and allows a fast, detailed, and reliable fingerprinting of complex forensic samples. [44][45][46][47] In this way, this work will show and discuss the use of FT-ICR MS All mass spectra were externally calibrated previously by using an arginine solution (0.05 mg ml −1 ).…”

Section: F I G U R E 1 Structures Of Psychoactive Drugs Commonly Markmentioning

confidence: 99%

Exploring the chemical profile of designer drugs by ESI(+) and PSI(+) mass spectrometry—An approach on the fragmentation mechanisms and chemometric analysis

et al. 2020

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The consumption of design drugs, frequently known as new psychoactive substances (NPS), has increased considerably worldwide, becoming a severe issue for the responsible governmental agencies. These illicit substances can be defined as synthetic compounds produced in clandestine laboratories in order to act as analogs of schedule drugs mimetizing its chemical structure and improving its pharmacological effects while hampering the control and making regulation more complicated. In this way, the development of new methodologies for chemical analysis of NPS drugs is indispensable to determine a novel class of drugs arising from the underground market. Therefore, this work shows the use of high-resolution mass spectrometry Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) applying different ionization sources such as paper spray ionization (PSI) and electrospray ionization (ESI) in the evaluation of miscellaneous of seized drugs samples as blotter paper (n = 79) and tablet (n = 100). Also, an elucidative analysis was performed by ESI(+) MS/MS experiments, and fragmentation mechanisms were proposed to confirm the chemical structure of compounds identified. Besides, the results of ESI(+) and PSI(+)-FT-ICR MS were compared with those of GC-MS, revealing that ESI(+)MS showed greater detection efficiency among the methodologies employed in this study. Moreover, this study stands out as a guide for the chemical analysis of NPS drugs, highlighting the differences between the techniques of ESI(+)-FT-ICR MS, PSI(+)-FT-ICR MS, and GC-MS.

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Chemical profiling and classification of cannabis through electrospray ionization coupled to Fourier transform ion cyclotron resonance mass spectrometry and chemometrics

Abstract: The chemical profile of cannabinoids obtained from 68 samples of cannabis seeds is determined by ESI-FT-ICR MS as function of different growth periods.

Cited by 21 publications

References 42 publications

Analysis of Isomeric Cannabinoid Standards and Cannabis Products by UPLC‑ESI‑TWIM-MS: a Comparison with GC‑MS and GC × GC-QMS

Analysis of Isomeric Cannabinoid Standards and Cannabis Products by UPLC‑ESI‑TWIM-MS: a Comparison with GC‑MS and GC × GC-QMS

Fiber spray ionization mass spectrometry in forensic chemistry: A screening of drugs of abuse and direct determination of cocaine in urine

Exploring the chemical profile of designer drugs by ESI(+) and PSI(+) mass spectrometry—An approach on the fragmentation mechanisms and chemometric analysis

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