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Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques
The samples of plant material suspected to contain new psychoactive substances are very often the subject of chemical-toxicological analyses. Gas chromatography-mass spectrometry (MS), liquid chromatography-quadrupole time-of-flight-MS, and liquid chromatography-tandem MS were applied with the aim to identify synthetic cannabinoid, methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate (MMB-CHMICA) without the analytical standard, which is very often the case when a new drug arrives. The structure of compound was also confirmed by one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy and conformational analysis. After identification, methanolic extract of plant material containing MMB-CHMICA was successfully used for developing a multiple reaction monitoring method on liquid chromatography-tandem MS instrument. The optimization procedure is shown in detail. The complete fragmentation pattern and also the optimization of the extraction procedur...e of MMB-CHMICA from plant material were shown. The obtained data are useful for forensic, toxicological, and clinical purposes.
Keywords:
high-resolution mass spectrometry / identification of NPS / MMB-CHMICA / MRM optimization / synthetic cannabinoids
TY - JOUR
AU - Lukić, Vera
AU - Micić, Ružica
AU - Arsić, Biljana
AU - Mitić, Milan
AU - Jovanović, Miloš
AU - Pavlović, Aleksandra
PY - 2021
UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4050
AB - The samples of plant material suspected to contain new psychoactive substances are very often the subject of chemical-toxicological analyses. Gas chromatography-mass spectrometry (MS), liquid chromatography-quadrupole time-of-flight-MS, and liquid chromatography-tandem MS were applied with the aim to identify synthetic cannabinoid, methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate (MMB-CHMICA) without the analytical standard, which is very often the case when a new drug arrives. The structure of compound was also confirmed by one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy and conformational analysis. After identification, methanolic extract of plant material containing MMB-CHMICA was successfully used for developing a multiple reaction monitoring method on liquid chromatography-tandem MS instrument. The optimization procedure is shown in detail. The complete fragmentation pattern and also the optimization of the extraction procedure of MMB-CHMICA from plant material were shown. The obtained data are useful for forensic, toxicological, and clinical purposes.
PB - De Gruyter Open Ltd
T2 - Open Chemistry
T1 - Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques
VL - 19
IS - 1
SP - 1259
EP - 1273
DO - 10.1515/chem-2021-0113
ER -
@article{
author = "Lukić, Vera and Micić, Ružica and Arsić, Biljana and Mitić, Milan and Jovanović, Miloš and Pavlović, Aleksandra",
year = "2021",
abstract = "The samples of plant material suspected to contain new psychoactive substances are very often the subject of chemical-toxicological analyses. Gas chromatography-mass spectrometry (MS), liquid chromatography-quadrupole time-of-flight-MS, and liquid chromatography-tandem MS were applied with the aim to identify synthetic cannabinoid, methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate (MMB-CHMICA) without the analytical standard, which is very often the case when a new drug arrives. The structure of compound was also confirmed by one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy and conformational analysis. After identification, methanolic extract of plant material containing MMB-CHMICA was successfully used for developing a multiple reaction monitoring method on liquid chromatography-tandem MS instrument. The optimization procedure is shown in detail. The complete fragmentation pattern and also the optimization of the extraction procedure of MMB-CHMICA from plant material were shown. The obtained data are useful for forensic, toxicological, and clinical purposes.",
publisher = "De Gruyter Open Ltd",
journal = "Open Chemistry",
title = "Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques",
volume = "19",
number = "1",
pages = "1259-1273",
doi = "10.1515/chem-2021-0113"
}
Lukić, V., Micić, R., Arsić, B., Mitić, M., Jovanović, M.,& Pavlović, A.. (2021). Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques. in Open Chemistry
De Gruyter Open Ltd., 19(1), 1259-1273.
https://doi.org/10.1515/chem-2021-0113
Lukić V, Micić R, Arsić B, Mitić M, Jovanović M, Pavlović A. Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques. in Open Chemistry. 2021;19(1):1259-1273.
doi:10.1515/chem-2021-0113 .
Lukić, Vera, Micić, Ružica, Arsić, Biljana, Mitić, Milan, Jovanović, Miloš, Pavlović, Aleksandra, "Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques" in Open Chemistry, 19, no. 1 (2021):1259-1273,
https://doi.org/10.1515/chem-2021-0113 . .
