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  3. The Identification of Synthetic Impurities in a Vape Pen Containing Δ9-Tetrahydrocannabiphorol Using Gas Chromatography Coupled with Mass Spectrometry
 

The Identification of Synthetic Impurities in a Vape Pen Containing Δ9-Tetrahydrocannabiphorol Using Gas Chromatography Coupled with Mass Spectrometry

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BORIS DOI
10.48620/36404
Date of Publication
October 12, 2024
Publication Type
Article
Division/Institute

Institute of Forensic...

DCBP Gruppe Prof. Sch...

Author
Schirmer, Willi
Institute of Forensic Medicine, Forensic Chemistry and Toxicology
Schürch, Stefan
DCBP Gruppe Prof. Schürch
Weinmann, Wolfgang
Institute of Forensic Medicine, Forensic Chemistry and Toxicology
Institute of Forensic Medicine
Series
Psychoactives
ISSN or ISBN (if monograph)
2813-1851
Publisher
MDPI
Language
English
Publisher DOI
10.3390/psychoactives3040030
Description
Δ9-Tetrahydrocannabiphorol (Δ9-THCP, THCP) a psychoactive cannabinoid recently found in Cannabis sativa L., is widely used as a legal marijuana substitute. THCP is encountered in sprayed Cannabis, edibles, and vape liquids. The distributors of such products claim that the THCP in use originates from a natural source. The legal status of this substance varies from country to country. THCP and similar cannabinoids with a dibenzoyprane structure have been banned in Switzerland since October 2023. A vape liquid, which contains 90% THCP and 10% terpenes according to the distributor, was analyzed by gas chromatography coupled with mass spectrometry (GC-MS). Besides CBP, CBDP, Δ9-THCP and Δ8-THCP and some terpenes, other compounds were found which probably result from a synthetic procedure. This sample contained 5-heptylresorcinol, the heptyl homologue of olivetol, a common precursor for the synthesis of tetrahydrocannabinol (THC). Bisalkylated compounds (m/z 476) were found as a result of the reaction of one equivalent of 5-heptylresorcinol with two equivalents of (+)-p-mentha-1,8-dien-4-ol or another precursor. Similar bisalkylated compounds are known as undesired side products of the synthesis of THC. The sample contained unidentified isomers of Δ9-THCP, presumably abnormal cannabinoids (abn-Δ9-THCP; abn-Δ8-THCP) and iso-cannabinoids (iso-THCP). Chiral derivatization with Mosher acid chlorides revealed that the Δ9-THCP in the sample was enantiopure.
Handle
https://boris-portal.unibe.ch/handle/20.500.12422/125176
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psychoactives-03-00030.cleaned (1).pdftextAdobe PDF1.11 MBpublishedOpen
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