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Erschienen in: Forensic Toxicology 1/2023

23.09.2022 | Original Article

Evaluation of decarboxylation efficiency of Δ9-tetrahydrocannabinolic acid and cannabidiolic acid by UNODC method

verfasst von: Kenji Tsujikawa, Yuki Okada, Hiroki Segawa, Tadashi Yamamuro, Kenji Kuwayama, Tatsuyuki Kanamori, Yuko. T. Iwata

Erschienen in: Forensic Toxicology | Ausgabe 1/2023

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Abstract

Purpose

Decarboxylation of Δ9-tetrahydrocannabinolic acid (Δ9-THCA) to Δ9-tetrahydrocannabinol (Δ9-THC) by heating is a common method for determining total Δ9-THC. In the manual for cannabis identification and analysis, the United Nations Office on Drugs and Crime (UNODC) proposed decarboxylation conditions. Although the manual’s primary analytical target is Δ9-THC, some reports also quantified cannabidiol (CBD). The authors assessed the efficiency of decarboxylation of Δ9-THCA and cannabidiolic acid (CBDA), a carboxylated form of CBD, under four decarboxylation conditions, including the UNODC condition.

Methods

Δ9-THCA and CBDA were heated in 2-mL glass vials at 150 °C for 12 min after the following treatment: condition A involves the addition of ethanol without capping, condition B involves non addition of solvent without capping, condition C involves non addition of solvent with capping, and condition D (UNODC condition) involves the addition of 0.5 mg/mL tribenzylamine (TBA) in ethanol without capping. The residue after heating was dissolved in methanol and then analyzed by high-performance liquid chromatography.

Results

The production of Δ9-THC and CBD was low (≤ 10.1%) under conditions A and B. Under condition C, Δ9-THC production was increased (53.4%), but CBD production was hardly improved (11.7%). Under condition D, Δ9-THC and CBD production dramatically increased to 83.2 and 71.0%, respectively.

Conclusions

These findings indicated that TBA improved the production of Δ9-THC and CBD from their carboxylated forms; however, even in the presence of TBA, their production did not reach 100%. Forensic toxicologists should understand the effectiveness and limitations of decarboxylation under the UNODC condition.
Literatur
1.
Zurück zum Zitat Federal register, Establishment of a domestic hemp production program, the United States Government (publication date January 19, 2021). Federal register, Establishment of a domestic hemp production program, the United States Government (publication date January 19, 2021).
2.
Zurück zum Zitat Cannabis legislation in Europe, an Overview. European Monitoring Centre for Drugs and Drug Addicition, 2017, Publications Office of the European Union, Luxembourg. Cannabis legislation in Europe, an Overview. European Monitoring Centre for Drugs and Drug Addicition, 2017, Publications Office of the European Union, Luxembourg.
6.
Zurück zum Zitat Recommended methods for the identification and analysis of cannabis and cannabis products, United Nations Office on Drugs and Crime, Vienna, 2009. Recommended methods for the identification and analysis of cannabis and cannabis products, United Nations Office on Drugs and Crime, Vienna, 2009.
10.
Zurück zum Zitat Wang M, Wang YH, Avula B, Radwan MM, Wanas AS, van Antwerp J, Parcher JF, ElSohly MA, Khan IA (2016) Decarboxylation study of acidic cannabinoids: a novel approach using ultra-high-performance supercritical fluid chromatography/photodiode array-mass spectrometry. Cannabis Cannabinoid Res 1:262–271. https://​doi.​org/​10.​1089/​can.​2016.​0020 CrossRef Wang M, Wang YH, Avula B, Radwan MM, Wanas AS, van Antwerp J, Parcher JF, ElSohly MA, Khan IA (2016) Decarboxylation study of acidic cannabinoids: a novel approach using ultra-high-performance supercritical fluid chromatography/photodiode array-mass spectrometry. Cannabis Cannabinoid Res 1:262–271. https://​doi.​org/​10.​1089/​can.​2016.​0020 CrossRef
15.
Zurück zum Zitat Christmann LJ (1928) Tertiary amine antioxidants, US Patent US1825654A. Christmann LJ (1928) Tertiary amine antioxidants, US Patent US1825654A.
Metadaten
Titel
Evaluation of decarboxylation efficiency of Δ9-tetrahydrocannabinolic acid and cannabidiolic acid by UNODC method
verfasst von
Kenji Tsujikawa
Yuki Okada
Hiroki Segawa
Tadashi Yamamuro
Kenji Kuwayama
Tatsuyuki Kanamori
Yuko. T. Iwata
Publikationsdatum
23.09.2022
Verlag
Springer Nature Singapore
Erschienen in
Forensic Toxicology / Ausgabe 1/2023
Print ISSN: 1860-8965
Elektronische ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-022-00645-7

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