Palmitic acid ester of tetrahydrocannabinol (THC) and palmitic acid diester of 11-hydroxy-THC - Unsuccessful search for additional THC metabolites in human body fluids and tissues.
11-Hydroxy-THC
Fatty acid conjugate
Mass spectrometry
Nuclear magnetic resonance spectroscopy
Palmitic acid ester
Tetrahydrocannabinol
Journal
Forensic science international
ISSN: 1872-6283
Titre abrégé: Forensic Sci Int
Pays: Ireland
ID NLM: 7902034
Informations de publication
Date de publication:
Jan 2019
Jan 2019
Historique:
received:
14
08
2018
revised:
10
11
2018
accepted:
12
11
2018
pubmed:
28
11
2018
medline:
5
3
2019
entrez:
28
11
2018
Statut:
ppublish
Résumé
Fatty acid conjugates of hydroxy-metabolites of tetrahydrocannabinol (THC) or cannabinol have already been reported as metabolites in rats. In the herein presented investigation, palmitic acid esters of THC and its primary metabolite 11-hydroxy-delta9-tetrahydrocannabinol (11-OH-THC) were synthesized using esterification with palmitic acid chloride. Structural elucidation of the products was conducted using nuclear magnetic resonance spectroscopy (NMR) and liquid chromatography coupled to quadrupole time of flight mass spectrometry (LC-QToF-MS). For the confirmation of a previous cannabis use, body fluids (femoral blood, heart blood, urine, bile) of 27 death cases (all with known cannabis use), including adipose tissue homogenates of six of these cases as well as eleven plasma samples (probably all with regular cannabis use, confirmed by a high 11-nor-9-carboxy-delta9-tetrahydrocannabinol (THC-COOH) concentration (except one sample, >200ng/mL), were tested for THC and its main metabolites 11-OH-THC and THC-COOH using gas chromatography coupled to mass spectrometry (GC-MS). These samples as well as further tissue homogenates of autopsy cases (liver, kidney, brain) were additionally tested for the presence of THC palmitic acid ester or 11-OH-THC palmitic acid diester by means of a liquid chromatographic triple quadrupole mass spectrometric (LC-QQQ-MS) method, in order to evaluate a possible presence of these conjugates in humans. In none of the analyzed samples (in total 196 specimens; plasma (N=11), femoral blood (N=23), heart blood (N=25), urine (N=23), bile (N=27), liver (N=27), kidney (N=27), brain (N=27), adipose tissue (N=6)), palmitic acid esters of THC or 11-OH-THC could be proven. Even if the existence of these esters in human samples cannot be ruled out definitely, suitability as cannabis consumption markers does not seem likely based on our findings.
Identifiants
pubmed: 30481665
pii: S0379-0738(18)30536-X
doi: 10.1016/j.forsciint.2018.11.005
pii:
doi:
Substances chimiques
Biomarkers
0
Esters
0
11-hydroxy-delta(9)-tetrahydrocannabinol
26108-40-7
Palmitic Acid
2V16EO95H1
Dronabinol
7J8897W37S
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
86-95Informations de copyright
Copyright © 2018 Elsevier B.V. All rights reserved.