scholarly journals Detection Times of Carboxylic Acid Metabolites of the Synthetic Cannabinoids JWH-018 and JWH-073 in Human Urine

2015 ◽  
Vol 39 (4) ◽  
pp. 280-286 ◽  
Author(s):  
S. Hegstad ◽  
A. A. Westin ◽  
O. Spigset
Keyword(s):  
Carboxylic Acid ◽  
Human Urine ◽  
Synthetic Cannabinoids ◽  
Acid Metabolites

scholarly journals Human Hepatocyte Metabolism of Novel Synthetic Cannabinoids MN-18 and Its 5-Fluoro Analog 5F-MN-18

2017 ◽  
Vol 63 (11) ◽  
pp. 1753-1763 ◽  
Author(s):  
Xingxing Diao ◽  
Jeremy Carlier ◽  
Mingshe Zhu ◽  
Marilyn A Huestis
Keyword(s):  
Carboxylic Acid ◽  
High Resolution ◽  
High Resolution Mass Spectrometry ◽  
Synthetic Cannabinoids ◽  
Human Hepatocytes ◽  
Binding Affinities ◽  
High Resolution Mass ◽  
Full Scan ◽  
Resolution Mass

Abstract BACKGROUND In 2014, 2 novel synthetic cannabinoids, MN-18 and its 5-fluoro analog, 5F-MN-18, were first identified in an ongoing survey of novel psychoactive substances in Japan. In vitro pharmacological assays revealed that MN-18 and 5F-MN-18 displayed high binding affinities to human CB1 and CB2 receptors, with Ki being 1.65–3.86 nmol/L. MN-18 and 5F-MN-18 were scheduled in Japan and some other countries in 2014. Despite increasing prevalence, no human metabolism data are currently available, making it challenging for forensic laboratories to confirm intake of MN-18 or 5F-MN-18. METHODS We incubated 10 μmol/L of MN-18 and 5F-MN-18 in human hepatocytes for 3 h and analyzed the samples on a TripleTOF 5600+ high-resolution mass spectrometer to identify appropriate marker metabolites. Data were acquired via full scan and information-dependent acquisition-triggered product ion scans with mass defect filter. RESULTS In total, 13 MN-18 metabolites were detected, with the top 3 abundant metabolites being 1-pentyl-1H-indazole-3-carboxylic acid, pentyl-carbonylated MN-18, and naphthalene-hydroxylated MN-18. For 5F-MN-18, 20 metabolites were observed, with the top 3 abundant metabolites being 5′-OH-MN-18, MN-18 pentanoic acid, and 1-(5-fluoropentyl)-1H-indazole-3-carboxylic acid. CONCLUSIONS We have characterized MN-18 and 5F-MN-18 metabolism with human hepatocytes and high-resolution mass spectrometry, and we recommend characteristic major metabolites for clinical and forensic laboratories to identify MN-18 and 5F-MN-18 intake and link observed adverse events to these novel synthetic cannabinoids.

scholarly journals Identification and Determination of 1,3-Thiazinane-4-carboxylic Acid in Human Urine—Chromatographic Studies

2022 ◽  
Vol 23 (2) ◽  
pp. 598
Author(s):  
Justyna Piechocka ◽  
Natalia Litwicka ◽  
Rafał Głowacki
Keyword(s):  
Carboxylic Acid ◽  
Human Urine ◽  
Clinical Analysis ◽  
Gas Chromatography Mass Spectrometry ◽  
Aqueous Environment ◽  
Limit Of Quantification ◽  
Isobutyl Chloroformate ◽  
United States Food ◽  
States Food

It is well established that homocysteine (Hcy) and its thiolactone (HTL) are reactive towards aldehydes in an aqueous environment, forming substituted thiazinane carboxylic acids. This report provides evidence that Hcy/HTL and formaldehyde (FA) adduct, namely 1,3-thiazinane-4-carboxylic acid (TCA) is formed in vivo in humans. In order to provide definitive proof, a gas chromatography–mass spectrometry (GC–MS) based method was elaborated to identify and quantify TCA in human urine. The GC–MS assay involves chemical derivatization with isobutyl chloroformate (IBCF) in the presence of pyridine as a catalyst, followed by an ethyl acetate extraction of the obtained isobutyl derivative of TCA (TCA-IBCF). The validity of the method has been demonstrated based upon United States Food and Drug Administration recommendations. The assay linearity was observed within a 1–50 µmol L−1 range for TCA in urine, while the lowest concentration on the calibration curve was recognized as the limit of quantification (LOQ). Importantly, the method was successfully applied to urine samples delivered by apparently healthy volunteers (n = 15). The GC–MS assay may provide a new analytical tool for routine clinical analysis of the role of TCA in living systems in the near future.

Identification of Tetrahydro-β-carboline-3-carboxylic Acid in Foodstuffs, Human Urine and Human Milk

1991 ◽  
Vol 121 (5) ◽  
pp. 646-652 ◽  
Author(s):  
Junko Adachi ◽  
Yasuhiko Mizoi ◽  
Takeaki Naito ◽  
Yumi Ogawa ◽  
Yoshiyuki Uetani ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Human Milk ◽  
Human Urine

scholarly journals Electrochemical analysis of the carboxy-14C-labelled aliphatic carboxylic acid metabolites resulting from tracer studies

1977 ◽  
Vol 167 (2) ◽  
pp. 505-507 ◽  
Author(s):  
G H Walker ◽  
D E Hathway
Keyword(s):  
Carboxylic Acid ◽  
Electrochemical Analysis ◽  
Acid Biosynthesis ◽  
Tracer Studies ◽  
Aliphatic Carboxylic Acid ◽  
Carboxylic Acid Groups ◽  
Acid Metabolites ◽  
Kolbe Reaction ◽  
Aliphatic Carboxylic Acids ◽  
Important Evidence

14C02 output from carboxy-14C-labelled aliphatic carboxylic acids is measured in the micro-scale Kolbe reaction. Irrespective of whether rats were dosed with 1,1-dichloro[1-14C]ethylene or with chloro[1-14C]acetic acid, 1 mol.equiv. of the resulting thio[14C]diglycollic acid yields by electrolysis approx. 0.7 equiv. of 14CO2, which is interpreted in terms of the labelling of one of the carboxylic acid groups of thiodiglycollic acid. This observation provides important evidence concerning thiodiglycollic acid biosynthesis from 1.1-dichloroethylene.

New polar acid metabolites in human urine

1981 ◽  
Vol 226 (2) ◽  
pp. 301-314 ◽  
Author(s):  
Albrecht Grupe ◽  
Gerhard Spiteller
Keyword(s):  
Human Urine ◽  
Acid Metabolites

LC–MS/MS method for the quantitation of metabolites of eight commonly-used synthetic cannabinoids in human urine – An Australian perspective

2012 ◽  
Vol 897 ◽  
pp. 22-31 ◽  
Author(s):  
Andrew D. de Jager ◽  
Janet V. Warner ◽  
Michael Henman ◽  
Wendy Ferguson ◽  
Ashley Hall
Keyword(s):  
Human Urine ◽  
Synthetic Cannabinoids
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