Effects of lipophilicity and functional groups of synthetic cannabinoids on their blood concentrations and urinary excretion

作者: Hidenao Kakehashi , Noriaki Shima , Akari Ishikawa , Atsushi Nitta , Ryutaro Asai

DOI: 10.1016/J.FORSCIINT.2019.110106

关键词: Synthetic cannabinoidsValineUrineOctanolChemistryCarboxamideLipophilicityPartition coefficientChromatographyPharmacokinetics

摘要: The influence of lipophilicity and functional groups synthetic cannabinoids (SCs) on their blood concentrations urinary excretion has been studied by analyzing urine specimens sampled from drivers who were involved in a car crashes under the SCs. A total 58 (26 31 specimens), within 13h occurrence, analyzed liquid chromatography-tandem mass spectrometry. Fifteen SCs detected those specimens; categorized as follows: Class 1, Naphthoyl/Benzoyl indole (EAM2201 three other analogs); 2, Indole-3-carboxylate/carboxamide containing naphthol/quinol (5F-PB-22 four 3, Indazole-3-carboxamide valine/tert-leucine derivative (5F-AMB five analogs). calculated index log P, octanol/water participation coefficient, Classes 3 ranged between 5.01-8.14, 5.80-6.74 2.29-3.81, respectively. detectable 12 out 13 specimens, but 1 2 not urine. Our analytical results indicated that boundary line for detectability lies P 4 5. varied widely (0.0036-31ng/ml) depending while much smaller variation was observed among (0.10-5.0ng/ml).

参考文章(18)
Ragnar Thomsen, Line M Nielsen, Niels B Holm, Henrik B Rasmussen, Kristian Linnet, Indices Consortium, None, Synthetic cannabimimetic agents metabolized by carboxylesterases. Drug Testing and Analysis. ,vol. 7, pp. 565- 576 ,(2015) , 10.1002/DTA.1731
Noriaki Shima, Munehiro Katagi, Hiroe Kamata, Kei Zaitsu, Tooru Kamata, Akihiro Miki, Hitoshi Tsuchihashi, Tsutomu Sakuma, Nobuo Nemoto, Conjugates of p-hydroxymethamphetamine and 4-hydroxy-3-methoxymethamphetamine in blood obtained from methamphetamine and 3,4-methylenedioxymethamphetamine users: analysis by LC-MS-MS Forensic Toxicology. ,vol. 26, pp. 58- 65 ,(2008) , 10.1007/S11419-008-0054-X
Frank Musshoff, Burkhard Madea, Gerhard Kernbach-Wighton, Wolfgang Bicker, Stefan Kneisel, Melanie Hutter, Volker Auwärter, Driving under the influence of synthetic cannabinoids ("Spice"): a case series International Journal of Legal Medicine. ,vol. 128, pp. 59- 64 ,(2014) , 10.1007/S00414-013-0864-1
Olaf H. Drummer, Requirements for bioanalytical procedures in postmortem toxicology Analytical and Bioanalytical Chemistry. ,vol. 388, pp. 1495- 1503 ,(2007) , 10.1007/S00216-007-1238-7
Ariane Wohlfarth, Marisol S. Castaneto, Mingshe Zhu, Shaokun Pang, Karl B. Scheidweiler, Robert Kronstrand, Marilyn A. Huestis, Pentylindole/Pentylindazole Synthetic Cannabinoids and Their 5-Fluoro Analogs Produce Different Primary Metabolites: Metabolite Profiling for AB-PINACA and 5F-AB-PINACA. Aaps Journal. ,vol. 17, pp. 660- 677 ,(2015) , 10.1208/S12248-015-9721-0
Marisol S. Castaneto, David A. Gorelick, Nathalie A. Desrosiers, Rebecca L. Hartman, Sandrine Pirard, Marilyn A. Huestis, Synthetic cannabinoids: Epidemiology, pharmacodynamics, and clinical implications Drug and Alcohol Dependence. ,vol. 144, pp. 12- 41 ,(2014) , 10.1016/J.DRUGALCDEP.2014.08.005
Kathryn A. Seely, Jeff Lapoint, Jeffery H. Moran, Liana Fattore, Spice drugs are more than harmless herbal blends: a review of the pharmacology and toxicology of synthetic cannabinoids Progress in Neuro-psychopharmacology & Biological Psychiatry. ,vol. 39, pp. 234- 243 ,(2012) , 10.1016/J.PNPBP.2012.04.017
J. K. Yeakel, B. K. Logan, Blood Synthetic Cannabinoid Concentrations in Cases of Suspected Impaired Driving Journal of Analytical Toxicology. ,vol. 37, pp. 547- 551 ,(2013) , 10.1093/JAT/BKT065
C. Heather Ashton, Pharmacology and effects of cannabis: a brief review British Journal of Psychiatry. ,vol. 178, pp. 101- 106 ,(2001) , 10.1192/BJP.178.2.101
Xingxing Diao, Karl B. Scheidweiler, Ariane Wohlfarth, Shaokun Pang, Robert Kronstrand, Marilyn A. Huestis, In Vitro and In Vivo Human Metabolism of Synthetic Cannabinoids FDU-PB-22 and FUB-PB-22. Aaps Journal. ,vol. 18, pp. 455- 464 ,(2016) , 10.1208/S12248-016-9867-4