Molecularly imprinted polymer for selective determination of Δ9-tetrahydrocannabinol and 11-nor-Δ9-tetrahydrocannabinol carboxylic acid using LC-MS/MS in urine and oral fluid

Abstract

The use of molecularly imprinted polymers (MIPs) for solid phase extraction (MISPE) allows a rapid and selective extraction compared with traditional methods. Determination of Δ(9)-tetrahydrocannabinol (THC) and 11-nor-Δ(9)-tetrahydrocannabinol carboxylic acid (THC-COOH) in oral fluid (OF) and urine was performed using homemade MISPEs for sample clean-up and liquid chromatography tandem mass spectrometry (LC-MS/MS). Cylindrical MISPE shaped pills were synthesized using catechin as a mimic template. MISPEs were added to 0.5 mL OF or urine sample and sonicated 30 min for adsorption of analytes. For desorption, the MISPE was transfered to a clean tube, and sonicated for 15 min with 2 mL acetone:acetonitrile (3:1, v/v). The elution solvent was evaporated and reconstituted in mobile phase. Chromatographic separation was performed using a SunFire C18 (2.5 μm; 2.1 × 20 mm) column, and formic acid 0.1% and acetonitrile as mobile phase, with a total run time of 5 min. The method was fully validated including selectivity (no endogenous or exogenous interferences), linearity (1-500 ng/mL in OF, and 2.5-500 ng/mL in urine), limit of detection (0.75 and 1 ng/mL in OF and urine, respectively), imprecision (%CV <12.3%), accuracy (98.2-107.0% of target), extraction recovery (15.9-53.5%), process efficiency (10.1-46.2%), and matrix effect (<-55%). Analytes were stable for 72 h in the autosampler. Dilution 1:10 was assured in OF, and Quantisal™ matrix effect showed ion suppression (<-80.4%). The method was applied to the analysis of 20 OF and 11 urine specimens. This is the first method for determination of THC and THC-COOH in OF using MISPE technology.

Quantification and Evaluations of Catechin Hydrate Polymeric Nanoparticles Used in Brain Targeting for the Treatment of Epilepsy

“…Although, most of these research studies reported simultaneous development with other catechins at the same time, that is, no reports of plasma analysis are available for catechin individually. Only one method was reported in urine sample analysis for catechins by Lendoiro et al [44]. In addition, the most important reason for the proposed study is a lack of an available method for brain tissue as well as plasma analysis of catechin hydrate alone.…”

Fast confirmation for marijuana metabolite: THC-COOH, ultra-fast LC—MS/MS run time, and application to routine samples

“…Elution time was given as 6.34 min. Molecularly imprinted polymers were used in another study, where extraction time was more than 65 min [4]. In another study, Kwon et al [31] have developed and validated a liquid chromatography-electrospray ionization-tandem mass spectrometric method (LC-ESI-MS/MS) for the direct determination of THC-COOH and its glucuronide in urine.…”

“…Despite of the very low concentration of Δ 9 -THC in urine, the maximum psychologic effect lasts for 4-6 h. Δ 9 -THC metabolizes very quickly. Firstly, it is converted to its active metabolite 11-nor-Δ 9 -hydroxy-THC (11-OH-THC) through hydroxylation, and then, it is oxidized to form inactive 11-nor-Δ 9 -carboxy-THC (THC-COOH) which is conjugated with glucuronide, existing in both the free and glucuronide form and mainly excreted in urine [4]. Δ 9 -THC metabolites may be detected in urine for up to 12 days following a single oral dose.…”

Molecularly imprinted probe for solid‐phase extraction of hippuric and 4‐methylhippuric acids directly from human urine samples followed by MEKC analysis

“…These polymers are obtained by the chemical fixation of functional monomers around a template , resulting in cavities with binding sites, complementary to the template . MIPs have been efficiently used to extract drugs from different samples, like urine , plasma , water , beef liver extracts , soil and hair . Moreover, different SPE approaches have been developed with MIPs.…”