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Urine Mescaline Screening with a Biochip Array Immunoassay and Quantification by Gas Chromatography–Mass Spectrometry

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Urine Mescaline Screening with a Biochip Array Immunoassay and Quantification by Gas Chromatography–Mass Spectrometry ORIGINAL ARTICLE Urine Mescaline Screening With a Biochip Array Immunoassay and Quantification by Gas Chromatography–Mass Spectrometry Dilek Battal, PhD,* Allan J. Barnes, BSc,† Marisol S. Castaneto, MS,† Thomas M. Martin, PhD,‡ Kevin L. Klette, PhD,‡ and Marilyn A. Huestis, PhD† INTRODUCTION Abstract: Mescaline, the primary psychoactive chemical in peyote Naturally occurring plant-based psychoactive drugs cactus, has been consumed for thousands of years in ancient recently gained popularity because of wide distribution over religious ceremonies. The US military wanted to determine if the Internet.1 In 2012, the United Nations Office on Drugs and mescaline intake was a problem for personnel readiness. Twenty Crime (UNODC) evaluated the emergence of new psychoac- thousand seventeen urine specimens negative for cannabinoids, tive substances (NPS) by surveying 240 respondents from 80 cocaine, opiates, and amphetamines were tested for mescaline with countries and territories.2 Eighty-three percent reported NPS the Randox Drugs of Abuse V (DOA-V) biochip array immunoassay appearance in their drug markets with over 20 substances at the manufacturer’s recommended cutoff of 6 mcg/L. A sensitive fi fi fi identi ed from plant-based origins, including mescaline. and speci c method for mescaline quanti cation in urine was devel- Mescaline (3,4,5-trimethoxyphenylethylamine), the primary oped and fully validated. Extracted analytes were derivatized with peyote cactus (Lophophora williamsii) hallucinogen, contains pentafluoropropionic anhydride and pentafluoropropanol and quan- fi – button-shaped seeds that are soaked in water to prepare a tea ti ed by gas chromatography mass spectrometry (GC/MS) with or dried and chewed to produce psychedelic effects.3 Ancient electron impact ionization. Standard curves, using linear least 2 Toltec and Aztec Indians included peyote in their religious squares regression with 1/x weighting, were linear from 1 to 250 4 fi . ceremonies and to relieve hunger, fatigue, and treat diseases. mcg/L with coef cients of determination 0.994. Intra- and inter- The Native American Church continues to preserve peyote assay imprecision was ,4.4 coefficient of variation (%CV), with rituals, and despite efforts to ban the peyote, federal courts accuracies .90.4%. Mean extraction efficiencies were .92.0% exempted sacramental use of peyote from criminal penalties.5 across the linear range. This fully validated method was applied Mescaline, a naturally occurring alkaloid, also can be for the confirmation of urinary mescaline in 526 presumptive- produced synthetically. It was first isolated in 1897 by Heffter positive specimens and 198 randomly selected presumptive- and synthesized in 1919 by Späth.6,7 Mescaline’s chemical negative specimens at the manufacturer’s 6 mcg/L cutoff. No structure was the lead compound for hundreds of homologs, specimen confirmed positive at the GC/MS limit of quantification analogs, and related derivatives.8 Peyote and mescaline are of 1 mcg/L. Results indicated that during this time frame, there was listed as Schedule I hallucinogens under the Controlled Sub- insufficient mescaline drug use in the military to warrant routine stances Act in the United States.9 screening in the drug testing program. However, mescaline stability, Mescaline is a serotonin receptor agonist, with affinity although assessed, could have contributed to lower prevalence. We for 5-HT1A and 5-HT2A/B/C receptors.10–12 The proportion also present a validated GC/MS method for mescaline quantification of mescaline agonism on each receptor subtype is less clear, in urine for reliable confirmation of suspected mescaline intake. as is the action on dopaminergic and noradrenergic sys- Key Words: mescaline, peyote, GC/MS, herbal drugs, urine tems.11–14 Because of its low lipid solubility and polar molecular characteristics, mescaline does not easily pass (Ther Drug Monit 2015;37:805–811) the blood–brain barrier, and therefore, higher (180– 360 mg) doses are needed to produce psychotropic effects.13,14 Mescaline is rapidly absorbed, with onset of Received for publication March 7, 2015; accepted April 29, 2015. effects between 30 minutes and 2 hours after ingestion, last- From the *Department of Toxicology, Faculty of Pharmacy, Mersin University, ing 10–12 hours. In humans, 87% of an oral dose is excreted Turkey; †Chemistry and Drug Metabolism, Intramural Research Program, within 24 hours and 92% within 48 hours,15 with a plasma National Institute on Drug Abuse, National Institutes of Health, Baltimore, half-life of 6 hours.10,13,15–19 Maryland; and ‡Drug Testing and Program Policy, Office of the Secretary of Defense, Operational Readiness and Safety, Washington, District of Clinical effects of mescaline, similar to the psychedelic Columbia. action of lysergic acid diethylamide (LSD) and 3,4- The authors declare no conflict of interest. methylenedioxymethamphetamine (MDMA), include eupho- Correspondence: Marilyn A. Huestis, PhD, Chemistry and Drug Metabolism, ria, hallucinations, depersonalization, and psychoses.16,20–22 In IRP, National Institute on Drug Abuse, Biomedical Research Center, rodent models, mescaline modulates locomotion, exploration, National Institutes of Health, 251 Bayview Boulevard, Suite 200 Room 19,23–25 19,26,27 05A-721, Baltimore, MD 21224 (e-mail: [email protected]). cognitive function, aggression, and startle and – Copyright © 2015 Wolters Kluwer Health, Inc. All rights reserved. motor responses.28 30 Mescaline is reported to undergo Ther Drug Monit Volume 37, Number 6, December 2015 805 Copyright © 2015 Wolters Kluwer Health, Inc. Unauthorized reproduction of this article is prohibited. Battal et al Ther Drug Monit Volume 37, Number 6, December 2015 O-demethylation, N-acetylation, and amine oxidation31,32; Chemicals and Reagents however, all metabolites are believed to be inactive.18 Mescaline and deuterated mescaline (mescaline-d9) There are multiple published analytical methods for internal standard (IS) were purchased from Cerilliant Corpo- mescaline quantification in plasma,33,34 urine,35 hair,36 and ration (Round Rock, TX). Pentafluoropropionic anhydride postmortem tissues,37 or as part of a sympathomimetic amine (PFPA) and pentafluoropropanol (PFPOH) were obtained from screening assay.38 It is critical for military readiness for their Thermo Scientific (Waltham, MA). Clean Screen ZSDAU020 drug testing laboratories to identify new drugs of abuse (syn- (10 mL per 200 mg) extraction columns were acquired from thetic cannabinoids, cathinones) or other compounds entering United Chemical Technologies (Bristol, PA). Organic solvents or re-entering the illicit drug market. The mission of the US were high-performance liquid chromatography grade. Potas- military Drug Demand Reduction Program (DDRP) is to deter sium phosphate monobasic, potassium phosphate dibasic, and illicit and prescription drug abuse through education, out- acetic acid were from JT Baker (Phillipsburg, NJ), and reach, and awareness programs to ensure fitness for duty. ammonium hydroxide, methylene chloride, 2-propanol (IPA), The primary aims of this research were to screen 20,000 methanol, ethyl acetate, and acetonitrile were purchased from US military urine specimens by the Randox Drugs of Abuse Fisher Scientific (Fair Lawn, NJ). V (DOA-V) mescaline biochip array immunoassay and to quantify urine mescaline by gas chromatography–mass spec- Calibrators and Quality Control Samples trometry (GC/MS). Working mescaline standard solutions (100, 1000, and 10,000 mcg/L) were prepared by diluting 1.0 g/L stock MATERIALS AND METHODS solution with methanol. Working urine calibrators (1.0, 5.0, 10, 25, 50, 100, and 250 mcg/L) were prepared daily by Authentic Specimens fortifying appropriate amounts of working standard into 1.0 Urine specimens were screened and quantified for mL blank urine from drug-free volunteers. Quality control mescaline by GC/MS under an interagency agreement (QC) solutions were prepared in methanol from different lots between the Department of Defense (DoD) Drug Demand of stock solutions than calibrators. Low, medium, and high Reduction Initiative and the National Institutes on Drug QC samples across the dynamic range of the assay were Abuse, National Institutes of Health. We tested 20,017 prepared daily in drug-free urine at final concentrations of 3.0, anonymized DoD urine specimens previously screened 30, and 150 mcg/L. Deuterated stock IS (mescaline-d9) was negative for amphetamines, cannabinoids, cocaine, opiates, diluted with methanol to achieve a working IS concentration and phencyclidine. Per US military sample collection stan- of 500 mcg/L. Fifty-microliter working IS was added to each dard operating procedures, all urine specimens were stored at sample before extraction, yielding a final IS concentration of room temperature (RT) before initial analysis. These speci- 25 mcg/L. All standards, QCs, and IS solutions were stored in mens were collected from US service members stationed amber vials at 2208C. worldwide between July 2011 and June 2012. Extraction and Derivatization Procedure Randox DOA-V Biochip Array Technology Drug-free urine (1 mL) was pipetted into 10-mL Screening polypropylene tubes and fortified with appropriate amounts The Randox (Crumlin, Co, Antrim, United Kingdom) of calibrator or QC solutions and 50 mL working IS. One DOA-V biochip array technology allows simultaneous mul- hundred-microliter methanol was added to authentic speci- tiple competitive immunoassays. Drug in the specimen and mens to account for the volume of
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