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Therefore, we investigated the metabolic profile of these compounds in human hepatocytes, an in vivo mouse model and authentic human urine samples from forensic cases. Mice were administered 1. Human urine samples were analyzed similarly. In vitro and in vivo results matched well. All methoxy groups could be demethylated; hydroxylation preferably occurred at the NBOMe ring. Phase I metabolites were extensively conjugated in human urine with glucuronic acid and sulfate. These data will help clinical and forensic laboratories to develop analytical methods and to interpret results. Substances Benzylamines Dimethoxyphenylethylamine Hallucinogens Phenethylamines 2- 4-iodo-2,5-dimethoxyphenyl -N- 2-methoxybenzyl ethanamine 2- 4-chloro-2,5-dimethoxyphenyl -N- 2-methoxyphenyl methyl ethanamine.

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Neurotoxicological profile of the hallucinogenic compound 25I-NBOMe

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Neurotoxicological profile of the hallucinogenic compound 25I-NBOMe

Federal government websites often end in. The site is secure. In recent years, N -methoxybenzyl-methoxyphenylethylamine NBOMe derivatives, a class of designer hallucinogenic drugs, have become popular drugs of abuse. These drugs have been the cause of severe intoxications and even deaths. They act as 5-HT 2A receptors agonists and have been reported to produce serotonin-like syndrome with bizarre behavior, severe agitation and seizures persisting for as long as 3 days. Like many low dose hallucinogenic drugs these compounds are often sold on blotter paper. Three different types of commercially available blotter papers reported to contain NBOMe derivatives were obtained. These blotter papers were screened using Direct Analysis in Real Time AccuTOF TM mass spectrometry followed by confirmation and quantification by high-performance liquid chromatography triple quadrapole mass spectrometry. Stimulation of 5-HT 2A receptors is responsible for the hallucinogenic effects of recreational drugs such as lysergic acid diethylamide LSD and 1- 2,5-dimethoxyiodophenyl aminopropane 2. These reports reveal NBOMe intoxicated patients are typically young males, 14—29 years old with clinical presentations of a serotonin-like syndrome with bizarre behavior and severe agitation and seizures persisting for as long as 3 days. Quantified distribution of 25I-NBOMe in body fluids and tissues from a case of traumatic death has also been reported We present the analysis of three different types of commercial available blotter papers reported to contain NBOMe derivatives. Upon opening the package, a Christmas music CD case was found that contained three different small bags containing blotter paper Figure 1. A set of the three different blotter paper products were each added to 10 mL of methanol which was then gently mixed to extract the NBOMe derivatives. Tokyo, Japan. The Direct Analysis in Real Time ion source had the helium gas flow rate at 2. The resolving power of the mass spectrometer was 6, full width at half maximum. The measured mass range was from 40 to 1, Da. In brief, a mass spectrum of PEG with average molecular weight was obtained with each data acquisition set as a reference standard to enable exact mass measurements. The PEG and methanol standards containing the NBOMe derivatives were measured by dipping the closed end of a cleaned glass melting point tube into the standard. The first analysis did not involve any sample preparation. The second analysis was performed by adding each blotter paper to 10 mL of methanol and gently mixing for 1 h. The methanol solutions were then sampled by dipping the closed end of a clean glass melting point tube into the methanol containing the blotter paper. The standards and samples were then moved back in forth, or wanded, in to the DART gas stream. Each of the samples or standards was wanded two times. The signal with the greatest abundance was used for the data analysis. The evaluation of the NBOMe derivatives in methanol was conducted over five separate days. They were analyzed ten times using different aliquots. The intra- and interday precision for the mass accuracy was calculated from the analysis of five aliquots of each NBOMe derivative standard on three separate days for a total of 15 replicates. Selectivity was determined if the individual NBOMe derivatives could be distinguished in with the mixture. The following gradient was used: 0. The acquisition mode used was multiple reaction monitoring. The total run time for the analytical method was 13 min. Stock standards were also evaluated for stability by allowing aliquots of the stock standards to sit at room temperature for 6 h. The absolute areas of aliquots of NBOMe derivatives kept at room temperature for 6 h were compared with the freshly prepared stock standards. These voltages produced greater abundance of product ions. All of the NBOMe derivatives present were distinguishable even though several of the NBOMe derivatives produced product ions with the same structure and theoretical mass. At the 60 and 90 V settings, the expected product ions were detected. This figure is available in black and white in print and in color at JAT online. The linear regression correlation coefficients r 2 for all the NBOMe calibration curves yielded the least fit mean r 2 of 0. The blotter paper was held with a pair of forceps and placed directly into the DART-MS gas stream and yielded spectra information in a few seconds. Previously published analyses of blotter papers containing NBOMe derivatives have not reported concentrations or accuracy of the vendor-advertised concentrations. The blotter papers were correctly labeled as to their major NBOMe derivative. The discrepancy in the calculated concentration versus the advertised concentrations of Felix the Cat blotter paper indicates that the advertised concentration may not be accurate and, in some cases, the concentration of the NBOMe derivative may be several times greater than expected. Both methods used were able to detect and differentiate between multiple NBOMe derivatives on the same blotter paper. As a library, NLM provides access to scientific literature. J Anal Toxicol. Published online Sep Justin L. Poklis , 1 Stephen A. Raso , 2 Kylie N. Alford , 2 Alphonse Poklis , 1, 2, 3 and Michelle R. Stephen A. Kylie N. Michelle R. Email: ude. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals. Abstract In recent years, N -methoxybenzyl-methoxyphenylethylamine NBOMe derivatives, a class of designer hallucinogenic drugs, have become popular drugs of abuse. Open in a separate window. Figure 1. Figure 2. Figure 3. Conflict of interest None declared. Acknowledgements The authors thank Dr Robert Cody for his helpful suggestions to improve this manuscript. References 1. Dean B. Journal of Medical Toxicology , 9 , Neuron , 53 , — Shulgin A. Psychopharmacol Commun , 1 , 93— Transform Press, Berkeley, CA. Heim R. Archiv der Pharmazie — Pharmaceutical and Medicinal Chemistry , , Pertz H. Entwicklung eines neuen struktur-wirkungskonzepts. Free University of Berlin, Berlin. Stellpflug S. Journal of Medical Toxicology , 10 , 45— Zuba D. Drug Testing and Analysis , 8 , — Forensic Science International , , 7— Rapid Communications in Mass Spectrometry , 18 , — Kelly A. Clinical Toxicology Philadelphia , 50 , Rose S. Clinical Toxicology Philadelphia , 50 , — Rose R. Clinical Toxicology Philadelphia , 51 , — Hill S. Suzuki J. Journal of Psychoactive Drugs , 46 , — Poklis J. Drug Testing and Analysis , 6 , — Tang M. Clinical Toxicology Philadelphia , 52 , — Laskowski L. Journal of Medical Toxicology , 11 , — Johnson R. Journal of Analytical Toxicology , 38 , — Grautoff S. Medizinische Klinik — Intensivmedizin und Notfallmedizin , , — Walterscheid J. Forensic Science International , , 14— Drug Enforcement Administration. Department of Justice Schedules of controlled substances: temporary placement of three synthetic phenethylamines into Schedule, I. Final order. Department of Justice. Federal Register , 78 , — Forrester M. Journal of Addictive Diseases , 33 , — Nikolaou P. Toxicological and legislative aspects. Drug and Chemical Toxicology , 38 , — Lawn W. Journal of Psychopharmacology , 28 , — Psychosomatics , 56 , — Steiner R. Journal of Forensic Science , 54 , — Journal of Analytical Toxicology , 35 , — Copy Download.

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