25C-NBOMe - New potent hallucinogenic substance identified on the drug market

Institute of Forensic Research, Westerplatte 9, 31033 Krakow, Poland. Electronic address: .
Forensic science international (Impact Factor: 2.14). 09/2012; 227(1-3). DOI: 10.1016/j.forsciint.2012.08.027
Source: PubMed


This publication reports analytical properties of a new hallucinogenic substance identified in blotter papers seized from the drug market, namely 25C-NBOMe [2-(4-chloro-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine]. The identification was based on results of comprehensive study including several analytical methods, i.e., GC-EI-MS (without derivatization and after derivatization with TFAA), LC-ESI-QTOF-MS, FTIR and NMR. The GC-MS spectrum of 25C-NBOMe was similar to those obtained for other representatives of the 25-NBOMe series, with dominant ions observed at m/z=150, 121 and 91. Fragment ions analogic to those in 2C-C (4-chloro-2,5-dimethoxy-β-phenylethanamine) were also observed, but their intensities were low. Derivatization allowed the determination of molecular mass of the investigated substance. The exact molecular mass and chemical formula were confirmed by LC-QTOF-MS experiments and fragmentation pattern under electrospray ionization was determined. The MS/MS experiments confirmed that the investigated substance was N-(2-methoxy)benzyl derivative of 2C-C. The substance was also characterized by FTIR spectroscopy to corroborate its identity. Final elucidation of the structure was performed by NMR spectroscopy.

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    • "Several substances were from cases elaborated at the Institute of Forensic Research (IFR) and their analytical properties were verified by gas chromatography with electron impact mass spectrometry (GC-EI-MS), LC-QTOF-MS, Fourier transform infrared spectroscopy (FTIR), and nuclear magnetic resonance (NMR) according to the used in IFR procedures. [16] [17] [18] All solvents were HPLC grade. Methanol, acetonitrile, and formic acid 98–100% were purchased from Merck (Warszawa, Poland). "
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    ABSTRACT: In recent years, many new psychoactive substances (NPS) from several drug classes have appeared on the drug market. These substances, also known as 'legal highs', belong to different chemical classes. Despite the increasing number of NPS, there are few comprehensive screening methods for their detection in biological specimens. In this context, the purpose of this study was to develop a fast and simple liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening procedure for NPS in blood. The elaborated method allows the simultaneous screening of 143 compounds from different groups (number of compounds): cathinones (36), phenethylamines (26), tryptamines (18), piperazines (9), piperidines (2), synthetic cannabinoids (34), arylalkylamines (7), arylcyclohexylamines (3), aminoindanes (2), and other drugs (6). Blood samples (0.2 mL) were precipitated with acetonitrile (0.6 mL). The separation was achieved with gradient mobile phase of 0.1% formic acid in acetonitrile and 0.1% formic acid in water in 14 min. Detection of all compounds was based on multiple reaction monitoring (MRM) transitions. The total number of transitions monitored in dynamic mode was 432. The whole procedure was rapid and simple. The limits of detection (LODs) estimated for 104 compounds were in the range 0.01-3.09 ng/mL. The extraction recoveries determined for 32 compounds were from 1.8 to 133%. The procedure was successfully applied to the analysis of forensic blood samples in routine casework. The developed method should have wide applicability for rapid screening of new drugs of abuse in forensic or clinical samples. The procedure can be easily expanded for more substances. Copyright © 2015 John Wiley & Sons, Ltd. Copyright © 2015 John Wiley & Sons, Ltd.
    No preview · Article · May 2015 · Drug Testing and Analysis
    • "psychedelic drug 2C-C (4-chloro-2,5-dimethoxy-phenylethyl- amine) by substituting a hydrogen at the amine nitrogen with a 2-methoxybenzyl (BOMe) group. Alternative abbreviations used for 25C-NBOMe include 2C-C-NBOMe, NBOMe-2C-C and Cimbi-82 [19]. 25C-NBOMe acts as a potent partial agonist of 5-HT 2A (serotonin) receptors [15]. "
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    ABSTRACT: This paper reports on a fatal overdose case involving the potent hallucinogenic drug 25C-NBOMe (2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine). In the present case, a young male was hospitalized after the recreational use of this potent drug. He died at the hospital at approximately 12h after ingestion, with preceding signs of serotonin toxicity. Medico-legal autopsy was performed on the deceased, during which time peripheral whole blood, urine, vitreous humor, liver and gastric content samples were submitted for toxicological examination. Further, whole blood collected at the hospital at 2-4h following ingestion of the drug was analyzed. 25C-NBOMe and a demethylated and glucuronidated metabolite of 25C-NBOMe were identified in the urine and blood samples using ultra-performance liquid chromatography with high-resolution time-of-flight mass spectrometry (UPLC-HRTOF-MS). Subsequently, 25C-NBOMe was quantified in the peripheral whole blood (0.60μg/kg), urine (2.93μg/kg), vitreous humor (0.33μg/kg), liver (0.82μg/kg) and gastric content (0.32μg total) samples collected during autopsy and in the ante-mortem whole blood (0.81μg/kg) by ultra-performance liquid chromatography with tandem mass spectrometry (UPLC-MS/MS). The autopsy findings were consistent with acute poisoning. Based on the toxicological findings, the cause of death was determined to be a fatal overdose of 25C-NBOMe in combination with amphetamine intake. To our knowledge, the present paper reports the first quantification of 25C-NBOMe in biological specimens from a fatal intoxication case. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.
    No preview · Article · Mar 2015 · Forensic science international
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    • "However, compared to previous 2C compounds, NBOMes have a significantly higher affinity at the 5-HT2A receptor (Halberstadt & Geyer 2014). As a consequence, sublingual doses as low as 100 µg may produce threshold effects (Zuba, Sekuła & Buczek 2013). Drug effects are likely to be similar to the 2C hallucinogens and LSD, including powerful visual and sensory effects, alterations in cognition and affect, and mystical experiences (Erowid & Erowid 2013). "
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    ABSTRACT: Abstract A new class of synthetic hallucinogens called NBOMe has emerged, and reports of adverse effects are beginning to appear. We report on a case of a suicide attempt after LSD ingestion which was analytically determined to be 25I-NBOMe instead. Clinicians need to have a high index of suspicion for possible NBOMe ingestion in patients reporting the recent use of LSD or other hallucinogens.
    Full-text · Article · Nov 2014 · Journal of psychoactive drugs
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