Abstract
Purpose
The information on analytical methods for 4-quinazolinone recreational drugs, such as methaqualone, etaqualone and 2-methoxyqualone, is almost scant. In this study, product ion spectra of gas chromatography−tandem mass spectrometry (GC−MS/MS) with different collision energies were presented for these drugs. Because 2-methoxyqualone is a new recreational drug discovered in dubious tablets very recently, much more detailed data obtained by different types of mass spectrometry instruments, and quantification data of 2-methoxyqualone in the tablet together with its validation were demonstrated.
Methods
The methods for analyses were GC−MS/MS, high-resolution ultra-high-performance liquid chromatography–quadrupole time-of-flight mass spectrometry and liquid chromatography−tandem mass spectrometry.
Results
The GC−MS/MS product ion spectra of the three compounds with different collision energies have not been reported before. They were very useful to tentatively identify unknown compounds. If a reference standard is available, the final identification and quantification can be achieved by measurements of product ion spectra and in selected reaction monitoring mode very easily by GC−MS/MS. The final identification and quantification for the new 2-methoxyqualone were performed in this way. The content of the compound was 69.8 ± 0.5% (w/w) in the tablet. Acetaminophen and caffeine coexisted in the tablet with approximate concentrations at 10 and 5%, respectively.
Conclusions
In this article, we have presented product ion spectra of methaqualone, etaqualone and 2-methoxyqualone at different collision energies by GC−MS/MS for the first time. In addition, this is the first paper to describe the details of quantification of 2-methoxyqualone in the authentic seized product.
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References
Psychonaut wiki (2022) Methaqualone. https://psychonautwiki.org/wiki/Methaqualone#Legal_status. Accessed 9 Mar 2022
Hammer H, Bader BM, Ernert C, Bundgaard C, Bunch L, Hoestgaard-Jensen K, Schroeder OH-U, Bastlund JF, Gramowski-Voß A, Jensen AA (2015) A Multifaceted GABAA receptor modulator: functional properties and mechanism of action of the sedative-hypnotic and recreational drug methaqualone (Quaalude). Mol Pharmacol 88:401–420. https://doi.org/10.1124/mol.115.099291
Pascarelli EF (1973) Methaqualone abuse, the quiet epidemic. JAMA 224:1512–1514. https://doi.org/10.1001/jama.1973.03220250034011
González ER (1981) Methaqualone abuse implicated in injuries, deaths nationwide. JAMA 246:813–819. https://doi.org/10.1001/jama.1981.03320080003001
Wetli CV (1983) Changing patterns of methaqualone abuse: a survey of 246 fatalities. JAMA 249:621–626. https://doi.org/10.1001/jama.1983.03330290043027
Yang H, Liu J, Dai L, Wang Y, Wei J, Wurita A (2021) Detection and quantification of psychotropic drug etaqualone in human hair using GC–MS/MS. Leg Med 53:101964. https://doi.org/10.1016/j.legalmed.2021.101964
Wikipedia (2020) Etaqualone. https://en.wikipedia.org/wiki/Etaqualone. Accessed 9 Mar 2022
Yang H, Wang S, Qi H, Liu J, Wang Y, Gu J, Wurita A, Hasegawa K (2022) 2-Methoxyqualone, a new recreational drug, discovered from a package seized by the police: a preliminary report. Forensic Toxicol. https://doi.org/10.1007/s11419-022-00626-w
Peters FT, Drummer OH, Musshoff F (2007) Validation of new methods. Forensic Sci Int 165:216–224. https://doi.org/10.1016/j.forsciint.2006.05.021
Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K (2014) Postmortem distribution of α-pyrrolidinobutiophenone in body fluids and solid tissues of a human cadaver. Leg Med 16:241–246. https://doi.org/10.1016/j.legalmed.2014.05.001
Hasegawa K, Minakata K, Suzuki M, Suzuki O (2021) The standard addition method and its validation in forensic toxicology. Forensic Toxicol 39:311–333. https://doi.org/10.1007/s11419-021-00585-8 (open access article)
Woods KM (2021) Two fatalities involving mebroqualone. J Anal Toxicol 45:308–311. https://doi.org/10.1093/jat/bkaa077 (open access article)
Grové AA, Rohwer ER, Laurens JB, Vorster BC (2006) The analysis of illicitt methaqualone containing preparations by gas chromatography–mass spectrometry for forensic purposes. J Forensic Sci 51:376–380. https://doi.org/10.1111/j.1556-4029.2006.00053.x
Kuila DK, Muhkopadhyay B, Lahiri SC (2006) Identification and estimation of methaqualone in toffee samples using gas chromatography-mass spectrometry, Fourier transform infrared spectrometry, and high-performance thin-layer chromatography. Forensic Sci Commun. https://archives.fbi.gov/archives/about-us/lab/forensic-science-communications/fsc/oct2006/research/2006_10_research02.htm Accessed May 2022
Casale JF, Hays PA (2012) The characterization of etaqualone and differentiation from its 3- and 4-ethyl analogues. Microgram J 9:47–51 (open access article)
Wikipedia (2022) Methylmethaqualone. https://en.wikipedia.org/wiki/Methylmethaqualone. Accessed 19 Apr 2022
Ceschi A, Giardelli G, Müller DM, Elavumkudy S, Manini AF, Rauber-Lüthy C, Hofer KE (2013) Acute neurotoxicity associated with recreational use of methylmethaqualone confirmed by liquid chromatography tandem mass spectrometry. Clin Toxicol 51:54–57. https://doi.org/10.3109/15563650.2012.758855
Romanek K, Fels H, Dame T, Skopp G, Musshoff F, Eiglmeier H, Eyer F (2021) Return of the Quaaludes? Prolonged agitated delirium after intentional ingestion of the methaqualone analog SL-164 – a case report. Subst Abus 42:503–505. https://doi.org/10.1080/08897077.2021.1903648
Lund K, Srihari P, Suhandynata RT, Schwartz K, Fitzgerald RL, Kreshak AA (2022) Qua-alluding to the past: a case of methaqualone analog ingestion. J Anal Toxicol 46:e82–e87. https://doi.org/10.1093/jat/bkab103
Wikipedia (2022) SL-164. https://en.wikipedia.org/wiki/SL-164. Accessed 17 Apr 2022
Ghit A, Assal D, Al-Shami AS, Hussein DEE (2021) GABAA receptors: Structure, function, pharmacology, and related disorders. J Genet Eng Biotechnol 19:123. https://doi.org/10.1186/s43141-021-00224-0 (open access article)
Falco M (1976) Methaqualone misuse: foreign experience and United States drug control policy. Int J Addict 11:597–610. https://doi.org/10.3109/10826087609056173
Acknowledgements
This study was supported in part by the National Natural Science Foundation of China (Grant No. 81860331).
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This article does not contain any studies with human participants or animals performed by any of the authors. The drug analyses were requested by the judicial authorities of the Inner Mongolia Hohhot City in China.
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Yang, H., Wang, Y., Liu, J. et al. The next addiction-causing drug class 4-quinazolinone derivatives: analyses of methaqualone analogs including recently discovered 2-methoxyqualone by different modes of mass spectrometry. Forensic Toxicol 41, 59–70 (2023). https://doi.org/10.1007/s11419-022-00631-z
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DOI: https://doi.org/10.1007/s11419-022-00631-z