List of methaqualone analogues

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Methaqualone analogues are a group of 4-quinazolinone derivatives typified by the sedative and hypnotic drug methaqualone. Methaqualone itself was invented in the 1950s as an alternative to the older barbiturate class of sedatives. It has sedative/hypnotic and muscle relaxant effects and was sold mainly as a sleeping pill, but also as an anxiolytic. Methaqualone was widely prescribed during the 1960s and 1970s but was removed from sale following issues with substance abuse and addiction. While it did have some safety advantages over barbiturates in terms of its acute potential for lethal overdose, methaqualone became known for its tendency to produce euphoria and aphrodisiac effects, and is also highly disinhibiting, with a large proportion of methaqualone associated fatalities due to traffic accidents following driving under the influence of methaqualone, or comparable fatal accidents. [1] Unlike most sedative/hypnotic drugs, methaqualone and its relatives can also produce a paradoxical lowering of the seizure threshold, which causes complications with treatment of overdose because most anticonvulsant medications are also sedatives and so can be dangerous to combine with other sedative/hypnotic drugs. It is also powerfully synergistic with alcohol and is much more dangerous when mixed with alcohol than when consumed by itself. Following the withdrawal of methaqualone from legitimate sale in the early 1980s, it fell out of use in most of the world, but has continued to be a widely used illicit drug in South Africa following its investigation as an incapacitating agent by the apartheid-era chemical weapons program Project Coast, which resulted in large quantities of surplus methaqualone being sold on the black market to finance covert operations, and its subsequent popularity led to continuing clandestine manufacture. [2] Methaqualone analogues reappeared as designer drugs in the late 1990s, with derivatives such as methylmethaqualone and etaqualone being sold particularly in Germany, and subsequently around the world, with additional derivatives continuing to appear. [3] [4] [5]

Contents

Table of Qualones

See also

References

  1. ↑ Wetli CV. Changing patterns of methaqualone abuse. A survey of 246 fatalities. JAMA. 1983 Feb 4;249(5):621-6. PMID   6848871
  2. ↑ van Zyl EF. A survey of reported synthesis of methaqualone and some positional and structural isomers. Forensic Sci Int. 2001 Nov 1;122(2-3):142-9. doi : 10.1016/s0379-0738(01)00484-4 PMID   11672968
  3. ↑ Inger JA, Mihan ER, Kolli JU, Lindsley CW, Bender AM. DARK Classics in Chemical Neuroscience: Methaqualone. ACS Chem Neurosci. 2023 Feb 1;14(3):340-350. doi : 10.1021/acschemneuro.2c00697 PMID   36651763
  4. ↑ Tusiewicz K, Zawadzki M, Szpot P. A Historical Drug or a Current Problem? Determination of Methaqualone and Its Analogs in Biological Material via UHPLC-QqQ-MS/MS. Proceedings. 2024; 102(1):28. doi : 10.3390/proceedings2024102028 {{doi}}: unflagged free DOI (link)
  5. ↑ Tusiewicz K, Wachełko O, Szpot P, Zawadzki M. From historical drugs to present perils: UHPLC-QqQ-MS/MS determination of methaqualone and its designer analogs (NPS) with comprehensive fragmentation pathways study (QTOF). Toxicol Mech Methods. 2025 Mar;35(3):318-328. doi : 10.1080/15376516.2024.2426582 PMID   39508427
  6. ↑ Kuropka P, Zawadzki M, Szpot P. Emerging trends in methaqualone and analogues abuse: insights from online forums. Forensic Toxicol. 2023 Jul;41(2):329-331. doi : 10.1007/s11419-023-00665-x PMID   37169943
  7. ↑ Gujral ML, Saxena PN, Khauna BK. Potentiating effect of chlorpromazine hydrochloride on hypnosis induced by phenobarbitone and 2-ethyl-3-o-tolyl-4 (3H)-quinazolone. J. Indian med. Prof. 1956; 3:1098-9.
  8. ↑ Yang H, Wang Y, Liu J, Qiu S, Gu J, Bai H, Li J, Wurita A, Hasegawa K. 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. 2023 Jan;41(1):59-70. doi : 10.1007/s11419-022-00631-z PMID   36652055
  9. ↑ Ochiai T, Ishida R, Nurimoto S, Inoue I, Kowa Y. Pharmacology of a new hypnotic drug: HQ-355. Jpn J Pharmacol. 1972 Jun;22(3):431-4. doi : 10.1254/jjp.22.431 PMID   4539402
  10. ↑ Wang PF, Jensen AA, Bunch L. From Methaqualone and Beyond: Structure-Activity Relationship of 6-, 7-, and 8-Substituted 2,3-Diphenyl-quinazolin-4(3H)-ones and in Silico Prediction of Putative Binding Modes of Quinazolin-4(3H)-ones as Positive Allosteric Modulators of GABAA Receptors. ACS Chem Neurosci. 2020 Dec 16;11(24):4362-4375. doi : 10.1021/acschemneuro.0c00600 PMID   33170625
  11. ↑ Madjroh N, Olander ER, Bundgaard C, Söderhielm PC, Jensen AA. Functional properties and mechanism of action of PPTQ, an allosteric agonist and low nanomolar positive allosteric modulator at GABAA receptors. Biochem Pharmacol. 2018 Jan;147:153-169. doi : 10.1016/j.bcp.2017.11.006 PMID   29155148
  12. ↑ 450. Мефенаквалон (Mephenaqualone) Раздел I.A. Вещества с подтвержденной структурой
  13. ↑ 2-(2-chloro-4-methylphenyl)quinazoline-4(3h)-ketone compound and medical use thereof. Patent WO 2020/239050
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