CAS： 340-52-3
MF： C16H13N3O4
Nitromethaqualone is a synthetic analogue of methaqualone, known for its potent sedative and hypnotic effects. It is significantly stronger than methaqualone, with a typical dose around 25 mg, making it approximately 10 times more potent than the parent compound. Despite its effectiveness, nitromethaqualone was not further developed due to safety concerns, particularly its potential mutagenic properties. The aromatic nitro group in nitromethaqualone is metabolized into an aniline derivative, which has been identified as a mutagen, raising significant health risks.
InChI:InChI=1/C16H13N3O4/c1-10-17-13-6-4-3-5-12(13)16(20)18(10)14-8-7-11(19(21)22)9-15(14)23-2/h3-9H,1-2H3
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The metabolic disposition of 14C-labeled nitromethaqualone was investigated in rats. Unlabeled nitromethaqualone was used for studies on humans. Nitromethaqualone was eliminated from the body after most of it had undergone biotransformation. Both humans and rats reduced the nitro group of nitromethaqualone to the corresponding amino derivative, which was partially transformed to the corresponding acety- lated form.
Nitromethaqualone [2-methyl-3(2′-methoxy-4′-nitrophenyl)-4(3H)-quinazolinone] and its three positional isomers formed by moving the nitro group on the phenyl ring containing the 2′-methoxyl group have been synthesized and characterized. It is shown that infrared spectroscopy, nuclear magnetic resonance spectroscopy, and electron impact mass spectroscopy combined with gas-liquid chromatography are capable of differentiating nitromethaqualone from any of the studied isomers, methaqualone, and mecloqualone.
