Nitromethaqualone

Nitromethaqualone[1] is an analogue of methaqualone that has similar sedative and hypnotic properties.[2] It is significantly more potent (10x) compared to the parent compound; the typical dose is approximately 25 mg.[3] However, the aromatic nitro group is metabolised to the corresponding aniline, which proved to be a mutagen.[3] As a consequence, nitromethaqualone was not developed further due to toxicity concerns.

Nitromethaqualone

Clinical data
ATC code	none
Identifiers
IUPAC name 2-methyl-3-(2-methoxy-4-nitrophenyl)-4(3H)-quinazolinone
CAS Number	340-52-3
PubChem CID	63339
ChemSpider	57006
UNII	7G855468ZM
CompTox Dashboard (EPA)	DTXSID80187601
Chemical and physical data
Formula	C16H13N3O4
Molar mass	311.29 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C1C2=CC=CC=C2N=C(N1C3=C(OC)C=C(N(=O)=O)C=C3)C

References

1. US patent 3162634, Klosa J (Berlin, Germany), "2-Methyl-3-(2'-methyl-3'-chlorphenyl)-quinazolone-(4)", issued 1964-12-22
2. Szirmai A (November 1963). "[Pharmacological and Therapeutic Studies with a New Quinazolone Derivative, Nitromethaqualone]". Therapeutische Umschau. Revue Therapeutique (in German). 20: 542–6. PMID 14101319.
3. Van Boven M, Daenens P (October 1982). "Biotransformation and excretion of nitromethaqualone in rats and humans". Journal of Pharmaceutical Sciences. 71 (10): 1152–7. doi:10.1002/jps.2600711019. PMID 7143214.