5960. Methaqualone

Nomenclature

CAS number: 72-44-6
2-Methyl-3-(2-methylphenyl)-4(3H)-quinazolinone; 2-methyl-3-o-tolyl-4(3H)-quinazolinone; 3,4-dihydro-2-methyl-4-oxo-3-o-tolylquinazoline; metolquizolone; QZ-2; CI-705; R-148; TR-495; Parest; Quaalude; Somnafac.
C16H14N2O; mol wt 250.30.
C 76.78%, H 5.64%, N 11.19%, O 6.39%.

Description and references

Quinazoline sedative-hypnotic. Prepn: Kacker, Zaheer, J. Indian Chem. Soc. 28, 344 (1951); Klosa, J. Prakt. Chem. 14, 84 (1961); 20, 283 (1963). Review of syntheses: E. F. van Zyl, Forensic Sci. Int. 122, 142-149 (2001). GC determn in serum: M. A. Evenson, G. L. Lensmeyer, Clin. Chem. 20, 249 (1974). Metabolism: W. G. Stillwell et al., Drug Metab. Dispos. 3, 287 (1975). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Reports of abuse potential: D. S. Inaba et al., J. Am. Med. Assoc. 224, 1505 (1973); E. M. Pascarelli, ibid. 1512. Review of pharmacology: S. S. Brown, S. Goenechea, Clin. Pharmacol. Ther. 14, 314-324 (1973). Comprehensive description: D. M. Patel et al., Anal. Profiles Drug Subs. 4, 245-267 (1975). Comparison of abuse potential with benzodiazepines: M. H. Orzack et al., Int. J. Addict. 23, 449-467 (1988).

Chemical structure

Properties

Crystals, mp 120°; also given as mp 114-116°. uv max (ethanol): 225, 263, 304, 316 nm; (0.01N HCl): about 234, 269 nm. Sol in ethanol, ether, chloroform. Practically insol in water. LD50 orally in rats: 255 mg/kg (Goldenthal).

Derivative

Hydrochloride.

Nomenclature

CAS number: 340-56-7
C16H14N2O.HCl; mol wt 286.76.
C 67.01%, H 5.27%, N 9.77%, O 5.58%, Cl 12.36%.

Properties

Crystals, mp 255-265°. Sol in ether, ethanol. Practically insol in water.

Note

This is a controlled substance (depressant): 21 CFR, 1308.11.