Methylmethaqualone

Methylmethaqualone (MMQ) is a quinazolinone and an analogue of methaqualone that has similar sedative and hypnotic properties to its parent compound (resulting from its agonist activity at the β subtype of the GABAA receptor), and is much more potent. Methylmethaqualone differs from methaqualone by 4-methylation on the phenyl ring. It was made illegal in Germany in 1999 and listed by the DEA as a "drug of forensic interest" at about the same time, but little other information is available. It would appear that this compound was sold on the black market in Germany as a designer drug analogue of methaqualone.[1][2]

Methylmethaqualone
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: Anlage I (Authorized scientific use only)
Identifiers
IUPAC name
  • 3-(2,4-dimethylphenyl)-2-methylquinazolin-4(3H)-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H16N2O
Molar mass264.322 g·mol−1
3D model (JSmol)
SMILES
  • O=C1c3c(\N=C(/N1c2ccc(cc2C)C)C)cccc3
InChI
  • InChI=1S/C17H16N2O/c1-11-8-9-16(12(2)10-11)19-13(3)18-15-7-5-4-6-14(15)17(19)20/h4-10H,1-3H3 Y
  • Key:MPMDMUROZIYIIM-UHFFFAOYSA-N Y
  (verify)

Animal studies of methylmethaqualone have shown it to produce convulsions at only slightly above the effective sedative dose,[3] and anecdotal reports from human users have confirmed that it can have a pro-convulsive effect, which has potential to make this compound particularly hazardous if taken in excessive doses.

References
  1. Klein RF, Hays PA (January–June 2003). "Detection and Analysis of Drugs of Forensic Interest, 1992 - 2001; A Literature Review" (PDF). Microgram Journal. DEA. 1 (1–2): 60. Archived from the original (PDF) on 2011-07-19.
  2. Angelos SA, Lankin DC, Meyers JA, Raney JK (March 1993). "The structural identification of a methyl analog of methaqualone via 2-dimensional NMR techniques". Journal of Forensic Sciences. 38 (2): 455–65. doi:10.1520/JFS13428J. PMID 8455002.
  3. Boltze KH, Dell HD, Lehwald H, Lorenz D, Rueberg-Schweer M (August 1963). "[Substituted 4-Quinazolinone Derivatives As Hypnotics and Anticonvulsants]". Arzneimittel-Forschung (in German). 13: 688–701. PMID 14085923.
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