Methylmethaqualone

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 checkY
  • Key:MPMDMUROZIYIIM-UHFFFAOYSA-N checkY
  (verify)

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 around the same potency. 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]

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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