Methylmethaqualone

Summary

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 3 times as potent in animal models.[1] 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.[2][3]

Methylmethaqualone
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: Anlage I (Authorized scientific use only)
Identifiers
  • 3-(2,4-dimethylphenyl)-2-methylquinazolin-4(3H)-one
CAS Number
  • 3244-75-5 checkY
PubChem CID
  • 63382
ChemSpider
  • 57045 checkY
UNII
  • OBQ1BQR74T
CompTox Dashboard (EPA)
  • DTXSID00172675 Edit this at Wikidata
Chemical and physical data
FormulaC17H16N2O
Molar mass264.328 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C1c3c(\N=C(/N1c2ccc(cc2C)C)C)cccc3
  • 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)

Animal studies of methylmethaqualone have shown it to produce convulsions at only slightly above the effective sedative dose,[4] 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 edit

  1. ^ DE Patent 1124504B - Verfahren zur Herstellung von 2-Methyl-3-(2',4'-dimethylphenyl)-4-oxo-3,4-dihydrochinazolin
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.