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Methylmethaqualone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Methylmethaqualone
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 3-(2,4-dimethylphenyl)-2-methylquinazolin-4(3H)-one
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC17H16N2O
Molar mass264.328 g·mol−1
3D model (JSmol)
  • 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)

Methylmethaqualone (MMQ) is aquinazolinone and an analogue ofmethaqualone that has similarsedative andhypnotic properties to its parent compound (resulting from its agonist activity at the β subtype of theGABAA 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 theDEA 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 adesigner druganalogue of methaqualone.[2][3]

Animal studies of methylmethaqualone have shown it to produceconvulsions 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.1 (1–2). DEA: 60. Archived fromthe 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.
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