Chemistry:Methylmethaqualone

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Short description: Chemical compound
Methylmethaqualone
Methylmethaqualone.svg
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: Anlage I (Authorized scientific use only)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC17H16N2O
Molar mass264.322 g·mol−1
3D model (JSmol)
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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]

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

  1. DE Patent 1124504B - Verfahren zur Herstellung von 2-Methyl-3-(2',4'-dimethylphenyl)-4-oxo-3,4-dihydrochinazolin
  2. "Detection and Analysis of Drugs of Forensic Interest, 1992 - 2001; A Literature Review.". Microgram Journal (DEA) 1 (1–2): 60. January–June 2003. https://www.justice.gov/dea/programs/forensicsci/microgram/journal_v1/2003_1-2.pdf. 
  3. "The structural identification of a methyl analog of methaqualone via 2-dimensional NMR techniques". Journal of Forensic Sciences 38 (2): 455–65. March 1993. doi:10.1520/JFS13428J. PMID 8455002. 
  4. "[Substituted 4-Quinazolinone Derivatives As Hypnotics and Anticonvulsants]" (in German). Arzneimittel-Forschung 13: 688–701. August 1963. PMID 14085923.