You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameMethaqualone
Accession NumberDB04833
TypeSmall Molecule
GroupsIllicit, Withdrawn
Description

Methaqualone is a sedative-hypnotic drug that is similar in effect to barbiturates, a general central nervous system depressant. The sedative-hypnotic activity was first noted by Indian researchers in the 1950s and in 1962 methaqualone itself was patented in the US by Wallace and Tiernan. Its use peaked in the early 1970s as a hypnotic, for the treatment of insomnia, and as a sedative and muscle relaxant. It has also been used illegally as a recreational drug, commonly known as Quaaludes, Sopors, Ludes or Mandrax (particularly in the 1970s in North America) depending on the manufacturer. Since at least 2001, it has been widely used in South Africa, where it is commonly referred to as “smarties” or “geluk-tablette” (meaning happy tablets). Clandestinely produced methaqualone is still seized by government agencies and police forces around the world. [Wikipedia]

Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
QuaaludeRorer
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number72-44-6
WeightAverage: 250.2952
Monoisotopic: 250.11061308
Chemical FormulaC16H14N2O
InChI KeyJEYCTXHKTXCGPB-UHFFFAOYSA-N
InChI
InChI=1S/C16H14N2O/c1-11-7-3-6-10-15(11)18-12(2)17-14-9-5-4-8-13(14)16(18)19/h3-10H,1-2H3
IUPAC Name
2-methyl-3-(2-methylphenyl)-3,4-dihydroquinazolin-4-one
SMILES
CC1=CC=CC=C1N1C(C)=NC2=CC=CC=C2C1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as quinazolines. These are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthyridines
Sub ClassQuinazolines
Direct ParentQuinazolines
Alternative Parents
Substituents
  • Quinazoline
  • Toluene
  • Pyrimidone
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of insomnia, and as a sedative and muscle relaxant.
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include delirium, convulsions, muscle spasms or seizure, cardiac arrest, shortness or loss of breath, vomiting or nausea, and coma or death. The LD50 for mice is 1250 mg/kg and for rats is 326 mg/kg (Strasenburg Labs).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9953
Blood Brain Barrier+0.9921
Caco-2 permeable+0.8171
P-glycoprotein substrateNon-substrate0.7737
P-glycoprotein inhibitor IInhibitor0.6427
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.8537
CYP450 2C9 substrateNon-substrate0.6892
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6475
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateInhibitor0.5
CYP450 2D6 substrateNon-inhibitor0.9593
CYP450 2C19 substrateNon-inhibitor0.8585
CYP450 3A4 substrateNon-inhibitor0.8509
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5384
Ames testAMES toxic0.5126
CarcinogenicityNon-carcinogens0.9142
BiodegradationNot ready biodegradable0.9488
Rat acute toxicity2.8349 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9864
hERG inhibition (predictor II)Non-inhibitor0.61
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point120 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0407 mg/mLALOGPS
logP2.54ALOGPS
logP3.17ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity77.11 m3·mol-1ChemAxon
Polarizability27.32 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Potential Analgesics. Part I. Synthesis of substituted 4-quinazolones, I. K. Kacker and S. H. Zaheer, J. Ind. Chem. Soc. 28 (1951), pp. 344–346.

General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Comments
comments powered by Disqus
Drug created on September 11, 2007 15:07 / Updated on September 16, 2013 17:25