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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Groupsillicit, withdrawn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
SaltsNot Available
Brand names
NameCompany
QuaaludeRorer
Brand mixturesNot Available
CategoriesNot Available
CAS number72-44-6
WeightAverage: 250.2952
Monoisotopic: 250.11061308
Chemical FormulaC16H14N2O
InChI KeyInChIKey=JEYCTXHKTXCGPB-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassNaphthyridines
SubclassQuinazolines
Direct parentQuinazolines
Alternative parentsToluenes; Pyrimidones; Polyamines
Substituentstoluene; pyrimidone; benzene; pyrimidine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
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
Property Value Probability
Human Intestinal Absorption + 0.9953
Blood Brain Barrier + 0.9921
Caco-2 permeable + 0.8171
P-glycoprotein substrate Non-substrate 0.7737
P-glycoprotein inhibitor I Inhibitor 0.6427
P-glycoprotein inhibitor II Inhibitor 0.5
Renal organic cation transporter Non-inhibitor 0.8537
CYP450 2C9 substrate Non-substrate 0.6892
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Substrate 0.6475
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Inhibitor 0.5
CYP450 2D6 substrate Non-inhibitor 0.9593
CYP450 2C19 substrate Non-inhibitor 0.8585
CYP450 3A4 substrate Non-inhibitor 0.8509
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5384
Ames test AMES toxic 0.5126
Carcinogenicity Non-carcinogens 0.9142
Biodegradation Not ready biodegradable 0.9488
Rat acute toxicity 2.8349 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9864
hERG inhibition (predictor II) Non-inhibitor 0.61
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point120 °CPhysProp
Predicted Properties
PropertyValueSource
water solubility4.07e-02 g/lALOGPS
logP2.54ALOGPS
logP3.17ChemAxon
logS-3.8ALOGPS
pKa (strongest basic)-1.2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area32.67ChemAxon
rotatable bond count0ChemAxon
refractivity77.11ChemAxon
polarizability27.32ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD00557
KEGG CompoundC07560
PubChem Compound6292
PubChem Substance46507178
ChemSpider6055
BindingDB50089081
Drug Product Database2243257
WikipediaMethaqualone
ATC CodesN05CM01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
Drug created on September 11, 2007 15:07 / Updated on September 16, 2013 17:25