NAV

Methaqualone

Identification

Generic Name
Methaqualone
DrugBank Accession Number
DB04833
Background

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, sedative, and muscle relaxant commonly used for insomnia. 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.

Type
Small Molecule
Groups
Illicit, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 250.2952
Monoisotopic: 250.11061308
Chemical Formula
C16H14N2O
Synonyms
  • metacualona
  • Methaqualone
External IDs
  • CI-705
  • CN 38703
  • R-148
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Pharmacology

Indication

For the treatment of insomnia, and as a sedative and muscle relaxant.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms 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).

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Methaqualone is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Methaqualone can be increased when it is combined with Abametapir.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Methaqualone.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Methaqualone.
AgomelatineThe risk or severity of CNS depression can be increased when Methaqualone is combined with Agomelatine.
Food Interactions
Not Available

Products

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International/Other Brands
Quaalude (Rorer)

Categories

ATC Codes
N05CX02 — Methaqualone, combinationsN05CM01 — Methaqualone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Benzodiazines
Direct Parent
Quinazolines
Alternative Parents
Toluenes / Pyrimidones / Heteroaromatic compounds / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinazolines (CHEBI:6821)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7ZKH8MQW6T
CAS number
72-44-6
InChI Key
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

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 References
Not Available
Human Metabolome Database
HMDB0240285
KEGG Drug
D00557
KEGG Compound
C07560
PubChem Compound
6292
PubChem Substance
46507178
ChemSpider
6055
BindingDB
50089081
RxNav
6823
ChEBI
6821
ChEMBL
CHEMBL282052
ZINC
ZINC000002568176
Wikipedia
Methaqualone

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)120 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0407 mg/mLALOGPS
logP2.54ALOGPS
logP3.17Chemaxon
logS-3.8ALOGPS
pKa (Strongest Basic)1.18Chemaxon
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 RuleNoChemaxon
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 inhibitorInhibitor0.5
CYP450 2D6 inhibitorNon-inhibitor0.9593
CYP450 2C19 inhibitorNon-inhibitor0.8585
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0f79-8490000000-13cbb7614902871f6c7d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-85d9ca7a4db612e57f53
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-7338441bc527d8a21fea
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-186813867f0a7c9cbf49
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-0ee2ed3809d5e6c089b3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01c4-2920000000-ddf8384749f3b7847db8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9410000000-9d3535e153997994d411
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-165.3931391
predicted
DarkChem Lite v0.1.0
[M-H]-165.5252391
predicted
DarkChem Lite v0.1.0
[M-H]-148.06432
predicted
DeepCCS 1.0 (2019)
[M+H]+165.8677391
predicted
DarkChem Lite v0.1.0
[M+H]+165.8225391
predicted
DarkChem Lite v0.1.0
[M+H]+150.43983
predicted
DeepCCS 1.0 (2019)
[M+Na]+165.4437391
predicted
DarkChem Lite v0.1.0
[M+Na]+156.51544
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Prost F, Thormann W: Assessment of the stereoselective metabolism of methaqualone in man by capillary electrophoresis. Electrophoresis. 2003 Aug;24(15):2598-607. doi: 10.1002/elps.200305512. [Article]

Drug created at September 11, 2007 21:07 / Updated at February 21, 2021 18:51