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Details

Stereochemistry ACHIRAL
Molecular Formula C16H14N2O
Molecular Weight 250.2958
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHAQUALONE

SMILES

Cc1ccccc1-n2c(C)nc3ccccc3c2=O

InChI

InChIKey=JEYCTXHKTXCGPB-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including: http://www.encyclopedia.com/science/applied-and-social-sciences-magazines/methaqualone | https://www.ncbi.nlm.nih.gov/pubmed/26056160 | https://addictionlibrary.org/prescription/mandrax-uses-symptoms-signs-and-addiction-treatment.html

Methaqualone is a depressant that modulates the activity of the GABA receptors in the brain and nervous system. It promotes relaxation, sleepiness and sometimes a feeling of euphoria. It causes a drop in blood pressure and slows the pulse rate. These properties are the reason why it was initially thought to be a useful sedative and anxiolytic. Common side effects of Methaqualone include dizziness, nausea, vomiting, diarrhea, abdominal cramps, fatigue, itching, rashes, sweating, dry mouth, tingling sensation in arms and legs, seizures and its depressant effects include reduced heart rate and respiration. The drug became banned in many countries and was withdrawn from many markets in the early 1980s.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: GABA A receptor alpha-6/beta-1/delta
4.0 null [pEC50]
Target ID: GABA A receptor alpha-4/beta-2/delta
4.17 null [pEC50]
Target ID: GABA A receptor alpha-4/beta-3/delta
3.91 null [pEC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Quaalude

Approved Use

Methaqualone is indicated for the treatment of anxiety and sleep disorders.

Launch Date

-5.04921588E11
Primary
Quaalude

Approved Use

Methaqualone is indicated for the treatment of anxiety and sleep disorders.

Launch Date

-5.04921588E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.1 μg/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHAQUALONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
46.7 μg × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHAQUALONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHAQUALONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
PubMed

PubMed

TitleDatePubMed
Extrapyramidal reaction in a patient on combined drug therapy: report of a case.
1971 Jul-Aug
Seven cases of somnambulism induced by drugs.
1979 Jul
Synthesis and anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones.
1990 Jan
A survey of reported synthesis of methaqualone and some positional and structural isomers.
2001 Nov 1
Molecular epidemiology of multidrug-resistant tuberculosis, New York City, 1995-1997.
2002 Nov
Chinese red yeast rice (Monascus purpureus) for primary hyperlipidemia: a meta-analysis of randomized controlled trials.
2006 Nov 23
A case of acute myeloid leukemia-M2 with trisomy 4 in addition to t(8;21).
2008 Jan
Rosiglitazone: can meta-analysis accurately estimate excess cardiovascular risk given the available data? Re-analysis of randomized trials using various methodologic approaches.
2009 Jan 10
A new recurring chromosome 13 abnormality in two older patients with de novo acute myeloid leukemia: An Indian experience.
2009 Sep
HypoCol (red yeast rice) lowers plasma cholesterol - a randomized placebo controlled study.
2010 Aug
The Summary Index of Malaria Surveillance (SIMS): a stable index of malaria within India.
2010 Feb 11
Semiautomatic quantification of angiogenesis.
2010 Jul
Retrospective cohort study of a new infant formula during the first 6 months of life: reflections on growth curves, human milk and formula feeding.
2010 Nov
Patents

Sample Use Guides

75-150 mg sedation. A commonly prescribed dose was 300 mg. Up to 600 mg was used for strong sedation.
Route of Administration: Oral
Methaqualone displayed bell-shaped concentration-response curves as a positive allosteric modulator at all receptors when coapplied with GABA EC10 in concentrations ranging from 1 to 1000 uM (exemplified for a1b2g2S and a6b2delta. Pronounced rebound currents were observed at methaqualone concentrations of 300 uM and greater.
Name Type Language
METHAQUALONE
EP   HSDB   INN   JAN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
METHAQUALONE [USAN]
Common Name English
4(3H)-QUINAZOLINONE, 2-METHYL-3-(2-METHYLPHENYL)-
Systematic Name English
R-148
Code English
CI-705
Code English
NSC-126877
Code English
METHAQUALONE [MI]
Common Name English
QZ-2
Code English
NSC-111388
Code English
METHAQUALONE [WHO-DD]
Common Name English
METHAQUALONE [VANDF]
Common Name English
NSC-111388-
Code English
METHAQUALONE [EP]
Common Name English
TR-495
Code English
CN-38703
Code English
METOLQUIZOLONE
Common Name English
METHAQUALONE [INN]
Common Name English
NSC-631628
Code English
METHAQUALONEINONE
Common Name English
METHAQUALONE [MART.]
Common Name English
2-METHYL-3-O-TOLYL-4(3H)-QUINAZOLINONE
Common Name English
CN 38703
Code English
METHAQUALONE [JAN]
Common Name English
METHAQUALONE [HSDB]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 862.3630
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
WHO-VATC QN05CX02
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
DEA NO. 2565
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
NCI_THESAURUS C29756
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
WHO-ATC N05CM01
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
WHO-VATC QN05CM01
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
WHO-ATC N05CX02
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
Code System Code Type Description
MESH
D008702
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
MERCK INDEX
M7302
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY Merck Index
HSDB
3120
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
ChEMBL
CHEMBL282052
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
DRUG BANK
DB04833
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
DRUG CENTRAL
1739
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
RXCUI
6823
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY RxNorm
PUBCHEM
6292
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PRIMARY
FDA UNII
7ZKH8MQW6T
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
INN
966
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
WIKIPEDIA
METHAQUALONE
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
EPA CompTox
72-44-6
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
EVMPD
SUB08840MIG
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-780-4
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
NCI_THESAURUS
C640
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY
CAS
72-44-6
Created by admin on Fri Jun 25 20:33:14 UTC 2021 , Edited by admin on Fri Jun 25 20:33:14 UTC 2021
PRIMARY