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Details

Stereochemistry ACHIRAL
Molecular Formula C16H14N2O
Molecular Weight 250.2952
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHAQUALONE

SMILES

CC1=NC2=CC=CC=C2C(=O)N1C3=C(C)C=CC=C3

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

Molecular Formula C16H14N2O
Molecular Weight 250.2952
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 The drug became banned in many countries and was withdrawn from many markets in the early 1980s.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
Semiautomatic quantification of angiogenesis.
2010 Jul
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:55:16 UTC 2023
Edited
by admin
on Sat Dec 16 17:55:16 UTC 2023
Record UNII
7ZKH8MQW6T
Record Status Validated (UNII)
Record Version
  • Download
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 [VANDF]
Common Name English
TR-495
Code English
CN-38703
Code English
Methaqualone [WHO-DD]
Common Name English
METHAQUALONE [EP IMPURITY]
Common Name 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 Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
WHO-VATC QN05CX02
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
DEA NO. 2565
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
NCI_THESAURUS C29756
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
WHO-ATC N05CM01
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
WHO-VATC QN05CM01
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
WHO-ATC N05CX02
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
Code System Code Type Description
SMS_ID
100000081228
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
MESH
D008702
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
NSC
111388
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
MERCK INDEX
m7302
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY Merck Index
HSDB
3120
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
CHEBI
6821
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL282052
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
DRUG BANK
DB04833
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
NSC
631628
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
NSC
126877
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
DRUG CENTRAL
1739
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
RXCUI
6823
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY RxNorm
PUBCHEM
6292
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
FDA UNII
7ZKH8MQW6T
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
INN
966
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
WIKIPEDIA
METHAQUALONE
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
EPA CompTox
DTXSID7023279
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
EVMPD
SUB08840MIG
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-780-4
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
NCI_THESAURUS
C640
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
CAS
72-44-6
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
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