METHAQUALONE

US Previously Marketed

First approved in 1962

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 Search

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

Description
Sources: https://www.drugs.com/illicit/quaaludes.html
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 The drug became banned in many countries and was withdrawn from many markets in the early 1980s.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
GABA A receptor alpha-6/beta-1/delta 2 Target ID: GABA A receptor alpha-6/beta-1/delta Sources: https://www.ncbi.nlm.nih.gov/pubmed/26056160	Negative Allosteric Modulator 42	4.0 null [pEC50]
GABA A receptor alpha-4/beta-2/delta 2 Target ID: GABA A receptor alpha-4/beta-2/delta Sources: https://www.ncbi.nlm.nih.gov/pubmed/26056160	Positive Allosteric Modulator 179	4.17 null [pEC50]
GABA A receptor alpha-4/beta-3/delta 2 Target ID: GABA A receptor alpha-4/beta-3/delta Sources: https://www.ncbi.nlm.nih.gov/pubmed/26056160	Agonist 2678	3.91 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13733024	Primary		Approved 8429	Quaalude Approved Use Methaqualone is indicated for the treatment of anxiety and sleep disorders. Launch Date 1954
Anxiety 267 Sources: https://www.drugs.com/illicit/quaaludes.html	Primary		Approved 8429	Quaalude Approved Use Methaqualone is indicated for the treatment of anxiety and sleep disorders. Launch Date 1954

C_max

Value	Dose	Co-administered	Analyte	Population
3.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4427217/	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

Value	Dose	Co-administered	Analyte	Population
46.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4427217/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4427217/	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 349 CYP1A2 1054 CYP2C19 991 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2E1 667 CYP4A 2

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	likely
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	likely
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	likely
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	likely
CYP3A4 1737	substrate 3367 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000072446, https://pubmed.ncbi.nlm.nih.gov/12900872/	major
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	minor
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no
CYP4A 2	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12900872/	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6821	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6821
ZINC	ZINC000002568176	http://zinc15.docking.org/substances/ZINC000002568176
eMolecules	757583	https://www.emolecules.com/cgi-bin/more?vid=757583

PubMed

Title	Date	PubMed
Extrapyramidal reaction in a patient on combined drug therapy: report of a case.	1971 Jul-Aug	5284823
Seven cases of somnambulism induced by drugs.	1979 Jul	453369
Synthesis and anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones.	1990 Jan	2296016
A survey of reported synthesis of methaqualone and some positional and structural isomers.	2001 Nov 1	11672968
Molecular epidemiology of multidrug-resistant tuberculosis, New York City, 1995-1997.	2002 Nov	12453347
Chinese red yeast rice (Monascus purpureus) for primary hyperlipidemia: a meta-analysis of randomized controlled trials.	2006 Nov 23	17302963
A case of acute myeloid leukemia-M2 with trisomy 4 in addition to t(8;21).	2008 Jan	20300287
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	19134216
A new recurring chromosome 13 abnormality in two older patients with de novo acute myeloid leukemia: An Indian experience.	2009 Sep	21088719
HypoCol (red yeast rice) lowers plasma cholesterol - a randomized placebo controlled study.	2010 Aug	20636227
The Summary Index of Malaria Surveillance (SIMS): a stable index of malaria within India.	2010 Feb 11	20181218
Semiautomatic quantification of angiogenesis.	2010 Jul	19345375
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	21243867

Patents

Sample Use Guides

In Vivo Use Guide

75-150 mg sedation. A commonly prescribed dose was 300 mg. Up to 600 mg was used for strong sedation.

Route of Administration: Oral

In Vitro Use Guide

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

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