METHAQUALONE

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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 The drug became banned in many countries and was withdrawn from many markets in the early 1980s.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	Negative Allosteric Modulator 42	4.0 null [pEC50]
GABA A receptor alpha-4/beta-2/delta 2	Positive Allosteric Modulator 179	4.17 null [pEC50]
GABA A receptor alpha-4/beta-3/delta 2	Agonist 2,678	3.91 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108	Primary		Approved 8,429	Quaalude
Anxiety 267	Primary		Approved 8,429	Quaalude

C_max

Value	Dose	Co-administered	Analyte	Population
3.1 μg/mL	300 mg single, oral		METHAQUALONE serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
46.7 μg × h/mL	300 mg single, oral		METHAQUALONE serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
19 h	300 mg single, oral		METHAQUALONE serum	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037	substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 349 CYP1A2 1,054 CYP2C19 991 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2E1 667 CYP4A 2

Drug as victim

Show entries

Target	Modality	Activity
CYP1A1 349	substrate 3,367	likely
CYP1A2 1,054	substrate 3,367	likely
CYP2C19 991	substrate 3,367	likely
CYP2C9 1,037	substrate 3,367	likely
CYP3A4 1,737	substrate 3,367	major

Showing 1 to 5 of 11 entries

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Sourcing

Sourcing

Show entries

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

Showing 1 to 3 of 3 entries

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PubMed

Show entries

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
A new recurring chromosome 13 abnormality in two older patients with de novo acute myeloid leukemia: An Indian experience.	2009 Sep	21088719
The Summary Index of Malaria Surveillance (SIMS): a stable index of malaria within India.	2010 Feb 11	20181218

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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.