MECLOQUALONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H11ClN2O
Molecular Weight	270.714
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(Cl)C=CC=C3

InChI

InChIKey=SFITWQDBYUMAPS-UHFFFAOYSA-N

InChI=1S/C15H11ClN2O/c1-10-17-13-8-4-2-6-11(13)15(19)18(10)14-9-5-3-7-12(14)16/h2-9H,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14406263 | https://www.ncbi.nlm.nih.gov/pubmed/13936358 | https://www.ncbi.nlm.nih.gov/pubmed/5353825 | https://www.ncbi.nlm.nih.gov/pubmed/5089785 | https://www.unodc.org/documents/scientific/Methaqualone_ST_NAR_15_Rev1.pdf | http://www.mdpi.com/1420-3049/22/2/188/htm | http://onlinelibrary.wiley.com/doi/10.1002/ddr.430070307/full

Mecloqualone is a quinazoline-class GABAergic and an analog of methaqualone. It acts as an agonist of the beta subtype of GABAa receptor and induces sedative, hypnotic and anxiolytic effects. Mecloqualone was marketed (mostly in france) under the names Nubrene and Casfen for the treatment of insomnia. Mecloqualone is no longer prescribed because of concerns about its potential for abuse and overdose. In the United States, it is registered as a Schedule-I non-narcotic controlled substance.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; agonist GABA site 13 Target ID: CHEMBL2109244 Sources: http://onlinelibrary.wiley.com/doi/10.1002/ddr.430070307/full \| http://www.mdpi.com/1420-3049/22/2/188/htm	Agonist 2637

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://www.unodc.org/documents/scientific/Methaqualone_ST_NAR_15_Rev1.pdf	Primary		Withdrawn	Nubarene Approved Use Mecloqualone was approved for treatment of insomnia in the 1960's. The potential for abuse lead to discontinuation and subsequent legal restrictions.

PubMed

Title	Date	PubMed
Some 2, 3-disubstituted 3H-4-quinazolones and 3H-4-thioquinazolones.	1960 Sep	14406263
[Clinical use of a new psycholeptic: Mecloqualone].	1963	13936358
Detection, assay and rate of excretion of mecloqualone in animals and man.	1969 Nov	5353825
[Hypnotic action of mecloqualone. Comparison with placebo effects and secobarbital].	1971 Apr 10	5089785

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

MECLOQUALONE

Official Name

English

MECLOQUALONE [MI]

Common Name

English

MECLOQUALONE [USAN]

Common Name

English

NSC-142005

Code

English

W-4744

Code

English

W 4744

Code

English

4(3H)-QUINAZOLINONE, 3-(2-CHLOROPHENYL)-2-METHYL-

Systematic Name

English

mecloqualone [INN]

Common Name

English

3-(O-CHLOROPHENYL)-2-METHYL-4(3H)-QUINAZOLINONE

Common Name

English

Classification Tree Code System Code

DEA NO.

2572