Mecloqualone

Mecloqualone (Nubarene, Casfen) is a Quinazolinone-class GABAergic and is an analogue of methaqualone that was first made in 1960[1] and marketed mainly in France and some other European countries. It has sedative, hypnotic, and anxiolytic properties caused by its agonist activity at the β subtype of the GABAa receptor, and was used for the treatment of insomnia.[2] Mecloqualone is faster-acting but shorter-lasting than methaqualone and so was used only as a sleeping pill,[3] in contrast to methaqualone, which was used as a general-purpose anxiolytic as well. Mecloqualone was never as widely used as methaqualone and is no longer prescribed because of concerns about its potential for abuse and overdose. In the United States it is a Schedule I non-narcotic (depressant) controlled substance with an ACSCN of 2572 and 30 g[4] annual aggregate manufacturing quota.

Mecloqualone
Clinical data
ATC code
  • none
Legal status
Legal status
  • CA: Schedule III
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class B
  • US: Schedule I
  • UN: Psychotropic Schedule II
Identifiers
IUPAC name
  • 3-(2-chlorophenyl)-2-methylquinazolin-4(3H)-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.848
Chemical and physical data
FormulaC15H11ClN2O
Molar mass270.714 g·mol−1
3D model (JSmol)
SMILES
  • Clc3ccccc3N/1C(=O)c2c(\N=C\1C)cccc2
InChI
  • 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 Y
  • Key:SFITWQDBYUMAPS-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

See also

References
  1. Jackman GB, Petrow V, Stephenson O (September 1960). "Some 2, 3-disubstituted 3H-4-quinazolones and 3H-4-thioquinazolones". The Journal of Pharmacy and Pharmacology. 12: 529–38. doi:10.1111/j.2042-7158.1960.tb12705.x. PMID 14406263. S2CID 31254238.
  2. Mouren P, Giraud F, Pinsard N (1963). "[Clinical use of a new psycholeptic: Mecloqualone]". Marseille Medical. 100: 599–602. PMID 13936358.
  3. Dubnk B, Towne CA, Bush MT (November 1969). "Detection, assay and rate of excretion of mecloqualone in animals and man". Toxicology and Applied Pharmacology. 15 (3): 632–41. doi:10.1016/0041-008X(69)90065-9. PMID 5353825.
  4. "Established Aggregate Production Quotas for Schedule I and II Controlled Substances and Assessment of Annual Needs for the List I Chemicals Ephedrine, Pseudoephedrine, and Phenylpropanolamine for 2022".{{cite web}}: CS1 maint: url-status (link)
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