Mecloqualone

Mecloqualone
Clinical data
ATC code	none;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); 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	340-57-8 ;
PubChem CID	9567;
ChemSpider	9192 ;
UNII	09XU4VDV7E;
KEGG	D04877 ;
ChEMBL	ChEMBL279960 ;
CompTox Dashboard (EPA)	DTXSID7048875 ;
ECHA InfoCard	100.005.848
Chemical and physical data
Formula	C15H11ClN2O
Molar mass	270.72 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:SFITWQDBYUMAPS-UHFFFAOYSA-N ;
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Mecloqualone (Nubarene, Casfen) is a quinazolinone-class GABAergic and is an analogue of methaqualone that was first made in 1960^[2] 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 GABA_a receptor, and was used for the treatment of insomnia.^[3] Mecloqualone is faster-acting but shorter-lasting than methaqualone and so was used only as a sleeping pill,^[4] 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 grams^[5] annual aggregate manufacturing quota.

References

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ 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.
^ Mouren P, Giraud F, Pinsard N (1963). "[Clinical use of a new psycholeptic: Mecloqualone]". Marseille Medical. 100: 599–602. PMID 13936358.
^ 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.
^ "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".

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[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] 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.

[3] Mouren P, Giraud F, Pinsard N (1963). "[Clinical use of a new psycholeptic: Mecloqualone]". Marseille Medical. 100: 599–602. PMID 13936358.

[4] 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.

[5] "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".

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Mecloqualone

See also

References

zproxy.org

Clinical data

ATC code	none
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)^[1] 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	340-57-8^N
PubChem CID	9567
ChemSpider	9192^Y
UNII	09XU4VDV7E
KEGG	D04877^Y
ChEMBL	ChEMBL279960^Y
CompTox Dashboard (EPA)	DTXSID7048875
ECHA InfoCard	100.005.848
Chemical and physical data
Formula	C₁₅H₁₁ClN₂O
Molar mass	270.72 g·mol⁻¹
3D model (JSmol)	Interactive image
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)