Methaqualone

Methaqualone
Clinical data
Pronunciation	/mɛθəˈkweɪloʊn/
Trade names	Bon-Sonnil, Dormogen, Dormutil, Mequin, Mozambin, Pro Dorm, Quaalude, Somnotropon, Torinal, Tuazolona; Methaqualone hydrochloride:; Cateudyl, Dormir, Hyptor, Melsed, Melsedin, Mequelon, Methasedil, Nobadorm, Normorest, Noxybel, Optimil, Optinoxan, Pallidan, Parest, Parmilene, Pexaqualone, Renoval, Riporest, Sedalone, Somberol, Somnifac, Somnium, Sopor, Sovelin, Soverin, Sovinal, Toquilone, Toraflon, Tualone, Tuazol
ATC code	N05CM01 (WHO) ;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule III; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I; UN: Psychotropic Schedule II;
Pharmacokinetic data
Protein binding	70–80%
Elimination half-life	Biphasic (10–40; 20–60 hours)
Identifiers
	IUPAC name 2-Methyl-3-o-tolyl-4(3H)-quinazolinone;; 3,4-Dihydro-2-methyl-4-oxo-3-o-tolylquinazoline;; 2-Methyl-3-(2-methylphenyl)-4-(3H)-quinazolinone;
CAS Number	72-44-6 ;
PubChem CID	6292;
DrugBank	DB04833 ;
ChemSpider	6055 ;
UNII	7ZKH8MQW6T;
KEGG	D00557 ;
ChEMBL	ChEMBL282052 ;
CompTox Dashboard (EPA)	DTXSID7023279 ;
ECHA InfoCard	100.000.710
Chemical and physical data
Formula	C16H14N2O
Molar mass	250.301 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	113 °C (235 °F)
	SMILES Cc1ccccc1-n1c(C)nc2ccccc2c1=O;
	InChI 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 ; Key:JEYCTXHKTXCGPB-UHFFFAOYSA-N ;
	(verify)

Methaqualone is a hypnotic sedative. It was sold under the brand names Quaalude (/ˈkweɪluːd/ KWAY-lood) and Sopor among others, which contained 300 mg of methaqualone, and sold as a combination drug under the brand name Mandrax, which contained 250 mg methaqualone and 25 mg diphenhydramine within the same tablet, mostly in Europe. Commercial production of methaqualone was halted in the mid-1980s due to widespread abuse and addictiveness. It is a member of the quinazolinone class.

The sedative–hypnotic activity of methaqualone was recognized in 1955. In 1962, methaqualone was patented in the United States by Wallace and Tiernan.^[2] Its use peaked in the early 1970s for the treatment of insomnia, and as a sedative and muscle relaxant.

Methaqualone became increasingly popular as a recreational drug and club drug in the late 1960s and 1970s, known variously as "ludes" or "disco biscuits"^[3] due to its widespread use during the popularity of disco in the 1970s, or "sopers" (also "soaps") in the United States and Canada, and "mandrakes" and "mandies" in the United Kingdom, Australia and New Zealand. The substance was sold both as a free base and as a salt (hydrochloride). This use means the drug is controlled in most countries, and is so under Schedule II of the United Nations Convention on Psychotropic Substances.

^ 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.
^ U.S. patent 3,135,659
^ Bekiempis V (August 2, 2015). "Do People Still Take Quaaludes?". Newsweek. NEWSWEEK DIGITAL LLC. Retrieved 22 July 2023.

[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] U.S. patent 3,135,659

[newsweek-3] Bekiempis V (August 2, 2015). "Do People Still Take Quaaludes?". Newsweek. NEWSWEEK DIGITAL LLC. Retrieved 22 July 2023.

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