Etaqualone

Etaqualone
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: unscheduled;
Identifiers
	IUPAC name 3-(2-ethylphenyl)-2-methyl-quinazolin-4-one;
CAS Number	7432-25-9 ;
PubChem CID	23914;
ChemSpider	22357 ;
UNII	HFS3HB32J7;
ChEMBL	ChEMBL2104633 ;
CompTox Dashboard (EPA)	DTXSID60225333 ;
Chemical and physical data
Formula	C17H16N2O
Molar mass	264.328 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1C2=CC=CC=C2N=C(C)N1C3=CC=CC=C3CC;
	InChI InChI=1S/C17H16N2O/c1-3-13-8-4-7-11-16(13)19-12(2)18-15-10-6-5-9-14(15)17(19)20/h4-11H,3H2,1-2H3 ; Key:UVTJKLLUVOTSOB-UHFFFAOYSA-N ;
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Etaqualone (Aolan, Athinazone, Ethinazone^[1]) is a quinazolinone-class GABAergic and is an analogue of methaqualone that was developed in the 1960s^[2]^[3] and marketed mainly in France and some other European countries. It has sedative, hypnotic, muscle relaxant and central nervous system depressant properties resulting from its agonist activity at the β-subtype of the GABA_A receptor, and was used for the treatment of insomnia.

The dosage and effects are reported to be similar to those of methaqualone, but shorter acting and slightly weaker. Typical reports use between 50 and 500 mg of etaqualone, depending on desired effects. Old pharmaceutical formulations of Ethinazone were 350 mg tablets. Etaqualone is thought to act in a similar way to barbiturates and benzodiazepines by increasing the sensitivity of GABA_A receptors ^{[citation needed]}. Recreational effects include euphoria, relaxation, increased sociability and sexuality, reduction of short-term memory, and loss of coordination. Combination with other depressants has a potentiating effect and can cause overdose. Tolerance to benzodiazepines or alcohol will also reduce effects.

Ethaqualone can be present as a free base, insoluble in water but soluble in alcohol and nonpolar solvents, or as a water-soluble hydrochloride salt which is about 85% as potent as the freebase by weight ^{[citation needed]}.

The most common route of administration of etaqualone is oral, but snorting the salt or smoking the free base have also been reported ^{[citation needed]}.

References

^ Pflegel P, Wagner G (November 1967). "[On the polarography of 2-methyl-3-(2-methylphenyl)-3,4-dihydroquinazolinone-(4) methaqualone, Dormutil) and 2-methyl-3-(2-ethylphenyl-3,4-dihydroquinazolinone-(4) (ethinazone, Aolan). 5. Polarography of heterocyclic compounds]" [On the Polarography of 2-Methyl-3-(2-methylphenyl)-3,4-dihydroquinazolinone-(4) (methaqualone, Dormutil) and 2-methyl-3-(2-ethylphenyl-3,4-dihydroquinazolinone-(4) (ethinazone, Aolan). 5. Polarography of Heterocyclic Compounds]. Die Pharmazie (in German). 22 (11): 643–50. PMID 5619478.
^ GB patent 936902, "Quinazolinone Derivatives", issued 1963-09-18, assigned to Beiersdorf
^ Parmar SS, Kishor K, Seth PK, Arora RC (January 1969). "Role of alkyl substitution in 2,3-disubstituted and 3-substituted 4-quinazolones on the inhibition of pyruvic acid oxidation". Journal of Medicinal Chemistry. 12 (1): 138–41. doi:10.1021/jm00301a035. PMID 4303122.