Etaqualone

Etaqualone

Systematic (IUPAC) name
3-(2-ethylphenyl)-2-methyl-quinazolin-4-one
Clinical data
Routes of administration	Oral
Legal status	Unscheduled
Identifiers
CAS Number	7432-25-9
ATC code	none
PubChem	CID 23914
ChemSpider	22357
UNII	HFS3HB32J7
ChEMBL	CHEMBL2104633
Chemical data
Formula	C17H16N2O
Molar mass	264.322
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. 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.

The most common route of administration of ethaqualone is oral, but snorting the salt or smoking the free base have also been reported.

See also

• Methaqualone
• Methylmethaqualone
• Mecloqualone
• Mebroqualone
• Cloroqualone
• Diproqualone
• Afloqualone
• Nitromethaqualone
• SL-164
• Gamma-Aminobutyric acid

References

1. Pflegel, P.; Wagner, G. (1967). "(title in German)" [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): 643–650. PMID 5619478.
2. GB patent 936902, "Quinazolinone Derivatives", issued 1963-09-18, assigned to Beiersdorf 
3. Parmar, S. S.; Kishor, K.; Seth, P. K.; Arora, R. C. (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): 138–141. doi:10.1021/jm00301a035. PMID 4303122.