etaqualone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447759780

| IUPAC_name = 3-(2-ethylphenyl)-2-methyl-quinazolin-4-one

| image = Etaqualone.svg

| width = 200

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Unscheduled

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 7432-25-9

| ATC_prefix = none

| ATC_suffix =

| PubChem = 23914

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104633

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 22357

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = HFS3HB32J7

| C=17 | H=16 | N=2 | O=1

| smiles = O=C1C2=CC=CC=C2N=C(C)N1C3=CC=CC=C3CC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UVTJKLLUVOTSOB-UHFFFAOYSA-N

}}

Etaqualone (Aolan, Athinazone, Ethinazone{{cite journal | vauthors = Pflegel P, Wagner G | title = [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] | language = German | journal = Die Pharmazie | volume = 22 | issue = 11 | pages = 643–50 | date = November 1967 | pmid = 5619478 | trans-title = 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 }}) is a quinazolinone-class GABAergic and is an analogue of methaqualone that was developed in the 1960s.{{ cite patent | assign1 = Beiersdorf | title = Quinazolinone Derivatives | gdate = 1963-09-18 | country = GB | status = patent | number = 936902 }}{{cite journal | vauthors = Parmar SS, Kishor K, Seth PK, Arora RC | title = Role of alkyl substitution in 2,3-disubstituted and 3-substituted 4-quinazolones on the inhibition of pyruvic acid oxidation | journal = Journal of Medicinal Chemistry | volume = 12 | issue = 1 | pages = 138–41 | date = January 1969 | pmid = 4303122 | doi = 10.1021/jm00301a035 }} It was primarily marketed in France and other European countries,{{cite journal |vauthors=Yang H, Wang Y, Liu J, Qiu S, Gu J, Bai H, Li J, Wurita A, Hasegawa K |title=The next addiction-causing drug class 4-quinazolinone derivatives: analyses of methaqualone analogs including recently discovered 2-methoxyqualone by different modes of mass spectrometry |journal=Forensic Toxicology |volume=41 |issue=1 |pages=59–70 |date=January 2023 |pmid=36652055 |doi=10.1007/s11419-022-00631-z |url=}} as well as later in China, where it is still used clinically as of 2022.{{cite journal |vauthors=Yang H, Dai L, Wang Y, Liu J, Qiu S, Gu J, Bai H, Wurita A, Liao L |title=Analytical method for detection and quantification of new emerging drug etaqualone in human blood and urine by gas chromatography tandem mass spectrometry |journal=Legal Medicine (Tokyo, Japan) |volume=59 |issue= |pages=102125 |date=November 2022 |pmid=35932525 |doi=10.1016/j.legalmed.2022.102125}}{{cite journal |vauthors=Hongkun Y, Jinlei L, Lina D, Yue W, Junmei W, Wurita A |title=Detection and quantification of psychotropic drug etaqualone in human hair using GC-MS/MS |journal=Legal Medicine (Tokyo, Japan) |volume=53 |issue= |pages=101964 |date=November 2021 |pmid=34521032 |doi=10.1016/j.legalmed.2021.101964}} 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|date=April 2019}}. 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|date=September 2024}}.

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|date=September 2024}}.