thozalinone

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470609358

| IUPAC_name = (RS)-2-(Dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one

| image = Thozalinone.svg

| image_class = skin-invert-image

| alt = Skeletal formula

| image2 = Thozalinone molecule spacefill.png

| image_class2 = bg-transparent

| alt2 = Space-filling model

| width2 = 155

| width = 200px

| chirality = Racemic mixture

| tradename =

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 655-05-0

| ATC_prefix = none

| ATC_suffix =

| PubChem = 12602

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

| ChemSpiderID = 12082

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

| UNII = 68X5932947

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D06115

| ChEMBL = 2105457

| synonyms = Tozalinone, Thozalinon

| C=11 | H=12 | N=2 | O=2

| smiles = O=C2\N=C(/OC2c1ccccc1)N(C)C

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

| StdInChI = 1S/C11H12N2O2/c1-13(2)11-12-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,1-2H3

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

| StdInChIKey = JJSHYECKYLDYAR-UHFFFAOYSA-N

}}

Thozalinone (USAN) (brand name Stimsen; former developmental code name CL-39808) is a psychostimulant that has been used as an antidepressant in Europe.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA435|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=435–}}{{cite journal | vauthors = Greenblatt EN, Osterberg AC | title = Some pharmacologic properties of thozalinone, a new excitant | journal = Toxicology and Applied Pharmacology | volume = 7 | issue = 4 | pages = 566–78 | date = July 1965 | pmid = 4378772 | doi = 10.1016/0041-008X(65)90042-6 }}{{cite book | title = Dictionary of organic compounds | publisher = Chapman & Hall | location = London | year = 1996 | isbn = 0-412-54090-8 | url = https://books.google.com/books?id=C3Uo1co4Wv0C&q=thozalinone&pg=PA2539 | access-date = 2021-05-31 | archive-date = 2021-05-31 | archive-url = https://web.archive.org/web/20210531152758/https://books.google.com/books?id=C3Uo1co4Wv0C&q=thozalinone&pg=PA2539 | url-status = live }}{{cite book | title = Merck index on CD-ROM: Windows | publisher = Chapman & Hall EPD | location = London | year = 1998 | isbn = 0-412-82910-X }}{{cite journal | vauthors = Gallant DM, Bishop MP, Scrignar CB, Hornsby L, Moore B, Inturrisi BB | title = A double-blind study of thozalinone (C1 39,808) in depressed outpatients | journal = Current Therapeutic Research, Clinical and Experimental | volume = 8 | issue = 12 | pages = 621–2 | date = December 1966 | pmid = 4962734 }} It has also been trialed as an anorectic.{{cite journal | vauthors = Leite AC, Liepen LL, Costa VP | title = [Clinical trial of Stimsem Thozalinone in the treatment of obese patients] | language = pt | journal = Revista Brasileira de Medicina | volume = 28 | issue = 9 | pages = 475–8 | date = September 1971 | pmid = 5139648 }} Thozalinone is described as a "dopaminergic stimulant",{{cite journal | vauthors = Yen-Koo HC, Balazs T | title = Detection of dopaminergic supersensitivity induced by neuroleptic drugs in mice | journal = Drug and Chemical Toxicology | volume = 3 | issue = 2 | pages = 237–47 | year = 1980 | pmid = 6112126 | doi = 10.3109/01480548009108286 }} and likely acts via inducing the release of dopamine and to a minimal extent norepinephrine; similar to analogue pemoline, it is reportedly devoid of abuse potential unlike other dopaminergic psychostimulants.{{cite journal | vauthors = Yen-Koo HC, Davis DA, Balazs T | title = Inhibition of dopaminergic agonist-induced gnawing behavior by neuroleptic drugs in mice | journal = Drug and Chemical Toxicology | volume = 8 | issue = 6 | pages = 495–502 | year = 1985 | pmid = 2868876 | doi = 10.3109/01480548509041072 }}