GYKI 52895

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 449582997

| IUPAC_name = 4-{13-methyl-4,6-dioxa-11,12-diazatricyclo[7.5.0.0^3,7]tetradeca-1,3(7),8,10-tetraen-10-yl}aniline

| image = GYKI 52895.svg

| width = 200

| image2 = GYKI-52895-3d.png

| tradename =

| legal_status =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 869360-93-0

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

| UNII = H7KSE29GCH

| PubChem = 3539

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

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

| ChemSpiderID = 3418

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

| KEGG = C15094

| ChEMBL = 1256984

| C=17 | H=17 | N=3 | O=2

| smiles = O1c2c(OC1)cc3c(c2)C(=N/NC(C3)C)\c4ccc(N)cc4

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

| StdInChI = 1S/C17H17N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8,10,19H,6,9,18H2,1H3

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

| StdInChIKey = AQTITSBNGSVQNZ-UHFFFAOYSA-N

| synonyms = 4-(8,9-Dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine

}}

GYKI 52895 is a drug which is a 2,3-benzodiazepine derivative that also shares the 3,4-methylenedioxyamphetamine pharmacophore. Unlike other similar drugs, GYKI 52895 is a selective dopamine reuptake inhibitor (DARI),{{cite journal | vauthors = Horváth K, Szabó H, Pátfalusi M, Berzsenyi P, Andrási F | title = Pharmacological Effects of GYKI 52895, a New Selective Dopamine Uptake Inhibitor. | journal = European Journal of Pharmacology | date = 1990 | volume = 183 | issue = 4 | pages = 1416–1417 | doi = 10.1016/0014-2999(90)94548-C }}{{cite journal | vauthors = Huang CL, Chen HC, Huang NK, Yang DM, Kao LS, Chen JC, Lai HL, Chern Y | display-authors = 6 | title = Modulation of dopamine transporter activity by nicotinic acetylcholine receptors and membrane depolarization in rat pheochromocytoma PC12 cells | journal = Journal of Neurochemistry | volume = 72 | issue = 6 | pages = 2437–44 | date = June 1999 | pmid = 10349853 | doi = 10.1046/j.1471-4159.1999.0722437.x | doi-access = free }} which appears to have an atypical mode of action compared to other DARIs.{{cite journal | vauthors = Vaarmann A, Gandhi S, Gourine AV, Abramov AY | title = Novel pathway for an old neurotransmitter: dopamine-induced neuronal calcium signalling via receptor-independent mechanisms | journal = Cell Calcium | volume = 48 | issue = 2–3 | pages = 176–82 | date = 2010 | pmid = 20846720 | doi = 10.1016/j.ceca.2010.08.008 }} Its DRI activity is shared by numerous addictive drugs including amphetamine and its derivatives (e.g. dextromethamphetamine), cocaine, and methylphenidate and its derivatives (e.g. ethylphenidate). However, dopaminergic drugs are also prone to producing emetic effects such as in the case of apomorphine.

Egis Pharmaceuticals began clinical development of the drug in 1997 for major depressive disorder and Parkinson's disease, but it was discontinued in 2001.{{Cite web | url = https://adisinsight.springer.com/drugs/800001417 | title = GYKI 52895 | publisher = Adis Insight }}