GYKI 52895

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),^[1][2] which appears to have an atypical mode of action compared to other DARIs.^[3] 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.

GYKI 52895

Clinical data
Other names	4-(8,9-Dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine
Identifiers
IUPAC name 4-{13-methyl-4,6-dioxa-11,12-diazatricyclo[7.5.0.03,7]tetradeca-1,3(7),8,10-tetraen-10-yl}aniline
CAS Number	869360-93-0 Y
PubChem CID	3539
ChemSpider	3418 Y
UNII	H7KSE29GCH
KEGG	C15094 Y
ChEMBL	ChEMBL1256984
CompTox Dashboard (EPA)	DTXSID80921385
Chemical and physical data
Formula	C17H17N3O2
Molar mass	295.342 g·mol−1
3D model (JSmol)	Interactive image
SMILES O1c2c(OC1)cc3c(c2)C(=N/NC(C3)C)\c4ccc(N)cc4
InChI InChI=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 Y Key:AQTITSBNGSVQNZ-UHFFFAOYSA-N Y
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Egis Pharmaceuticals began clinical development of the drug in 1997 for major depressive disorder and Parkinson's disease, but it was discontinued in 2001.^[4]

See also

• GYKI 52466, another 2,3-benzodiazepine with other than GABAergic function
• Tifluadom
• Lufuradom
• Benzodiazepine
• Substituted methylenedioxyphenethylamine

References

1. Horváth K, Szabó H, Pátfalusi M, Berzsenyi P, Andrási F (1990). "Pharmacological Effects of GYKI 52895, a New Selective Dopamine Uptake Inhibitor". European Journal of Pharmacology. 183 (4): 1416–1417. doi:10.1016/0014-2999(90)94548-C.
2. Huang CL, Chen HC, Huang NK, Yang DM, Kao LS, Chen JC, et al. (June 1999). "Modulation of dopamine transporter activity by nicotinic acetylcholine receptors and membrane depolarization in rat pheochromocytoma PC12 cells". Journal of Neurochemistry. 72 (6): 2437–44. doi:10.1046/j.1471-4159.1999.0722437.x. PMID 10349853.
3. Vaarmann A, Gandhi S, Gourine AV, Abramov AY (2010). "Novel pathway for an old neurotransmitter: dopamine-induced neuronal calcium signalling via receptor-independent mechanisms". Cell Calcium. 48 (2–3): 176–82. doi:10.1016/j.ceca.2010.08.008. PMID 20846720.
4. "GYKI 52895". Adis Insight.