GYKI-52895

GYKI-52895 is a drug which is a 2,3-benzodiazepine derivative that also shares the 3,4-Methylenedioxyphenethylamine 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[7.5.0.0^3,7]tetradeca-1,3(7),8,10-tetraen-10-yl}aniline
CAS Number	869360-93-0^Y
PubChem CID	3539
ChemSpider	3418^Y
KEGG	C15094^Y
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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See also

• GYKI-52,466, 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.
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.