GYKI 52895

Chemical compound
GYKI 52895
Clinical data
Other names4-(8,9-Dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine
Identifiers
  • 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 checkY
PubChem CID
  • 3539
ChemSpider
  • 3418 checkY
UNII
  • H7KSE29GCH
KEGG
  • C15094 checkY
ChEMBL
  • ChEMBL1256984
CompTox Dashboard (EPA)
  • DTXSID80921385 Edit this at Wikidata
Chemical and physical data
FormulaC17H17N3O2
Molar mass295.342 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 checkY
  • Key:AQTITSBNGSVQNZ-UHFFFAOYSA-N checkY
  (verify)

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.

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

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.
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(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
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See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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1,4-Benzodiazepines
1,5-Benzodiazepines
2,3-Benzodiazepines*
Triazolobenzodiazepines
Imidazobenzodiazepines
Oxazolobenzodiazepines
Thienodiazepines
Thienotriazolodiazepines
Thienobenzodiazepines*
Pyridodiazepines
Pyridotriazolodiazepines
Pyrazolodiazepines
Pyrrolodiazepines
Tetrahydroisoquinobenzodiazepines
Pyrrolobenzodiazepines*
Benzodiazepine prodrugs
* atypical activity profile (not GABAA receptor ligands)