GBR-12935

GBR-12935
Identifiers
IUPAC name
  • 1-(2-(diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H34N2O
Molar mass414.593 g·mol−1
3D model (JSmol)
SMILES
  • C1CN(CCN1CCCC2=CC=CC=C2)CCOC(C3=CC=CC=C3)C4=CC=CC=C4
InChI
  • InChI=1S/C28H34N2O/c1-4-11-25(12-5-1)13-10-18-29-19-21-30(22-20-29)23-24-31-28(26-14-6-2-7-15-26)27-16-8-3-9-17-27/h1-9,11-12,14-17,28H,10,13,18-24H2 ☒N
  • Key:RAQPOZGWANIDQT-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

GBR-12935 is a piperazine derivative which is a potent and selective dopamine reuptake inhibitor. It was originally developed in its 3H radiolabelled form for the purpose of mapping the distribution of dopaminergic neurons in the brain by selective labelling of dopamine transporter proteins.[1] This has led to potential clinical uses in the diagnosis of Parkinson's disease,[2] although selective radioligands such as Ioflupane (¹²³I) are now available for this application. GBR-12935 is now widely used in animal research into Parkinson's disease and the dopamine pathways in the brain.[3][4][5]

See also

References

  1. ↑ Berger P, Janowsky A, Vocci F, Skolnick P, Schweri MM, Paul SM (January 1985). "[3H]GBR-12935: a specific high affinity ligand for labeling the dopamine transport complex". European Journal of Pharmacology. 107 (2): 289–90. doi:10.1016/0014-2999(85)90075-5. PMID 3979428.
  2. ↑ Janowsky A, Vocci F, Berger P, Angel I, Zelnik N, Kleinman JE, et al. (August 1987). "[3H]GBR-12935 binding to the dopamine transporter is decreased in the caudate nucleus in Parkinson's disease". Journal of Neurochemistry. 49 (2): 617–21. doi:10.1111/j.1471-4159.1987.tb02908.x. PMID 3598589.
  3. ↑ Zhu J, Green T, Bardo MT, Dwoskin LP (January 2004). "Environmental enrichment enhances sensitization to GBR 12935-induced activity and decreases dopamine transporter function in the medial prefrontal cortex". Behavioural Brain Research. 148 (1–2): 107–17. doi:10.1016/s0166-4328(03)00190-6. PMID 14684252.
  4. ↑ Swant J, Wagner JJ (2006). "Dopamine transporter blockade increases LTP in the CA1 region of the rat hippocampus via activation of the D3 dopamine receptor". Learning & Memory. 13 (2): 161–7. doi:10.1101/lm.63806. PMC 1409827. PMID 16585791.
  5. ↑ Hsin LW, Chang LT, Rothman RB, Dersch CM, Jacobson AE, Rice KC (May 2008). "Design and synthesis of 2- and 3-substituted-3-phenylpropyl analogs of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine: role of amino, fluoro, hydroxyl, methoxyl, methyl, methylene, and oxo substituents on affinity for the dopamine and serotonin transporters". Journal of Medicinal Chemistry. 51 (9): 2795–806. doi:10.1021/jm701270n. PMC 5548119. PMID 18393401.
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