GBR-12935

Chemical compound
GBR-12935
Identifiers
  • 1-(2-(diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine
CAS Number
  • 76778-22-8 checkY
PubChem CID
  • 3456
IUPHAR/BPS
  • 4639
ChemSpider
  • 3338 ☒N
UNII
  • 9J9974WIBA
ChEBI
  • CHEBI:64093 ☒N
ChEMBL
  • ChEMBL26320 ☒N
CompTox Dashboard (EPA)
  • DTXSID2043743 Edit this at Wikidata
Chemical and physical data
FormulaC28H34N2O
Molar mass414.593 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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. S2CID 25654981.
  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. S2CID 20382190.
  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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AdamantanesAdenosine antagonistsAlkylaminesAmpakinesArylcyclohexylaminesBenzazepinesCathinonesCholinergicsConvulsantsEugeroicsOxazolinesPhenethylamines
PhenylmorpholinesPiperazinesPiperidinesPyrrolidinesRacetamsTropanesTryptaminesOthers
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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Simple piperazines
(no additional rings)
Phenylpiperazines
Benzylpiperazines
Diphenylalkylpiperazines
(benzhydrylalkylpiperazines)
Pyrimidinylpiperazines
Pyridinylpiperazines
Benzo(iso)thiazolylpiperazines
Tricyclics
(piperazine attached via side chain)
Others/Uncategorized
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