GBR-12935

GBR-12935
Identifiers
	IUPAC name 1-(2-(diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine;
CAS Number	76778-22-8 ;
PubChem CID	3456;
IUPHAR/BPS	4639;
ChemSpider	3338 ;
UNII	9J9974WIBA;
ChEBI	CHEBI:64093 ;
ChEMBL	ChEMBL26320 ;
CompTox Dashboard (EPA)	DTXSID2043743 ;
Chemical and physical data
Formula	C28H34N2O
Molar mass	414.593 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:RAQPOZGWANIDQT-UHFFFAOYSA-N ;
	(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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

[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.

[1]

[2]

[3]

[4]

[5]

Identifiers

IUPAC name 1-(2-(diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine
CAS Number	76778-22-8^Y
PubChem CID	3456
IUPHAR/BPS	4639
ChemSpider	3338^N
UNII	9J9974WIBA
ChEBI	CHEBI:64093^N
ChEMBL	ChEMBL26320^N
CompTox Dashboard (EPA)	DTXSID2043743
Chemical and physical data
Formula	C₂₈H₃₄N₂O
Molar mass	414.593 g·mol⁻¹
3D model (JSmol)	Interactive image
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
^NY (what is this?) (verify)

GBR-12935

See also

References