Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C28H34N2O |
| Molecular Weight | 414.5824 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C(CN1CCN(CCOC(C2=CC=CC=C2)C3=CC=CC=C3)CC1)CC4=CC=CC=C4
InChI
InChIKey=RAQPOZGWANIDQT-UHFFFAOYSA-N
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
GBR-12935 (1-{2-benzhydryloxyethyl}-4-(3-phenylpropyl)piperazine) is a potent and selective inhibitor of dopamine transporter. Gist-Brocades originally initiated studies of GBR-12935 for the treatment of cocaine dependence.
Tritium-labeled GBR-12935 may be used in radioligand binding studies. GBR-12935 is considered to be the metabolite of vanoxerine, another piperazine dopamine uptake inhibitor.
Originator
Sources: Van der Zee P, Koger HS, Gootjes J, Hespe W. Aryl 1,4 -dialk(en)ylpiperazines as selective and very potent inhibitors of dopamine uptake. Eur J Med Chem. 1980;15:363–370.
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2225585/#R21 | https://www.ncbi.nlm.nih.gov/pubmed/3221529 | https://books.google.ru/books?id=eTu4VFQ4usgC&printsec=frontcover&hl=ru#v=onepage&q&f=false | https://www.ncbi.nlm.nih.gov/pubmed/11249581
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacological heterogeneity of the cloned and native human dopamine transporter: disassociation of [3H]WIN 35,428 and [3H]GBR 12,935 binding. | 1994 Jan |
|
| Effects of benztropine on behavioral and toxic effects of cocaine: comparison with atropine and the selective dopamine uptake inhibitor 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenyl-propyl)-piperazine. | 1996 Apr |
|
| Dopaminergic activity in transgenic mice underexpressing glucocorticoid receptors: effect of antidepressants. | 2001 |
|
| Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens. | 2001 Feb 23 |
|
| Expansion of structure-activity studies of piperidine analogues of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (GBR 12935) compounds by altering substitutions in the N-benzyl moiety and behavioral pharmacology of selected molecules. | 2002 Jan 31 |
|
| Development of long-acting dopamine transporter ligands as potential cocaine-abuse therapeutic agents: chiral hydroxyl-containing derivatives of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine. | 2002 Mar 14 |
|
| Chronic inhibition of the norepinephrine transporter in the brain participates in seizure sensitization to cocaine and local anesthetics. | 2003 Feb 21 |
|
| Pharmacological characterization of N,N-dimethyl-2-(2-amino-4-methylphenyl thio)benzylamine as a ligand of the serotonin transporter with high affinity and selectivity. | 2003 Jan |
|
| High affinity hydroxypiperidine analogues of 4-(2-benzhydryloxyethyl)-1-(4-fluorobenzyl)piperidine for the dopamine transporter: stereospecific interactions in vitro and in vivo. | 2003 Mar 27 |
|
| Presynaptic control of striatal dopamine neurotransmission in adult vesicular monoamine transporter 2 (VMAT2) mutant mice. | 2003 May |
|
| Uptake inhibitors but not substrates induce protease resistance in extracellular loop two of the dopamine transporter. | 2004 Mar |
|
| Influence of paraquat on dopaminergic transporter in the rat brain. | 2005 May-Jun |
|
| A slowly developing dysfunction of dopaminergic nigrostriatal neurons induced by long-term paraquat administration in rats: an animal model of preclinical stages of Parkinson's disease? | 2005 Sep |
|
| Toxic influence of subchronic paraquat administration on dopaminergic neurons in rats. | 2007 Jun 25 |
|
| Nanomolar propofol stimulates glutamate transmission to dopamine neurons: a possible mechanism of abuse potential? | 2008 Apr |
|
| 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. | 2008 May 8 |
|
| Improved tricyclic inhibitors of trypanothione reductase by screening and chemical synthesis. | 2009 Aug |
Patents
Sample Use Guides
Studies in Rhesus monkeys showed that acute and chronic treatment with GBR12935 (3 mg/kg) decreases on-going cocaine self-administration behavior
Route of Administration:
Intramuscular
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76778-22-8
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64093
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GBR-12935
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9J9974WIBA
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DTXSID2043743
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3456
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ACTIVE MOIETY
