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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
Structure of GBR-12935

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

HIDE SMILES / InChI

Molecular Formula C28H34N2O
Molecular Weight 414.5824
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.7 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
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
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
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
Application of the DAT-specific blocker GBR 12,935 produced a significant enhancement in LTP of Schaffer collateral synapses in the CA1 at concentrations as low as 100 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:03:54 UTC 2023
Edited
by admin
on Sat Dec 16 08:03:54 UTC 2023
Record UNII
9J9974WIBA
Record Status Validated (UNII)
Record Version
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Name Type Language
GBR-12935
Common Name English
J227.604F
Code English
GBR 12935
Common Name English
1-HYDROCINNAMYL-4-(2-(DIPHENYLMETHOXY)ETHYL)PIPERAZINE
Systematic Name English
PIPERAZINE, 1-(2-(DIPHENYLMETHOXY)ETHYL)-4-(3-PHENYLPROPYL)-
Systematic Name English
1-(2-(DIPHENYLMETHOXY)ETHYL)-4-(3-PHENYLPROPYL)PIPERAZINE
Systematic Name English
Code System Code Type Description
CAS
76778-22-8
Created by admin on Sat Dec 16 08:03:54 UTC 2023 , Edited by admin on Sat Dec 16 08:03:54 UTC 2023
PRIMARY
CHEBI
64093
Created by admin on Sat Dec 16 08:03:54 UTC 2023 , Edited by admin on Sat Dec 16 08:03:54 UTC 2023
PRIMARY
WIKIPEDIA
GBR-12935
Created by admin on Sat Dec 16 08:03:54 UTC 2023 , Edited by admin on Sat Dec 16 08:03:54 UTC 2023
PRIMARY
FDA UNII
9J9974WIBA
Created by admin on Sat Dec 16 08:03:54 UTC 2023 , Edited by admin on Sat Dec 16 08:03:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID2043743
Created by admin on Sat Dec 16 08:03:54 UTC 2023 , Edited by admin on Sat Dec 16 08:03:54 UTC 2023
PRIMARY
PUBCHEM
3456
Created by admin on Sat Dec 16 08:03:54 UTC 2023 , Edited by admin on Sat Dec 16 08:03:54 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY