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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

Description

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.

CNS Activity

Originator

Gist-Brocades
3
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 3.7 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Diagnostic
Not Provided
504
Unknown

Approved Use

Unknown
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
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
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
Presynaptic control of striatal dopamine neurotransmission in adult vesicular monoamine transporter 2 (VMAT2) mutant mice.
2003 May
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

Patents

EP1568770A2
1
WO2002022801A9
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 GMT 2023
Edited
by admin
on Sat Dec 16 08:03:54 GMT 2023
Record UNII
9J9974WIBA
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Sat Dec 16 08:03:54 GMT 2023
PRIMARY
CHEBI
64093
Created by admin on Sat Dec 16 08:03:54 GMT 2023 , Edited by admin on Sat Dec 16 08:03:54 GMT 2023
PRIMARY
WIKIPEDIA
GBR-12935
Created by admin on Sat Dec 16 08:03:54 GMT 2023 , Edited by admin on Sat Dec 16 08:03:54 GMT 2023
PRIMARY
FDA UNII
9J9974WIBA
Created by admin on Sat Dec 16 08:03:54 GMT 2023 , Edited by admin on Sat Dec 16 08:03:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID2043743
Created by admin on Sat Dec 16 08:03:54 GMT 2023 , Edited by admin on Sat Dec 16 08:03:54 GMT 2023
PRIMARY
PUBCHEM
3456
Created by admin on Sat Dec 16 08:03:54 GMT 2023 , Edited by admin on Sat Dec 16 08:03:54 GMT 2023
PRIMARY
Related Record Type Details
Structure of GBR-12935
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