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CHEBI:64089 - vanoxerine

ChEBI IDCHEBI:64089
ChEBI Namevanoxerine
Stars
DefinitionAn N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration.
Last Modified25 February 2016
SubmitterSteve
DownloadsMolfile
FormulaC28H32F2N2O
Net Charge0
Average Mass450.573
Monoisotopic Mass450.24827
SMILESFc1ccc(C(OCCN2CCN(CCCc3ccccc3)CC2)c2ccc(F)cc2)cc1
InChIInChI=1S/C28H32F2N2O/c29-26-12-8-24(9-13-26)28(25-10-14-27(30)15-11-25)33-22-21-32-19-17-31(18-20-32)16-4-7-23-5-2-1-3-6-23/h1-3,5-6,8-15,28H,4,7,16-22H2
InChIKeyNAUWTFJOPJWYOT-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
dopamine uptake inhibitor  A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
Application:
dopamine uptake inhibitor  A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
ChEBI Ontology
Outgoing Relation(s)
vanoxerine (CHEBI:64089) has role dopamine uptake inhibitor (CHEBI:51039)
vanoxerine (CHEBI:64089) is a N-alkylpiperazine (CHEBI:46845)
vanoxerine (CHEBI:64089) is a ether (CHEBI:25698)
vanoxerine (CHEBI:64089) is a organofluorine compound (CHEBI:37143)
vanoxerine (CHEBI:64089) is a tertiary amino compound (CHEBI:50996)
vanoxerine (CHEBI:64089) is conjugate base of vanoxerine(2+) (CHEBI:64087)
Incoming Relation(s)
vanoxerine(2+) (CHEBI:64087) is conjugate acid of vanoxerine (CHEBI:64089)
IUPAC Name 
1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine
INNs  Source
vanoxerinaChemIDplus
vanoxerinumChemIDplus
vanoxerineChemIDplus
Synonyms  Source
GBR12909ChEBI
GBR 12909ChEBI
Manual XrefsDatabases
VanoxerineWikipedia
LSM-2703LINCS
Registry NumbersSources
Reaxys:587912Reaxys
CAS:67469-69-6ChemIDplus
Citations