CHEBI:64089 - vanoxerine

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ChEBI Name vanoxerine
ChEBI ID CHEBI:64089
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C28H32F2N2O
Net Charge 0
Average Mass 450.56330
Monoisotopic Mass 450.24827
InChI InChI=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
InChIKey NAUWTFJOPJWYOT-UHFFFAOYSA-N
SMILES Fc1ccc(cc1)C(OCCN1CCN(CCCc2ccccc2)CC1)c1ccc(F)cc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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(s): 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.
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ChEBI Ontology
Outgoing 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 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 Sources
vanoxerina ChemIDplus
vanoxerine ChemIDplus
vanoxerinum ChemIDplus
Synonyms Sources
GBR 12909 ChEBI
GBR12909 ChEBI
Manual Xrefs Databases
LSM-2703 LINCS
Vanoxerine Wikipedia
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Registry Numbers Types Sources
587912 Reaxys Registry Number Reaxys
67469-69-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
25 February 2016