| Identification | Back Directory | [Name]
Vanoxerine dihydrochloride | [CAS]
67469-78-7 | [Synonyms]
I-893
GBR 12909
Vanoxerine
Boxeprazine
GBR129092HCl
Vanoxerine 2HCl
vanoxerine-GBR-12909
I893 dihydrochloride
GBR 12909 DIHYDROCHLORIDE
GBR 12909 (hydrochloride)
VANOXERINE DIHYDROCHLORIDE
Vanoxerine 2HCl (GBR-12909)
Vanoxerine Dihydrochloride (GBR-12909)
GBR-12909 DIHYDROCHLORIDE SELECTIVE DOPA MINE UP
1-(3-Phenylpropyl)-4-[2-[bis(4-fluorophenyl)methoxy]ethyl]piperazine
1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
1-(2-BIS-((4-FLUOROPHENYL)METHOXY)ETHYL)-4-(3-PHENYL-2-PROPYL)PIPERAZINE HCL
1-(2-[BIS(4-FLUOROPHENYL) METHOXY]ETHYL)-4-(3-PHENYLPROPYL) PIPERAZINE DIHYDROC
1-[2-[BIS(4-FLUOROPHENYL)METHOXY]ETHYL]-4-[3-PHENYLPROPYL]PIPERAZINE DIHYDROCHLORIDE
1-(2-BIS-[4-FLUOROPHENYL]-METHOXYETHYL)-4-(3-PHENYL-2-PROPYL)PIPERAZINE HYDROCHLORIDE
Piperazine,1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)-, hydrochloride(1:2) | [Molecular Formula]
C28H34Cl2F2N2O | [MDL Number]
MFCD00055193 | [MOL File]
67469-78-7.mol | [Molecular Weight]
523.49 |
| Chemical Properties | Back Directory | [Melting point ]
221 °C | [storage temp. ]
Desiccate at RT | [solubility ]
DMSO: >5 mg/mL Solutions freshly prepared daily
| [form ]
solid
| [color ]
white
| [Water Solubility ]
Soluble in DMSO to 50mM. Soluble to 5mM in water with warming. | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month. |
| Hazard Information | Back Directory | [Uses]
Antidepressant;Dopamine reuptake inhibitor | [Hazard]
A poison. | [Biological Activity]
Potent, competitive inhibitor of dopamine uptake (K i = 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 (IC 50 = 48 nM). Centrally active following systemic administration. | [Description]
GBR 12909 is a potent inhibitor that blocks dopamine uptake (IC50 = 1-51 nM).1,2 It is more than 100-fold less effective at blocking serotonin or noradrenaline uptake.1,2 GBR 12909 effectively inhibits dopamine uptake in vivo, leading to consequent stimulation of dopamine receptors.1,3 GBR 12909 also inhibits pyrilamine binding to the histamine H1 receptor (IC50 = 18 nM) but poorly inhibits ligand binding to dopamine, adrenergic, acetylcholine, serotonin, and γ-aminobutyric acid receptors.2 It also blocks ligand binding to sigma receptors in rat brain (IC50 = 48 nM).4 | [Definition]
ChEBI: Vanoxerine dihydrochloride is a hydrochloride salt that is obtained by reaction of vanoxerine with two equivalents of hydrogen chloride. 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. It has a role as a dopamine uptake inhibitor. It contains a vanoxerine(2+). | [General Description]
Vanoxerine dihydrochloride is a potent inhibitor of dopamine active transporter (DAT, Ki = 1 nM, IC50 = 40 and 51 nM) with >100 fold selectivity over noradrenalin and 5-HT re-uptake transporter. Shown to produce behavioral profile in mice for bipolar mania disease model and ADHD disease models. | [Biochem/physiol Actions]
Highly selective dopamine reuptake inhibitor with behavioral effects similar to cocaine. | [storage]
Room temperature (desiccate) | [References]
1) Andersen?et al. (1989),?The dopamine inhibitor GBR 12909: selectivity and molecular mechanism of action; Eur. J. Pharmacol.,?166?493
2) Contreras?et al. (1990),?GBR-12909 and fluspirilene potently inhibited binding of [3H] (+)3-PPP to sigma receptors in rat brain; Life Sci.,?47?PL133
3) Yorgason?et al. (2011),?Low and high affinity dopamine transporter inhibitors block dopamine uptake within 5 sec of intravenous injection; Neuroscience,?182?125 |
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