vanoxerine   Click here for help

GtoPdb Ligand ID: 9983

Synonyms: GBR 12909 | GBR-12909 | GBR12909
Compound class: Synthetic organic
Comment: Competitive inhibitor of dopamine uptake, binds to the target site on the dopamine transporter (DAT). Also a potent sigma receptor ligand.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 10
Topological polar surface area 15.71
Molecular weight 450.25
XLogP 5.35
No. Lipinski's rules broken 1
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Canonical SMILES Fc1ccc(cc1)C(c1ccc(cc1)F)OCCN1CCN(CC1)CCCc1ccccc1
Isomeric SMILES Fc1ccc(cc1)C(c1ccc(cc1)F)OCCN1CCN(CC1)CCCc1ccccc1
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
1. Andersen PH. (1989)
The dopamine inhibitor GBR 12909: selectivity and molecular mechanism of action.
Eur J Pharmacol, 166 (3): 493-504. [PMID:2530094]
2. Contreras PC, Bremer ME, Rao TS. (1990)
GBR-12909 and fluspirilene potently inhibited binding of [3H] (+)3-PPP to sigma receptors in rat brain.
Life Sci, 47 (22): PL133-7. [PMID:1980329]
3. Heikkila RE, Manzino L. (1984)
Behavioral properties of GBR 12909, GBR 13069 and GBR 13098: specific inhibitors of dopamine uptake.
Eur J Pharmacol, 103 (3-4): 241-8. [PMID:6237922]
4. Melia KF, Spealman RD. (1991)
Pharmacological characterization of the discriminative-stimulus effects of GBR 12909.
J Pharmacol Exp Ther, 258 (2): 626-32. [PMID:1678014]