WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 531328
CAS#: 67469-78-7 (HCl)
Description: Vanoxerine, also known as GBR 12909, is a potent inhibitor that blocks dopamine uptake (IC50 = 1-51 nM). GBR 12909 effectively inhibits dopamine uptake in vivo. GBR-12909 binds to the target site on the dopamine transporter (DAT) ~ 50 times more strongly than cocaine, but simultaneously inhibits the release of dopamine. This combined effect only slightly elevates dopamine levels, giving vanoxerine only mild stimulant effects.[2] Vanoxerine has also been observed to be a potent blocker of the IKr (hERG) channel. GBR-12909 also binds with nanomolar affinity to the serotonin transporter.
MedKoo Cat#: 531328
Name: Vanoxerine HCl
CAS#: 67469-78-7 (HCl)
Chemical Formula: C28H34Cl2F2N2O
Exact Mass: 522.2016
Molecular Weight: 523.4898
Elemental Analysis: C, 64.24; H, 6.55; Cl, 13.54; F, 7.26; N, 5.35; O, 3.06
Related CAS #: 67469-69-9 (free base) 67469-78-7 (HCl)
Synonym: Vanoxerine dihydrochloride; GBR 12909; GBR-12909; GBR12909.
IUPAC/Chemical Name: 1-(2-[bis(4-Fluorophenyl)methoxy]ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride
InChi Key: MIBSKSYCRFWIRU-UHFFFAOYSA-N
InChi Code: InChI=1S/C28H32F2N2O.2ClH/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;2*1H
SMILES Code: FC1=CC=C(C(C2=CC=C(F)C=C2)OCCN3CCN(CCCC4=CC=CC=C4)CC3)C=C1.[H]Cl.[H]Cl
Appearance: White to off-white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 523.4898 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Lane EL, Cheetham S, Jenner P. Dopamine uptake inhibitor-induced rotation in 6-hydroxydopamine-lesioned rats involves both D1 and D2 receptors but is modulated through 5-hydroxytryptamine and noradrenaline receptors. J Pharmacol Exp Ther. 2005 Mar;312(3):1124-31. PubMed PMID: 15542624.
2: Mike A, Karoly R, Vizi ES, Kiss JP. A novel modulatory mechanism of sodium currents: frequency-dependence without state-dependent binding. Neuroscience. 2004;125(4):1019-28. PubMed PMID: 15120861.
3: Choong KC, Shen RY. Methylphenidate restores ventral tegmental area dopamine neuron activity in prenatal ethanol-exposed rats by augmenting dopamine neurotransmission. J Pharmacol Exp Ther. 2004 May;309(2):444-51. PubMed PMID: 14724217.
4: Rahman S, Engleman E, Simon J, McBride WJ. Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens. Eur J Pharmacol. 2001 Feb 23;414(1):37-44. PubMed PMID: 11230993.
5: Romualdi P, D'Addario C, Ferri S, Cox BM, Izenwasser S. Chronic GBR 12909 administration differentially alters prodynorphin gene expression compared to cocaine. Eur J Pharmacol. 2001 Feb 16;413(2-3):207-12. PubMed PMID: 11226394.
6: Howell LL, Czoty PW, Kuhar MJ, Carrol FI. Comparative behavioral pharmacology of cocaine and the selective dopamine uptake inhibitor RTI-113 in the squirrel monkey. J Pharmacol Exp Ther. 2000 Feb;292(2):521-9. PubMed PMID: 10640288.
7: Mochizuki T, Villemagne VL, Scheffel U, Liu X, Musachio JL, Dannals RF, Wagner HN Jr. A simple probe measures the pharmacokinetics of[125I]RTI-55 in mouse brain in vivo. Eur J Pharmacol. 1997 Oct 29;338(1):17-23. PubMed PMID: 9407999.
8: Nagase T, Hotta K, Morita S, Sakai K, Yamane M, Omote M, Mizusawa H. [Pharmacological effects of the novel dopamine uptake inhibitor 1-[2-[bis(4-fluorophenyl)-methoxy]ethyl]-4-(3-phenylpropyl) piperazine dihydrochloride (I-893) on the central nervous system]. Nihon Yakurigaku Zasshi. 1991 Aug;98(2):121-41. Japanese. PubMed PMID: 1833294.
9: Mount H, Boksa P, Chaudieu I, Quirion R. Phencyclidine and related compounds evoked [3H]dopamine release from rat mesencephalic cell cultures by a mechanism independent of the phencyclidine receptor, sigma binding site, or dopamine uptake site. Can J Physiol Pharmacol. 1990 Sep;68(9):1200-6. PubMed PMID: 1980428.
10: Nagase T, Ishiko J, Takaori S. [Effects of 1-[2-[bis(fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl) piperazine dihydrochloride (I-893) on turnover of dopamine and norepinephrine in the brain]. Nihon Yakurigaku Zasshi. 1987 Aug;90(2):105-14. Japanese. PubMed PMID: 3119439.
