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D052

Sigma-Aldrich

GBR 12909 dihydrochloride

solid, ≥98% (HPLC)

Synonym(s):

1-(2-[bis(4-Fluorophenyl)methoxy]ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C28H32F2N2O · 2HCl
CAS Number:
67469-78-7
Molecular Weight:
523.49
MDL number:
MFCD00055193
UNSPSC Code:
12352200
PubChem Substance ID:
24277909
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >5 mg/mL (Solutions freshly prepared daily)

SMILES string

Cl.Cl.Fc1ccc(cc1)C(OCCN2CCN(CCCc3ccccc3)CC2)c4ccc(F)cc4

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

InChI key

MIBSKSYCRFWIRU-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816)

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Application

GBR 12909 dihydrochloride has been used as a dopamine transporter (DAT) inhibitor:

  • to study its effects on LPS-induced mRNA expression on the proinflammatory cytokines in the mouse striatum
  • to study its effects on neurotransmitter release in zebrafish brain
  • in DA uptake assay in mice striatal fraction

Biochem/physiol Actions

GBR 12909 may show pharmacotherapeutic effects against cocaine addiction.
GBR 12909 is a highly selective dopamine reuptake inhibitor with behavioral effects similar to cocaine.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D Matecka et al.
Journal of medicinal chemistry, 39(24), 4704-4716 (1996-11-22)
The design, synthesis, and biological evaluation of compounds related to the dopamine (DA) uptake inhibitors: 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (1) and 1-[2-[bis-(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (2) (GBR 12395 and GBR 12909, respectively), directed toward the development and identification of new ligands interacting with high potency and
Dmitry M Mebel et al.
The European journal of neuroscience, 36(3), 2336-2346 (2012-06-21)
Mesolimbic dopamine (DA) signaling has been implicated in the incentive, reinforcing and motivational aspects of food intake. Insulin receptors are expressed on dopaminergic neurons of the ventral tegmental area (VTA), and insulin may act in the VTA to suppress feeding.
Katherine M Serafine et al.
Pharmacology, biochemistry, and behavior, 102(2), 269-274 (2012-05-15)
Although cocaine readily induces taste aversions, little is known about the mechanisms underlying this effect. It has been suggested that its inhibitory effects at one of the monoamine transporters may be mediating this suppression. Using the cross-drug preexposure preparation, the
Giovanni Hernandez et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(32), 11032-11041 (2012-08-10)
Dopaminergic neurons contribute to intracranial self-stimulation (ICSS) and other reward-seeking behaviors, but it is not yet known where dopaminergic neurons intervene in the neural circuitry underlying reward pursuit or which psychological processes are involved. In rats working for electrical stimulation
P W Czoty et al.
Psychopharmacology, 148(3), 299-306 (2001-02-07)
The behavioral effects of cocaine have been linked to brain dopamine systems. Extending the findings to neurochemical studies in the squirrel monkey would enhance our understanding of the behavioral pharmacology of cocaine in nonhuman primates. The present studies characterized the
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