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Merck

D052

GBR 12909 dihydrochloride

≥98% (HPLC), dopamine transportef nhibitor, solid

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
UNSPSC Code:
12352200
PubChem Substance ID:
24277909
NACRES:
NA.77
MDL number:
MFCD00055193
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
desiccated

Key Documents

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Product Name

GBR 12909 dihydrochloride, solid, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

white

solubility

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

Quality Level

100

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

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000466782
0000466782
0000466068
0000466068
0000342621

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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
Differential Reinforcing Effects of Cocaine and GBR-12909: Biochemical Evidence for Divergent Neuroadaptive Changes in the Mesolimbic Dopaminergic System
Srihari R T, et al.
The Journal of Neuroscience, 16(23), 7416 ?7427-7416 ?7427 (1996)
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.
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
Andrew J D Nelson et al.
The international journal of neuropsychopharmacology, 15(4), 485-496 (2011-05-12)
There is good evidence that forebrain serotonergic systems modulate cognitive flexibility. Latent inhibition (LI) is a cross-species phenomenon which manifests as poor conditioning to a stimulus that has previously been experienced without consequence and is widely considered an index of
View All Related Papers

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