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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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$284.40
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$753.00
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$1,064.00

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25 MG
$284.40
100 MG
$753.00
250 MG
$1,064.00

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

$284.40

List Price$316.00Save 10%
Web-Only Promotion
Check Cart for Availability
Request a Bulk Order

Quality Level

100

assay

≥98% (HPLC)

form

solid

storage condition

desiccated

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[1]
  • to study its effects on neurotransmitter release in zebrafish brain[2]
  • in DA uptake assay in mice striatal fraction[3]

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.[4]

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_germany

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
0000391193
0000391193
036M4605V
082M4613V
068K4601

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Dopamine inhibits the expression of proinflammatory cytokines of microglial cells through the formation of dopamine quinone in the mouse striatum
Yasuhiro Y, et al.
Journal of Pharmacological Sciences, 41-50 (2022)
Anushka B P Fernando et al.
Psychopharmacology, 219(2), 341-352 (2011-07-16)
Impulsivity is associated with a number of psychiatric disorders, most notably attention deficit/hyperactivity disorder (ADHD). Drugs that augment catecholamine function (e.g. methylphenidate and the selective noradrenaline reuptake inhibitor atomoxetine) have clinical efficacy in ADHD, but their precise mechanism of action
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)
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.
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