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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Maarten Loos et al.
Behavioural brain research, 214(2), 216-224 (2010-06-29)
Among the best-replicated and most heritable endophenotypes of attention-deficit/hyperactivity disorder (ADHD) are deficits in attention, inhibitory response control and larger intra-individual variability in response latencies. Here, we explored the presence of these heritable ADHD endophenotypes in two commonly used inbred
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
Olof Eriksson et al.
Upsala journal of medical sciences, 116(2), 100-106 (2011-03-30)
Occupancy-over-time was determined for two dopamine transporter (DAT) inhibitors through modeling of their ability to displace the PET ligand [(11)C]CIT. The tracer was held at a pseudo steady state in a reference tissue by target controlled infusion. Rhesus monkeys (n
Benjamin A Pawlisch et al.
Brain research, 1353, 113-124 (2010-07-17)
Female songbirds use attributes of male song to select mates. Different types of male song differ in incentive value (or the ability to attract females). Dopamine plays a role in incentive value and reward; however, little is known about its
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)
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