Skip to Content
Merck
All Photos(4)

Key Documents

View All Documentation

D052

Sigma-Aldrich

GBR 12909 dihydrochloride

solid, ≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(4)

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)

Looking for similar products? Visit Product Comparison Guide

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service