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D052

GBR 12909 dihydrochloride

Name: GBR 12909 dihydrochloride
Brand: SIGMA

≥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

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Product Name

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

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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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Modulation of high impulsivity and attentional performance in rats by selective direct and indirect dopaminergic and noradrenergic receptor agonists.

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)

Development of novel, potent, and selective dopamine reuptake inhibitors through alteration of the piperazine ring of 1-[2-(diphenylmethoxy)ethyl]-and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909).

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

Dopamine mediates cocaine-induced conditioned taste aversions as demonstrated with cross-drug preexposure to GBR 12909.

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

Cocaine-induced changes in extracellular dopamine determined by microdialysis in awake squirrel monkeys.

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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Global Trade Item Number

SKU	GTIN
D052-100MG	04061833557754
D052-250MG	04061833557761
D052-25MG	04061833557778

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