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D052

GBR 12909 dihydrochloride

Name: GBR 12909 dihydrochloride
Brand: SIGMA

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

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :

C₂₈H₃₂F₂N₂O · 2HCl

Numéro CAS:

67469-78-7

Poids moléculaire :

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

Service technique

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Propriétés

Nom du produit

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)

Description

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.

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Classe de stockage

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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Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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

Insulin in the ventral tegmental area reduces hedonic feeding and suppresses dopamine concentration via increased reuptake.

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.

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

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