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G9659

Sigma-Aldrich

GBR 12935 dihydrochloride

≥98% (TLC), powder

Synonyme(s) :

1-[2-(Diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride

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About This Item

Formule empirique (notation de Hill):
C28H34N2O · 2HCl
Numéro CAS:
67469-81-2
Poids moléculaire :
487.50
Numéro MDL:
MFCD00083175
Code UNSPSC :
12352202
ID de substance PubChem :
24277959
Nomenclature NACRES :
NA.77

Pureté

≥98% (TLC)

Forme

powder

Couleur

white

Solubilité

H2O: 20 mg/mL (with warming)

Chaîne SMILES 

Cl[H].Cl[H].C(CN1CCN(CCOC(c2ccccc2)c3ccccc3)CC1)Cc4ccccc4

InChI

1S/C28H34N2O.2ClH/c1-4-11-25(12-5-1)13-10-18-29-19-21-30(22-20-29)23-24-31-28(26-14-6-2-7-15-26)27-16-8-3-9-17-27;;/h1-9,11-12,14-17,28H,10,13,18-24H2;2*1H

Clé InChI

NQWRSILGEXNJIT-UHFFFAOYSA-N

Application

GBR 12935 dihydrochloride has been used as a dopamine reuptake inhibitor to study its effects on noradrenergic stimulation in the medial prefrontal cortex of rats (mPFC). It has also been used as a selective dopamine transporter (DAT) inhibitor to study its effects on behavior and neurochemical response in enriched condition (EC) and impoverished condition (IC) rats.

Actions biochimiques/physiologiques

GBR 12935 inhibits the dopamine and norepinephrine transporters with Kis of 21.5 nM and 225 nM, respectively. It does not inhibit the serotonin transporter (Ki = 6.5 mM). GBR 12935 binds to a nondopaminergic piperazine site in blood platelets and brain that has been identified as cytochrome P450.

Caractéristiques et avantages

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.

Code de la classe de stockage

13 - Non Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

T Hiroi et al.
Biochemical pharmacology, 53(12), 1937-1939 (1997-06-15)
The binding of [3H]1-[2-(diphenylmethoxy)ethyl]-4-(3-phenyl propyl) piperazine (GBR-12935), an antagonist of the dopamine transporter, to human P450s expressed in yeast cells was investigated. Among the ten forms of human P450 tested (CYP1A1, 1A2, 2A6, 2B6, 2C8, 2C9, 2C18, 2D6, 2E1, and
P Allard et al.
Journal of neurochemistry, 62(1), 342-348 (1994-01-01)
The presence of multiple [3H]GBR-12935 binding sites in the human brain has been revealed in several recent studies. One site represents the dopamine uptake site. In rat brain it was demonstrated that [3H]GBR-12935 also binds to nondopaminergic "piperazine acceptor sites."
I Gordon et al.
Life sciences, 55(3), 189-199 (1994-01-01)
It remains controversial whether blood platelet can be used as a peripheral model for the central presynaptic dopaminergic neurons. We investigated the existence of dopamine transport complex in human blood platelet membranes using the selective dopamine uptake inhibitor [3H]GBR 12935
Rita Gálosi et al.
Behavioural brain research, 344, 57-64 (2018-02-18)
Effects of destroyed noradrenergic (NE) innervation in the medial prefrontal cortex (mPFC) were examined on dopamine (DA) content and metabolism. Six-hydroxy-DOPA (6-OHDOPA) or 6-hydroxy-dopamine (6-OHDA) in combination with a potent DA reuptake inhibitor GBR 12935 or 6-OHDA were injected bilaterally
Jun Zhu et al.
Behavioural brain research, 148(1-2), 107-117 (2003-12-20)
Rats raised in an enriched condition (EC) during development display increased hyperactivity to the effect of acute amphetamine compared to rats raised in an impoverished condition (IC). The present study determined whether environmental enrichment differentially alters the effects of GBR
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