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G9659

Sigma-Aldrich

GBR 12935 dihydrochloride

≥98% (TLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C28H34N2O · 2HCl
CAS Number:
67469-81-2
Molecular Weight:
487.50
MDL number:
MFCD00083175
UNSPSC Code:
12352202
PubChem Substance ID:
24277959
NACRES:
NA.77

Assay

≥98% (TLC)

form

powder

color

white

solubility

H2O: 20 mg/mL (with warming)

SMILES string

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

InChI key

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.

Biochem/physiol Actions

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.

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

13 - Non 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’.

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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
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
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."
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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