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Merck
CN

S9066

SKF-89976A

>98% (HPLC), solid

Synonym(s):

1-(4,4-Diphenyl-3-butenyl)-3-piperidinecarboxylic acid hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H25NO2 · HCl
CAS Number:
85375-15-1
Molecular Weight:
371.90
NACRES:
NA.77
PubChem Substance ID:
24278796
UNSPSC Code:
12352200
MDL number:
MFCD01321071

Key Documents

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InChI key

SNGGBKYQZVAQKA-UHFFFAOYSA-N

SMILES string

Cl[H].OC(=O)C1CCCN(CC\C=C(/c2ccccc2)c3ccccc3)C1

InChI

1S/C22H25NO2.ClH/c24-22(25)20-13-7-15-23(17-20)16-8-14-21(18-9-3-1-4-10-18)19-11-5-2-6-12-19;/h1-6,9-12,14,20H,7-8,13,15-17H2,(H,24,25);1H

assay

>98% (HPLC)

form

solid

color

white

solubility

DMSO: soluble 20 mg/mL, H2O: insoluble

originator

GlaxoSmithKline

storage temp.

2-8°C

Gene Information

human ... SLC6A1(6529), SLC6A11(6538), SLC6A12(6539)
rat ... Slc6a1(79212), Slc6a12(50676)

Application

SKF-89976A was used to study the role of adenosine receptors in uptake of GABA transport.4,5

Biochem/physiol Actions

GABA transporter type 1 (GAT-1) inhibitor that crosses the blood brain barrier.
SKF-89976A contains a cyclic amino acid with lipophilic moiety that enables the compound to cross the blood-brain barrier.1,2 It decreases the excitotoxic swelling of chick retina cells by blocking the glutamate-induced GABA release.3

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, 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)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
016K46072
016K46071
016K4607
082K4605

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Anniina Alakuijala et al.
The European journal of neuroscience, 23(2), 514-520 (2006-01-20)
Both gamma-aminobutyric acid (GABA)(C) receptor subunit mRNA and protein are expressed in the stratum pyramidale in the CA1 area of the adult rat hippocampus, but so far no conclusive evidence about functional hippocampal GABA(C) receptors has been presented. Here, the
K E Andersen et al.
Journal of medicinal chemistry, 36(12), 1716-1725 (1993-06-11)
A series of different synthetic approaches to novel GABA uptake inhibitors are described, leading to examples which are derivatives of nipecotic acid and guvacine, substituted at nitrogen by 4,4-diaryl-3-butenyl or 2-(diphenylmethoxy)ethyl moieties. The in vitro value for inhibition of [3H]-GABA
Adriana Galvan et al.
Journal of neurophysiology, 94(2), 990-1000 (2005-04-15)
Neurons in the external and internal segment of the globus pallidus (GPe and GPi, respectively) receive substantial GABAergic inputs from the striatum and through axon collaterals of neighboring pallidal neurons. The effects of GABA on pallidal activity depend on the
David J Rossi et al.
The Journal of physiology, 548(Pt 1), 97-110 (2003-02-18)
Cerebellar granule cells are inhibited phasically by GABA released synaptically from Golgi cells, but are inhibited more powerfully by tonic activity of high affinity alpha 6 subunit-containing GABAA receptors. During development the tonic activity is generated by the accumulation of
Christopher B Ransom et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(22), 7672-7684 (2010-06-04)
Ambient GABA in the brain activates GABA(A) receptors to produce tonic inhibition. Membrane potential influences both GABA transport and GABA(A) receptors and could thereby regulate tonic inhibition. We investigated the voltage dependence of tonic currents in cultured rat hippocampal neurons
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