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S9066

Sigma-Aldrich

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
MDL number:
MFCD01321071
UNSPSC Code:
12352200
PubChem Substance ID:
24278796
NACRES:
NA.77

Assay

>98% (HPLC)

form

solid

color

white

solubility

DMSO: soluble 20 mg/mL
H2O: insoluble

originator

GlaxoSmithKline

storage temp.

2-8°C

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

InChI key

SNGGBKYQZVAQKA-UHFFFAOYSA-N

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

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
GABA transporter type 1 (GAT-1) inhibitor that crosses the blood brain barrier.

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 Code

11 - 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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Annalisa Scimemi et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 25(43), 10016-10024 (2005-10-28)
Persistent activation of GABAA receptors by extracellular GABA (tonic inhibition) plays a critical role in signal processing and network excitability in the brain. In hippocampal principal cells, tonic inhibition has been reported to be mediated by alpha5-subunit-containing GABAA receptors (alpha5GABAARs).
Andrea Soragna et al.
The Journal of physiology, 562(Pt 2), 333-345 (2004-10-30)
The relations between apparent affinity for substrates and operating rates have been investigated by two-electrode voltage clamp in the GABA transporter rGAT1 expressed in Xenopus oocytes. We have measured the transport current induced by the presence of GABA, as well
G D Zeevalk et al.
Molecular and chemical neuropathology, 29(1), 27-36 (1996-09-01)
Acute excitotoxicity in the chick retina is characterized by cellular swelling and the subsequent selective release of GABA. In order to understand the source of GABA release, embryonic day 15 retina were incubated with 1 mM glutamate for 30 min
Marcelo D Rosato-Siri et al.
The European journal of neuroscience, 20(10), 2697-2710 (2004-11-19)
For a short time during development immature circuits in the spinal cord and other parts of the central nervous system spontaneously generate synchronous patterns of rhythmic activity. In the case of the spinal cord, it is still unclear how strongly
Marco Milanese et al.
Journal of neurochemistry, 113(2), 489-501 (2010-02-06)
The effect of GABA on glutamate release from astrocytes has been studied in healthy mice and in a murine transgenic model of amyotrophic lateral sclerosis (ALS), using mouse spinal cord gliosomes labeled with [(3)H]d-aspartate ([(3)H]d-ASP). GABA concentration-dependently evoked the release
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