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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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
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
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
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
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