Skip to Content
Merck
CN
All Photos(1)

Key Documents

View All Documentation

Safety Information

S9066

Sigma-Aldrich

SKF-89976A

>98% (HPLC), solid

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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 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

Regulatory Information

新产品

Choose from one of the most recent versions:

Certificates of Analysis (COA)

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

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
Tal Laviv et al.
Neuron, 67(2), 253-267 (2010-07-31)
Presynaptic GABA(B) receptor (GABA(B)R) heterodimers are composed of GB(1a)/GB(2) subunits and critically influence synaptic and cognitive functions. Here, we explored local GABA(B)R activation by integrating optical tools for monitoring receptor conformation and synaptic vesicle release at individual presynaptic boutons of
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service