1-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylicacidhydrochloride；SKF89976AHCl

Modify Date: 2025-08-22 22:36:55

1-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylicacidhydrochloride；SKF89976AHCl structure	Common Name	1-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylicacidhydrochloride；SKF89976AHCl
	CAS Number	85375-15-1	Molecular Weight	371.90000
	Density	N/A	Boiling Point	531.4ºC at 760 mmHg
	Molecular Formula	C₂₂H₂₆ClNO₂	Melting Point	N/A
	MSDS	USA	Flash Point	275.2ºC

Use of 1-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylicacidhydrochloride；SKF89976AHCl

SKF89976A hydrochloride is a selective GABA transporter (GAT-1) inhibitor with IC50s of 0.28 μM, 137.34 μM and 202.8 μM for GAT-1, GAT-2 and GAT-3 in CHO cells, respectively.

Name	1-(4,4-diphenylbut-3-enyl)piperidine-3-carboxylic acid,hydrochloride
Synonym	More Synonyms

Description	SKF89976A hydrochloride is a selective GABA transporter (GAT-1) inhibitor with IC50s of 0.28 μM, 137.34 μM and 202.8 μM for GAT-1, GAT-2 and GAT-3 in CHO cells, respectively.
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor Signaling Pathways >> Neuronal Signaling >> GABA Receptor Research Areas >> Neurological Disease
Target	IC50: 0.28 μM (GAT-1), 137.34 μM (GAT-2), 202.8 μM (GAT-3)[1]
In Vitro	SKF89976A has a weak antiallodynic action. SKF89976A weakly inhibits serotonin transporter (SERT), noradrenaline transporter (NET), and dopamine transporter (DAT) in chinese hamster ovary (CHO) cells stably expressing each transporter using a substrate uptake assay, with IC50 values of 3514 , 202.13, and 728.8, respectively[1]. SKF89976A is a GABA-transport blocker. GABA (1 mM) elicited an inward current that is completely suppressed by the GABA transport inhibitors tiagabine (10 μM) and SKF89976A (100 μM), but is unaffected by 100 μM picrotoxin. 100 μM SKF 89976-A is known to block the transport of GABA into cells, completely eliminated the GABA-elicited current in a reversible fashion[2]. SKF89976A is a nontransportable blockers of GAT-1. SKF89976-A also suppresses baseline inward currents that likely result from tonic GAT activation by background GABA. SKF89976A (100 μM) reversibly reduces GAT currents in every studied cell by 67.9±4.4% (n=19). Intracellular perfusion of 20 μM SKF89976-A progressively reduced and blocked GABA-induced GAT currents without blocking GABAAR-mediated currents (n=4)[3].
In Vivo	SKF89976A produces a weak antiallodynic response when administered i.v. (0.3 mg/kg). The i.t. injection of SKF89976A dose-dependently ameliorates the reduction in the withdrawal threshold in PSL model mice[1].
Cell Assay	CHO cells stably expressing the mouse GAT subtypes, rat serotonin transporter (SERT), rat noradrenaline transporter (NET), and rat dopamine transporter (DAT) are incubated with 10 nM tritium-labeled GABA or monoamines for 10 min in the absence or presence of various concentrations of the GAT inhibitors (e.g., SKF89976A) tested. Values presented for SERT, NET, and DAT are the mean±S.E.M. for 3 experiments, with each being performed in duplicate[1].
Animal Admin	Mice[1] 5-week-old ddY male mice, weighing 25-30 g at the beginning of the study are used. Mice are administered NNC05-2090, SKF89976A (0.3 mg/kg, i.p.), (S)-SNAP5114, or amitriptyline. The composition of ACSF (in mM) is 142 mM NaCl, 5 mM KCl, 2 mM CaCl2, 2 mM MgCl2, 1.25 mM NaH2PO4, 10 mM d-glucose, 10 mM HEPES, and 0.05% fatty acid-free bovine serum albumin (pH 7.4). The intraperitoneal (i.p.) injection of drugs is administered in a volume of 0.1 mL/10 g body weight. When given intravenously (i.v.), solutions are injected into the tail vein in a volume of 0.1 mL/10 g body weight. The head of a mouse is placed into a plastic cap and the body is held with one hand for an intrathecal (i.t.) injection. A 27-gauge needle attached to a Hamilton microsyringe is inserted into the subarachnoid space between the L5 and L6 vertebrae of the conscious mouse and 5 mL of the drug solution is slowly injected[1].
References	[1]. Jinzenji A, et al. Antiallodynic action of 1-(3-(9H-Carbazol-9-yl)-1-propyl)-4-(2-methyoxyphenyl)-4-piperidinol (NNC05-2090), a betaine/GABA transporter inhibitor. J Pharmacol Sci. 2014;125(2):217-26. [2]. Kreitzer MA, et al. Glutamate modulation of GABA transport in retinal horizontal cells of the skate. J Physiol. 2003 Feb 1;546(Pt 3):717-31. [3]. Barakat L, et al. GAT-1 and reversible GABA transport in Bergmann glia in slices. J Neurophysiol. 2002 Sep;88(3):1407-19.

Boiling Point	531.4ºC at 760 mmHg
Molecular Formula	C₂₂H₂₆ClNO₂
Molecular Weight	371.90000
Flash Point	275.2ºC
Exact Mass	371.16500
PSA	40.54000
LogP	5.04490
InChIKey	SNGGBKYQZVAQKA-UHFFFAOYSA-N
SMILES	Cl.O=C(O)C1CCCN(CCC=C(c2ccccc2)c2ccccc2)C1
Storage condition	2-8℃

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	NONH for all modes of transport
HS Code	2933399090

ethyl N-(4,4-di...

CAS#:85375-14-0

~65%

1-(4,4-diphenyl...

CAS#:85375-15-1

Literature: Ali, Fadia E.; Bondinell, William E.; Dandridge, Penelope A.; Frazee, James S.; Garvey, Eleanor; et al. Journal of Medicinal Chemistry, 1985 , vol. 28, # 5 p. 653 - 660

Precursor 1
CAS#:85375-14-0 ethyl N-(4,4-di...
DownStream 0

HS Code	2933399090
Summary	2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Age-dependent changes in the susceptibility to thiopental anesthesia in mice: analysis of the relationship to the functional expression of GABA transporter.

Pharmacol. Biochem. Behav. 103(2) , 267-72, (2012)

The potency of anesthetics changes during development, probably due not only to pharmacokinetic factors such as differential distribution and/or metabolism, but also to pharmacodynamic factors such as...

Stiripentol, a putative antiepileptic drug, enhances the duration of opening of GABA-A receptor channels.

Epilepsia 47 , 706-716, (2006)

Stiripentol (STP) is currently an efficient drug for add-on therapy in infantile epilepsies because it improves the efficacy of antiepileptic drugs (AEDs) through its potent inhibition of liver cytoch...

Selective gating of glutamatergic inputs to excitatory neurons of amygdala by presynaptic GABAb receptor.

Neuron 61(6) , 917-29, (2009)

GABAb receptor (GABAbR)-mediated suppression of glutamate release is critical for limiting glutamatergic transmission across the central nervous system (CNS). Here we show that, upon tetanic stimulati...

Name: Primary cell-based high-throughput screening assay for identification of compounds th...
Source: Johns Hopkins Ion Channel Center
Target: regulator of G-protein signaling 4 isoform 2 [Homo sapiens]
External Id: JHICC_RGS_Act_HTS

Name: qHTS to identify inhibitors of the New Delhi Metallo-beta-lactamase (NDM): assay vali...
Source: NCGC
External Id: adst_MBL_Abs_LOPAC_o1

Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN

Name: QFRET-based biochemical primary high throughput screening assay to identify exosite i...
Source: The Scripps Research Institute Molecular Screening Center
Target: disintegrin and metalloproteinase domain-containing protein 17 preproprotein [Homo sapiens]
External Id: ADAM17_INH_QFRET_1536_1X%INH PRUN

Name: Inhibition of neurosphere proliferation of mouse neural precursor cells by MTT assay
Source: ChEMBL
Target: N/A
External Id: CHEMBL1266185

Name: In vitro inhibition of [3H]GABA uptake in rat synaptosomes
Source: ChEMBL
Target: N/A
External Id: CHEMBL784482

Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN

Name: uHTS identification of small molecule activators of the adaptive arm of the Unfolded ...
Source: Burnham Center for Chemical Genomics
Target: N/A
External Id: BCCG-A405-UPR-XBP1-PrimaryAgonist-Assay

Name: Rescue cell viability in cybrid cells with a genetic mutation in complex 1 of the mit...
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
Target: N/A
External Id: HMS1315

Name: Fluorescence polarization to screen for inhibitor that competite the binding of FadD2...
Source: Broad Institute
Target: FATTY-ACID-CoA LIGASE FADD28 (FATTY-ACID-CoA SYNTHETASE)
External Id: 2147-01_Inhibitor_SinglePoint_HTS_Activity

Total 144, Current Page 1 of 15

S1589_Selleck

1-(4,4-Diphenylbut-3-en-1-yl)piperidine-3-carboxylic acid hydrochloride (1:1)

1-(4,4-Diphenyl-3-buten-1-yl)-3-piperidinecarboxylic acid hydrochloride (1:1)

3-Piperidinecarboxylic acid, 1-(4,4-diphenyl-3-buten-1-yl)-, hydrochloride (1:1)

SKF 89976A

SKF89976A (hydrochloride)

1-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylicacidhydrochloride；SKF89976AHCl

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.

1-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylicacidhydrochloride；SKF89976AHCl

Use of 1-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylicacidhydrochloride；SKF89976AHCl

Names

Biological Activity

Chemical & Physical Properties

Safety Information

Synthetic Route

Precursor & DownStream

Customs

Articles30

Bioassay

Synonyms

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.