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Merck
CN

SML0035

Tiagabine hydrochloride

≥98% (HPLC)

Synonym(s):

(-)-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride, (3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidinecarboxylic acid hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C20H25NO2S2 · HCl
CAS Number:
145821-59-6
Molecular Weight:
412.01
NACRES:
NA.77
PubChem Substance ID:
329825105
UNSPSC Code:
12352200
MDL number:
MFCD07369025

Key Documents

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Product Name

Tiagabine hydrochloride, ≥98% (HPLC)

InChI

1S/C20H25NO2S2.ClH/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23;/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23);1H/t16-;/m1./s1

SMILES string

Cl.Cc1ccsc1C(=CCCN2CCC[C@H](C2)C(O)=O)c3sccc3C

InChI key

YUKARLAABCGMCN-PKLMIRHRSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -9 to -12°, c = 1 in H2O

color

white to beige

solubility

H2O: 10 mg/mL, clear

originator

Cephalon

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... SLC6A1(6529)

Related Categories

Application

Tiagabine hydrochloride was used to study serotoninergic transmission in G1 cells. It has also been used to study its anti-aging effects on the sensory neurons of C. elegans.

Biochem/physiol Actions

Selective inhibitor of the synaptic GABA transporter GAT1; Anticonvulsant
Tiagabine hydrochloride is an anticonvulsant and selective GABA reuptake inhibitor through inhibition of the synaptic GABA transporter GAT1.
Tiagabine increases the synaptic GABA and enhances the neuronal inhibition. It is effective as adjunctive treatment of epilepsy and anxiety disorders.

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 is featured on the GABA Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Cephalon. 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

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Certificates of Analysis (COA)

Lot/Batch Number
0000190751
0000190750
0000194395
0000190751
0000190750

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An automated compound screening for anti-aging effects on the function of C. elegans sensory neurons
Bazopoulou D, et al.
Scientific Reports (2017)
Gang Zhao et al.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology, 19(10), 749-758 (2009-07-07)
Safflower, the dry flower of Carthamus tinctorius L., has long been applied for empirically treating cerebral ischemia and depression in traditional Chinese medicine. Pathogenesis of major depression involves monoaminergic transmission. The present study assessed whether safflower or its isolate would
Andrea Eugenio Cavanna et al.
Discovery medicine, 9(45), 138-144 (2010-03-03)
Anti-epileptic drugs (AEDs) have a variety of mechanisms of action which are reflected through different anticonvulsant activities and behavioral effects. Two categories of AEDs are considered based on psychotropic profile. The first group is characterized by potentiation of gamma-aminobutyric acid
Jens V Andersen et al.
Glia, 68(12), 2601-2612 (2020-06-26)
Synaptic transmission is closely linked to brain energy and neurotransmitter metabolism. However, the extent of brain metabolism of the inhibitory neurotransmitter γ-aminobutyric acid (GABA), and the relative metabolic contributions of neurons and astrocytes, are yet unknown. The present study was

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