Tiagabine hydrochloride

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Cat.No. 4256 - Tiagabine hydrochloride | C20H25NO2S2.HCl | CAS No. 145821-59-6
Description: GABA uptake inhibitor; anticonvulsant
Chemical Name: (3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride
Purity: ≥99% (HPLC)
Datasheet
Citations
Literature

Biological Activity

GABA uptake inhibitor (IC50 = 67 nM in vivo). Exhibits high affinity and selectivity for the GAT-1 GABA transporter. Anticonvulsant; also attenuates established dynorphin-induced allodynia in a mouse model after systemic administration.

Compound Libraries

Tiagabine hydrochloride is also offered as part of the Tocriscreen Plus and Tocriscreen Library of FDA-Approved Compounds. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 412.01
Formula C20H25NO2S2.HCl
Storage Desiccate at RT
Purity ≥99% (HPLC)
CAS Number 145821-59-6
PubChem ID 91274
InChI Key YUKARLAABCGMCN-PKLMIRHRSA-N
Smiles CC3=C(SC=C3)/C(C2=C(C)C=CS2)=C\CCN1C[C@H](C(O)=O)CCC1.Cl

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 41.2 100
water 20.6 50

Preparing Stock Solutions

The following data is based on the product molecular weight 412.01. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.43 mL 12.14 mL 24.27 mL
5 mM 0.49 mL 2.43 mL 4.85 mL
10 mM 0.24 mL 1.21 mL 2.43 mL
50 mM 0.05 mL 0.24 mL 0.49 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Andersen et al (1993) The synthesis of novel GABA uptake inhibitors. 1. Elucidation of the structure-activity studies leading to the choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-butenyl]-3-piperidinecarboxylic acid (tiagabine) as an anticonvulsant drug ca J.Med.Chem. 36 1716 PMID: 8510100

Dhar et al (1994) Design, synthesis and evaluation of substituted triarylnipecotic acid derivatives as GABA updake inhibitors: identification of a ligand with moderate affinity and selectivity for the cloned human GABA transporter GAT-3. J.Med.Chem. 37 2334 PMID: 8057281

Laughlin et al (2002) Comparison of antiepileptic drugs tiagabine, lamotrigine, and gabapentin in mouse models of acute, prolonged, and chronic nociception. J.Pharmacol.Exp.Ther. 302 1168 PMID: 12183677


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Citations for Tiagabine hydrochloride

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