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Submit ReviewTiagabine hydrochloride
Description: Selective GAT-1 inhibitor; anticonvulsant
Chemical Name: (3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride
Purity: ≥99% (HPLC)
Biological Activity for Tiagabine hydrochloride
Tiagabine hydrochloride is a 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 for Tiagabine hydrochloride
Tiagabine hydrochloride is also offered as part of the Tocriscreen 2.0 Max and Tocriscreen FDA-Approved Drugs. Find out more about compound libraries available from Tocris.
Technical Data for Tiagabine hydrochloride
| 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Tiagabine hydrochloride
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 20.6 | 50 | |
| DMSO | 41.2 | 100 |
Preparing Stock Solutions for Tiagabine hydrochloride
The following data is based on the product molecular weight 412.01. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| 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 for Tiagabine hydrochloride
References for Tiagabine hydrochloride
References are publications that support the biological activity of the product.
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 gabap. in mouse models of acute, prolonged, and chronic nociception. J.Pharmacol.Exp.Ther. 302 1168 PMID: 12183677
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Keywords: Tiagabine hydrochloride, Tiagabine hydrochloride supplier, antiepileptic, anticonvulsants, gaba, transporters, uptake, inhibitors, inhibits, gat-1, selective, antinociception, antinociceptive, GABA, Transporters, 4256, Tocris Bioscience
2 Citations for Tiagabine hydrochloride
Citations are publications that use Tocris products. Selected citations for Tiagabine hydrochloride include:
María Victoria et al (2017) GAT-1 mediated GABA uptake in rat oligodendrocytes. Glia 65 514-522 PMID: 28071826
Sathyanesan (2018) Neonatal brain injury causes cerebellar learning deficits and Purkinje cell dysfunction. Nature Communications 9 3235 PMID: 30104642
Do you know of a great paper that uses Tiagabine hydrochloride from Tocris? Please let us know.
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
GABA Receptors Scientific Review
Written by Ian Martin, Norman Bowery and Susan Dunn, this review provides a history of the GABA receptor, as well as discussing the structure and function of the various subtypes and the clinical potential of receptor modulators; compounds available from Tocris are listed.
Addiction Poster
The key feature of drug addiction is the inability to stop using a drug despite clear evidence of harm. This poster describes the brain circuits associated with addiction, and provides an overview of the main classes of addictive drugs and the neurotransmitter systems that they target.