(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride

• ChemBase ID: 155065
• Molecular Formular: C20H26ClNO2S2
• Molecular Mass: 412.00894
• Monoisotopic Mass: 411.10934876
• SMILES: Cc1ccsc1/C(=C/CCN1CCC[C@H](C1)C(=O)O)/c1c(ccs1)C.Cl
• Canonical SMILES: OC(=O)[C@@H]1CCCN(C1)CC/C=C(/c1sccc1C)\c1sccc1C.Cl
• InChI: 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
• InChIKey: YUKARLAABCGMCN-PKLMIRHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride
• IUPAC Traditional name: tiagabine hydrochloride
• Synonyms: (-)-(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; Tiagabine hydrochloride

Database IDs

• CAS Number: 145821-59-6
• MDL Number: MFCD07369025
• PubChem SID: 162249203
• PubChem CID: 91274

CALCULATED PROPERTIES

• Acid pKa: 4.1433096
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.5883915
• LogD (pH = 7.4): 2.59872
• Log P: 2.6014485
• Molar Refractivity: 115.3171 cm^3
• Polarizability: 40.297897 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥14 mg/mL
• Apperance: white to tan powder
• Optical Rotation: [α]/D -8.5 to 10°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H25NO2S2 · xHCl

DETAILS

Sigma Aldrich - SML0035

Biochem/physiol Actions
Tiagabine hydrochloride is an anticonvulsant and selective GABA reuptake inhibitor through inhibition of the synaptic GABA transporter GAT1.