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

• ChemBase ID: 178615
• Molecular Formular: C20H26ClNO2S2
• Molecular Mass: 412.00894
• Monoisotopic Mass: 411.10934876
• SMILES: C(=C\CCN1C[C@H](CCC1)C(=O)O)(\c1c(ccs1)C)/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-;/m0./s1
• InChIKey: YUKARLAABCGMCN-NTISSMGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride
• IUPAC Traditional name: (3S)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride
• Synonyms: (3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic Acid Hydrochloride; Gabitril; Tiagabine Hydrochloride

Database IDs

• CAS Number: 145821-59-6
• PubChem SID: 164234525
• PubChem CID: 11292826

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: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >192°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T436400

A GABA uptake inhibitor. Anticonvulsant.

REFERENCES

• Andersen, K.E., et al.: J. Med. Chem., 36, 1716 (1993)
• Fangold, C.L., et al.: Exp. Neurology, 126, 225 (1993)
• Bauer, J., et al.: J. Epilepsy, 8, 83 (1993)