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CAS No 115103-54-3 , (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic
acid Search by region : Canada

  • Name: (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic
    acid
  • Synonyms: Tiagabine (INN); Tiagabine [INN:BAN]; Tiagabina; Tiagabine [INN]; Tiagabina [INN-Spanish];(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic
    acid;Tiagabinum [INN-Latin]; Tiagabinum; 115103-54-3;
  • CAS Registry Number:
  • Melting Point: 192oC dec.
  • Density: 1.208 g/cm3
  • Refractive index: 1.604
  • Safety Statements: 26-37/39
  • Hazard Symbols: Xi: Irritant;
  • Molecular Weight: 375.548
  • InchiKey: PBJUNZJWGZTSKL-MRXNPFEDSA-N
  • InChI: InChI=1S/C20H25NO2S2/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)/t16-/m1/s1
  • Risk Statements: 36/37/38
  • Molecular Formula: C20H25NO2S2
  • Molecular Structure:CAS No:115103-54-3 (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic<br />acid

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115103-54-3 TIAGABINE HCL

  • Canada Synth?se AptoChem Inc. [Manufacturer]
  • Tel: 514-496-4252
  • Fax: 514-496-4253
  • Address: Synth?se AptoChem Inc.
    6100 Royalmount Ave
    Montreal, QC
    Canada
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References of (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic
acid
Title: Tiagabine
CAS Registry Number: 115103-54-3
CAS Name: (3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid
Synonyms: (-)-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid; TGB
Manufacturers' Codes: NO-328; NO-05-0328; NNC-05-0328; A-70569
Molecular Formula: C20H25NO2S2
Molecular Weight: 375.55
Percent Composition: C 63.96%, H 6.71%, N 3.73%, O 8.52%, S 17.08%
Literature References: GABA uptake inhibitor. Prepn: F. C. Groenvald, C. Braestrup, WO 8700171 (1987 to Novo); F. C. Gronvald, C. Braestrup, US 5010090 (1991 to Novo Nordisk); K. E. Andersen et al., J. Med. Chem. 36, 1716 (1993). Pharmacology: C. L. Faingold et al., Exp. Neurol. 126, 225 (1994). HPLC determn in human plasma: L. E. Gustavson, S. Chu, J. Chromatogr. 574, 313 (1992). Clinical evaluation as add-on therapy: J. Bauer et al., J. Epilepsy 8, 83 (1995). Review of pharmacology: W. J. Giardina, ibid. 7, 161-166 (1994); and chemistry: H. Mengel, Epilepsia 35, Suppl. 5, S81-S84 (1994). Review of clinical experience: J. P. Leach, M. J. Brodie, Lancet 351, 203 (1998).
 
Derivative Type: Hydrochloride
CAS Registry Number: 145821-59-6
Trademarks: Gabitril (Novo Nordisk)
Molecular Formula: C20H25NO2S2.HCl
Molecular Weight: 412.01
Percent Composition: C 58.30%, H 6.36%, N 3.40%, O 7.77%, S 15.57%, Cl 8.60%
Properties: White to off-white, odorless crystalline powder, mp 192° (dec) (Mengel). [a]D20 -11°. pKa1 3.3; pKa2 9.4. Partition coefficient (octanol/water): 39.3 (pH 7.4). Soly in water: 3%. Practically insol in hexane.
Melting point: mp 192° (dec) (Mengel)
pKa: pKa1 3.3; pKa2 9.4
Optical Rotation: [a]D20 -11°
Log P: Partition coefficient (octanol/water): 39.3 (pH 7.4)
 
Therap-Cat: Anticonvulsant.
Keywords: Anticonvulsant.