Product Name

  • Name

    Tiagabine

  • EINECS
  • CAS No. 115103-54-3
  • Article Data5
  • CAS DataBase
  • Density 1.208 g/cm3
  • Solubility
  • Melting Point 192 °C
  • Formula C20H25NO2S2
  • Boiling Point 568 °C at 760 mmHg
  • Molecular Weight 375.556
  • Flash Point 297.3 °C
  • Transport Information
  • Appearance white to off-white crystalline solid
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 115103-54-3 (Tiagabine)
  • Hazard Symbols IrritantXi
  • Synonyms 3-Piperidinecarboxylicacid, 1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-, (3R)- (9CI);3-Piperidinecarboxylic acid, 1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-, (R)-;(R)-Tiagabine; Gabatril; NO 050328; NO 328; TGB; Tiagabine
  • PSA 97.02000
  • LogP 5.78470

Synthetic route

ethyl (R)-1-<4,4-bis(3-methyl-2-thienyl)-3-butenyl>-3-piperidinecarboxylate
145821-58-5

ethyl (R)-1-<4,4-bis(3-methyl-2-thienyl)-3-butenyl>-3-piperidinecarboxylate

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
With hydrogenchloride In water90%
With hydrogenchloride In water90%
With hydrogenchloride In water86%
With hydrogenchloride In water86%
With sodium hydroxide In ethanol for 4h; Ambient temperature;
tiagabine hydrochloride

tiagabine hydrochloride

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 20℃; for 3h; Product distribution / selectivity;
With sodium hydroxide In water pH=6; Product distribution / selectivity; Aqueous phosphate buffer; Sonographic reaction; No light exposure;
Stage #1: tiagabine hydrochloride With sodium hydroxide In dichloromethane; water at 20℃; for 1 - 2.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 1 - 2h; Product distribution / selectivity;
2-bromo-3-methylthiophene
14282-76-9

2-bromo-3-methylthiophene

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) Mg / 1.) Et2O, 1 h, 2.) Et2O, 1 h
2: 76 percent / MnO2 / CH2Cl2 / 16 h / Ambient temperature
3: 1.) Mg / 1.) THF, reflux, 0.5 h, 2.) THF, reflux, 1.5 h
4: 46 percent / 48percent aq. HBr / acetic acid / 1.5 h / 10 °C
5: 50 percent / KI, K2CO3 / acetone / 44 h / Ambient temperature
6: 12 M aq. NaOH / ethanol / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 1.) n-BuLi / 1.) Et2O, 10 deg C, 15 min, 2.) Et2O, -70 deg C, 2.5 h
2: 20percent aq. H2SO4 / propan-2-ol / 3 h / Ambient temperature
3: 50 percent / KI, K2CO3 / acetone / 44 h / Ambient temperature
4: 12 M aq. NaOH / ethanol / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1.1: magnesium / tetrahydrofuran / 1 h / 35 °C
1.2: 2 h / 0 °C / Reflux
2.1: hydrogenchloride / water; methanol / 1 °C / Reflux
3.1: triethylamine / diethyl ether / 1 h
4.1: potassium iodide; potassium carbonate / acetone / 120 h / 20 °C
5.1: sodium hydroxide / water; methanol / 2 h / 20 - 50 °C
6.1: hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave
View Scheme
3-methyl-2-thiophenecarboxaldehdye
5834-16-2

3-methyl-2-thiophenecarboxaldehdye

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) Mg / 1.) Et2O, 1 h, 2.) Et2O, 1 h
2: 76 percent / MnO2 / CH2Cl2 / 16 h / Ambient temperature
3: 1.) Mg / 1.) THF, reflux, 0.5 h, 2.) THF, reflux, 1.5 h
4: 46 percent / 48percent aq. HBr / acetic acid / 1.5 h / 10 °C
5: 50 percent / KI, K2CO3 / acetone / 44 h / Ambient temperature
6: 12 M aq. NaOH / ethanol / 4 h / Ambient temperature
View Scheme
bis(3-methyl-2-thienyl)methanone
30717-55-6

bis(3-methyl-2-thienyl)methanone

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) Mg / 1.) THF, reflux, 0.5 h, 2.) THF, reflux, 1.5 h
2: 46 percent / 48percent aq. HBr / acetic acid / 1.5 h / 10 °C
3: 50 percent / KI, K2CO3 / acetone / 44 h / Ambient temperature
4: 12 M aq. NaOH / ethanol / 4 h / Ambient temperature
View Scheme
bis(3-methyl-2-thienyl)methanol
148319-25-9

bis(3-methyl-2-thienyl)methanol

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 76 percent / MnO2 / CH2Cl2 / 16 h / Ambient temperature
2: 1.) Mg / 1.) THF, reflux, 0.5 h, 2.) THF, reflux, 1.5 h
3: 46 percent / 48percent aq. HBr / acetic acid / 1.5 h / 10 °C
4: 50 percent / KI, K2CO3 / acetone / 44 h / Ambient temperature
5: 12 M aq. NaOH / ethanol / 4 h / Ambient temperature
View Scheme
2-[4-bromo-1-(3-methylthien-2-yl)but-1-enyl]-3-methylthiophene
109857-81-0

2-[4-bromo-1-(3-methylthien-2-yl)but-1-enyl]-3-methylthiophene

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / KI, K2CO3 / acetone / 44 h / Ambient temperature
2: 12 M aq. NaOH / ethanol / 4 h / Ambient temperature
View Scheme
cyclopropylbis(3-methyl-2-thienyl)methanol
148319-26-0

cyclopropylbis(3-methyl-2-thienyl)methanol

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 46 percent / 48percent aq. HBr / acetic acid / 1.5 h / 10 °C
2: 50 percent / KI, K2CO3 / acetone / 44 h / Ambient temperature
3: 12 M aq. NaOH / ethanol / 4 h / Ambient temperature
View Scheme
4-Bromo-1,1-bis-(3-methyl-thiophen-2-yl)-butan-1-ol
922184-80-3

4-Bromo-1,1-bis-(3-methyl-thiophen-2-yl)-butan-1-ol

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 20percent aq. H2SO4 / propan-2-ol / 3 h / Ambient temperature
2: 50 percent / KI, K2CO3 / acetone / 44 h / Ambient temperature
3: 12 M aq. NaOH / ethanol / 4 h / Ambient temperature
View Scheme
4,4-bis(3-methyl-2-thienyl)-3-buten-1-ol
847233-27-6

4,4-bis(3-methyl-2-thienyl)-3-buten-1-ol

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / diethyl ether / 1 h
2: potassium iodide; potassium carbonate / acetone / 120 h / 20 °C
3: sodium hydroxide / water; methanol / 2 h / 20 - 50 °C
4: hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave
View Scheme
1-(4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid

1-(4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
With C63H78IrNOP(2+)*C32H12BF24(1-); hydrogen In methanol at 60℃; under 4560.31 Torr; for 12h; Autoclave; enantioselective reaction;n/a
arecoline hydrobromide
300-08-3

arecoline hydrobromide

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate; water / 0.5 h / 20 °C
2: potassium iodide; potassium carbonate / acetone / 120 h / 20 °C
3: sodium hydroxide / water; methanol / 2 h / 20 - 50 °C
4: hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave
View Scheme
1-(1-chloroethyl) 3-methyl 5,6-dihydropyridine-1,3(2H)-dicarboxylate
92600-27-6

1-(1-chloroethyl) 3-methyl 5,6-dihydropyridine-1,3(2H)-dicarboxylate

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: methanol / 2 h / Reflux
1.2: 0.5 h
2.1: potassium iodide; potassium carbonate / acetone / 120 h / 20 °C
3.1: sodium hydroxide / water; methanol / 2 h / 20 - 50 °C
4.1: hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave
View Scheme
norarecoline
495-19-2

norarecoline

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium iodide; potassium carbonate / acetone / 120 h / 20 °C
2: sodium hydroxide / water; methanol / 2 h / 20 - 50 °C
3: hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave
View Scheme
1,1-bis(3-methylthiophen-2-yl)butane-1,4-diol
847233-26-5

1,1-bis(3-methylthiophen-2-yl)butane-1,4-diol

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogenchloride / water; methanol / 1 °C / Reflux
2: triethylamine / diethyl ether / 1 h
3: potassium iodide; potassium carbonate / acetone / 120 h / 20 °C
4: sodium hydroxide / water; methanol / 2 h / 20 - 50 °C
5: hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave
View Scheme
4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl methanesulfonate
847233-13-0

4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl methanesulfonate

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium iodide; potassium carbonate / acetone / 120 h / 20 °C
2: sodium hydroxide / water; methanol / 2 h / 20 - 50 °C
3: hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave
View Scheme
methyl 1-(4,4-bis(3-methylthiophen-2-yl)but-3-en)-1,2,5,6-tetrahydropyridine-3-carboxylate

methyl 1-(4,4-bis(3-methylthiophen-2-yl)but-3-en)-1,2,5,6-tetrahydropyridine-3-carboxylate

tiagabine
115103-54-3

tiagabine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; methanol / 2 h / 20 - 50 °C
2: hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave
View Scheme
tiagabine
115103-54-3

tiagabine

tiagabine hydrobromide
1006863-69-9

tiagabine hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In di-isopropyl ether; ethyl acetate; acetonitrile at 20℃; Product distribution / selectivity;94%
tartaric acid
87-69-4

tartaric acid

tiagabine
115103-54-3

tiagabine

tiagabine tartrate

tiagabine tartrate

Conditions
ConditionsYield
In methanol; acetonitrile Product distribution / selectivity;91%
In tetrahydrofuran; dichloromethane; isopropyl alcohol at 20℃; for 48h; Product distribution / selectivity;
tiagabine
115103-54-3

tiagabine

tiagabine hydrochloride

tiagabine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 20℃; for 1h;90%
With hydrogenchloride In methanol; dichloromethane; chloroform at 3℃; for 24h;
malic acid
617-48-1

malic acid

tiagabine
115103-54-3

tiagabine

tiagabine dl-malate

tiagabine dl-malate

Conditions
ConditionsYield
In methanol; ethyl acetate; acetonitrile at 20℃; for 1h; Product distribution / selectivity;77%
In tetrahydrofuran; dichloromethane; isopropyl alcohol at 20℃; for 48h; Product distribution / selectivity;
D-(+)-camphoric acid
124-83-4

D-(+)-camphoric acid

tiagabine
115103-54-3

tiagabine

tiagabine camphorate

tiagabine camphorate

Conditions
ConditionsYield
In methanol; acetonitrile Product distribution / selectivity;68%
In methanol; dichloromethane at 20℃; for 48h; Product distribution / selectivity;
D-Malic acid
636-61-3

D-Malic acid

tiagabine
115103-54-3

tiagabine

tiagabine d-malate

tiagabine d-malate

Conditions
ConditionsYield
In methanol; ethyl acetate; acetonitrile at 20℃; for 1h;32%
D-tartaric acid
147-71-7

D-tartaric acid

tiagabine
115103-54-3

tiagabine

tiagabine tartrate

tiagabine tartrate

Conditions
ConditionsYield
In methanol; acetonitrile at 20℃; Product distribution / selectivity;
In dichloromethane; ethyl acetate; acetone at 20℃; for 48h; Product distribution / selectivity;

Tiagabine Chemical Properties

Molecule structure of 3-Piperidinecarboxylic acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-, (R)- (CAS NO.115103-54-3):

IUPAC Name: (3R)-1-[4,4-Bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid 
Molecular Weight: 375.548 g/mol
Molecular Formula: C20H25NO2S2 
Density: 1.208 g/cm3 
Melting Point: 192 °C
Boiling Point: 568 °C at 760 mmHg 
Flash Point: 297.3 °C
Index of Refraction: 1.604
Molar Refractivity: 106.97 cm3
Molar Volume: 310.6 cm3
Polarizability: 42.4×10-24 cm3
Surface Tension: 49.8 dyne/cm 
Enthalpy of Vaporization: 89.69 kJ/mol
Vapour Pressure: 9.71E-14 mmHg at 25 °C
XLogP3-AA: 2.7
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 6
Exact Mass: 375.13267
MonoIsotopic Mass: 375.13267
Topological Polar Surface Area: 40.5
Heavy Atom Count: 25
Complexity: 474
Defined Atom StereoCenter Count: 1
Canonical SMILES: CC1=C(SC=C1)C(=CCCN2CCCC(C2)C(=O)O)C3=C(C=CS3)C
Isomeric SMILES: CC1=C(SC=C1)C(=CCCN2CCC[C@H](C2)C(=O)O)C3=C(C=CS3)C
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
InChIKey: PBJUNZJWGZTSKL-MRXNPFEDSA-N
Product Categories: Intermediates & Fine Chemicals; Neurochemicals; Pharmaceuticals

Tiagabine Uses

 3-Piperidinecarboxylic acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-, (R)- (CAS NO.115103-54-3) is used as a GABA uptake inhibitor.

Tiagabine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
Hazardous Substances Data: 115103-54-3(Hazardous Substances Data)

Tiagabine Specification

 3-Piperidinecarboxylic acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-, (R)- (CAS NO.115103-54-3) is also named as HSDB 7527 ; Tiagabina ; Tiagabina [INN-Spanish] ; Tiagabine ; Tiagabinum ; Tiagabinum [INN-Latin] ; UNII-Z80I64HMNP ; (-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acid . 3-Piperidinecarboxylic acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-, (R)- (CAS NO.115103-54-3) is white to off-white crystalline solid.

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