Tiagabine

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Names

[ Name ]:
Tiagabine

[Synonym ]:
(-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochloride
(R)-(-)-N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipecotic acid
acide (3R)-1-[4,4-bis(3-méthylthiophén-2-yl)but-3-én-1-yl]pipéridine-3-carboxylique chlorhydrate
NO-05-0328
Gabitril / NNC 05-328
Abbott-70569.1
(R)-N-[4,4-di-(3-methylthien-2-yl)but-3-enyl] nipecotic acid hydrochloride
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride (1:1)
(3R)-1-[4,4-Bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidin-3-carbonsäurehydrochlorid
TIGABINE
3-Piperidinecarboxylic acid, 1-[4,4-bis(3-methyl-2-thienyl)-3-buten-1-yl]-, (3R)-, hydrochloride (1:1)
(R)-1-[4,4-bis(3-methyl-thien-2-yl)-3-butenyl]-3-piperidinecarboxylic acid
(3R)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid hydrochloride
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride
TGB
Tiagabine
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride (1:1)
no328
4-bis(3-methyl-2-thienyl)-3-butenyl)-1-((r)-3-piperidinecarboxylicaci
(R)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidinecarboxylic acid hydrochloride (1:1)
Abbott-70569.HCl
MFCD00865317
3-piperidinecarboxylic acid, 1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-, (3R)-, hydrochloride

Chemical & Physical Properties

[ Density]:
1.208 g/cm3

[ Boiling Point ]:
568ºC at 760 mmHg

[ Melting Point ]:
192oC dec.

[ Molecular Formula ]:
C₂₀H₂₅NO₂S₂

[ Molecular Weight ]:
375.55

[ Flash Point ]:
297.3ºC

[ PSA ]:
97.02000

[ LogP ]:
5.78470

[ Vapour Pressure ]:
9.71E-14mmHg at 25°C

[ Index of Refraction ]:
1.604

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TM6128245

CHEMICAL NAME :: 3-Piperidinecarboxylic acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-, (R)-

CAS REGISTRY NUMBER :: 115103-54-3

LAST UPDATED :: 199801

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C20-H25-N-O2-S2.Cl-H

MOLECULAR WEIGHT :: 412.04

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 630 mg/kg/21D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: EPIRE8 Epilepsy Research. (Elsevier Science Publishers B.V., POB 1527, 1000 BM, Amsterdam, Netherlands) V.1- 1987- Volume(issue)/page/year: 19,205,1994

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36/37-S22

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

ethyl (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylate
2-Bromo-3-methylthiophene
3-Methylthiophene-2-aldehyde
bis(3-methylthiophen-2-yl)methanone
4-BROMO-1,1-BIS(3-METHYL-2-THIENYL)-1-BUTENE
4-Bromo-1,1-bis(3-methyl-2-thienyl)-1-butanol
4,4-bis(3-methyl-2-thienyl)-3-buten-1-ol
Arecoline hydrobromide