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V113

Sigma-Aldrich

S(+)-γ-Vigabatrin

solid

Synonym(s):

S(+)-γ-Vinyl GABA, S(+)-4-Aminohexenoic acid

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
74046-07-4
Molecular Weight:
129.16
MDL number:
MFCD00274076
UNSPSC Code:
12352200
PubChem Substance ID:
24900710
NACRES:
NA.77

form

solid

optical activity

[α]/D +11.8°, c = 2.5 in H2O(lit.)

color

off-white

solubility

H2O: >20 mg/mL
ethanol: soluble

storage temp.

2-8°C

SMILES string

N[C@@H](CCC(O)=O)C=C

InChI

1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m1/s1

InChI key

PJDFLNIOAUIZSL-RXMQYKEDSA-N

Application

S(+)-γ-Vigabatrin has been used as a standard in ultra-high-performance-liquid-chromatography (UHPLC).

Biochem/physiol Actions

γ-Vigabatrin has the potential to treat infantile spasms and seizures. It exhibits therapeutic effects against cocaine and other addictions.
GABA transaminase inhibitor; anti-convulsant.

Caution

Hygroscopic

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H372

Precautionary Statements

P260 - P264 - P270 - P314 - P501

Hazard Classifications

STOT RE 1

Target Organs

Eyes,Central nervous system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Determination of enantiomeric vigabatrin by derivatization with diacetyl-l-tartaric anhydride followed by ultra-high performance liquid chromatography-quadrupole-time-of-flight mass spectrometry
Zhao J, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1040(5), 199-207 (2017)
Evaluating risks for vigabatrin treatment
Krauss, Gregory L
Epilepsy currents, 9(5), 125-129 (2009)
O M Larsson et al.
Neuropharmacology, 25(6), 617-625 (1986-06-01)
A preferential effect of valproate on gamma-aminobutyric acid (GABA) in the nerve terminal compartment has been proposed. Gamma-vinyl GABA, an irreversible inhibitor of GABA-transaminase (GABA-T) causes a preferential increase in the GABA compartment of the non-nerve terminal. The aim of
M M Robin et al.
European journal of pharmacology, 62(4), 319-327 (1980-04-04)
Unilateral intrastriatal injection of various substances induces a characteristic dyskinetic syndrome in rats. These substances include picrotoxin as well as a series of irreversible GABA-transaminase inhibitors. Using the degree of enzyme inhibition in various brain areas as a measure of

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