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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
Pricing and availability is not currently available.

form

solid

Quality Level

100

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).[1]

Biochem/physiol Actions

γ-Vigabatrin has the potential to treat infantile spasms and seizures. It exhibits therapeutic effects against cocaine and other addictions.[2]
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

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Certificates of Analysis (COA)

Lot/Batch Number
118H4677V

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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)
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
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

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