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Merck

V8261

(±)-Vigabatrin

Synonym(s):

(R,S)-4-Amino-5-hexenoic acid, (±)-γ-Vinyl-GABA, (±)-4-Aminohexenoic acid

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
68506-86-5
Molecular Weight:
129.16
NACRES:
NA.77
PubChem Substance ID:
24278202
UNSPSC Code:
12352200
EC Number:
270-929-6
MDL number:
MFCD00274577

InChI key

PJDFLNIOAUIZSL-UHFFFAOYSA-N

InChI

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

SMILES string

NC(CCC(O)=O)C=C

originator

Lundbeck

Quality Level

200

Gene Information

human ... ABAT(18), GABBR1(2550), GABBR2(9568), GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)

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Biochem/physiol Actions

Irreversible GABA transaminase inhibitor. Increases intracellular concentration of GABA in nerve endings; possesses antiepileptic activity.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABA Transporters, GABAA Receptors and Glutamate/GABA Synthesis and Metabolism pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Lundbeck. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H372

Hazard Classifications

STOT RE 1

target_organs

Eyes,Central nervous system

Storage Class

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000477776
0000477777
0000477777
0000477776
0000078003

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Olga Doszyn et al.
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Mechanistic target of rapamycin complex 1 (mTORC1) is an integration hub for extracellular and intracellular signals necessary for brain development. Hyperactive mTORC1 is found in autism spectrum disorder (ASD) characterized by atypical reactivity to sensory stimuli, among other symptoms. In
The potential value of a negative finding: an illustrative example.
Kenneth Silverman et al.
JAMA psychiatry, 70(6), 571-572 (2013-04-12)
R S Fisher
Brain research. Brain research reviews, 14(3), 245-278 (1989-07-01)
The study of mechanisms of the epilepsies requires employment of animal models. Choice of a model system depends upon several factors, including the question to be studied, the type of epilepsy to be modelled, familiarity and convenience. Over 50 models
Nicolas Froger et al.
Advances in experimental medicine and biology, 775, 69-83 (2013-02-09)
Retinal ganglion cells (RGCs) are spiking neurons, which send visual information to the brain, through the optic nerve. RGC degeneration occurs in retinal diseases, either as a primary process or secondary to photoreceptor loss. Mechanisms involved in this neuronal degeneration
Jose I Juncosa et al.
Bioorganic & medicinal chemistry, 21(4), 903-911 (2013-01-12)
We have synthesized three analogues of 4-amino-5-fluorohexanoic acids as potential inactivators of γ-aminobutyric acid aminotransferase (GABA-AT), which were designed to combine the potency of their shorter chain analogue, 4-amino-5-fluoropentanoic acid (AFPA), with the greater enzyme selectivity of the antiepileptic vigabatrin
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