gamma-Amino-beta-hydroxybutyric acid

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gamma-Amino-beta-hydroxybutyric acid
GABOB.png
GABOB3d.png
Systematic (IUPAC) name
4-amino-3-hydroxybutanoic acid
Identifiers
CAS Number 352-21-6
PubChem CID: 2149
ChemSpider 2064
ChEMBL CHEMBL93515
Chemical data
Formula C4H9NO3
Molecular mass 119.12 g/mol

γ-Amino-β-hydroxybutyric acid (GABOB) (brand names Gamibetal, Gabomade, Aminoxan, Bogil, Diastal, Gabimex, Gaboril, Kolpo), or β-hydroxy-γ-aminobutyric acid (β-hydroxy-GABA), is an anticonvulsant which is used for the treatment of epilepsy in Europe, Japan, and Mexico.[1][2] It is also an endogenous active metabolite and analogue of the neurotransmitter γ-aminobutyric acid (GABA), and for this reason, may function as a neurotransmitter itself.[2][3][4][5] Relative to GABA, GABOB has more potent inhibitory effects on the central nervous system, perhaps due to its greater capacity to cross the blood-brain-barrier.[5][6] However, GABOB is of relatively low potency as an anticonvulsant when used by itself, and is more useful as an adjuvant treatment used alongside another anticonvulsant.[7][8] GABOB has two stereoisomers, with the (3S) isomer d-GABOB being around twice as potent an anticonvulsant as the (3R) isomer l-GABOB.[9]

GABOB (β-hydroxy-GABA) is a close structural analogue of GABA (see GABA analogue), as well as of γ-hydroxybutyric acid (GHB), phenibut (β-phenyl-GABA), baclofen (β-(4-chlorophenyl)-GABA),[10] and pregabalin (β-isobutyl-GABA).

References

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