Gamma-Amino-beta-hydroxybutyric acid

γ-Amino-β-hydroxybutyric acid

Clinical data
Trade names	Gamibetal, others
Other names	Buxamine; Buxamina; Bussamina; γ-Amino-β-hydroxybutyric acid; GABOB; β-Hydroxy-γ-aminobutyric acid; β-Hydroxy-GABA
Identifiers
IUPAC name (±)-4-amino-3-hydroxybutanoic acid
CAS Number	924-49-2 352-21-6
PubChem CID	2149
ChemSpider	2064
UNII	1ZHM019FLD
KEGG	D00174
ChEBI	CHEBI:16080
ChEMBL	ChEMBL93515
CompTox Dashboard (EPA)	DTXSID1045877
ECHA InfoCard	100.011.916
Chemical and physical data
Formula	C4H9NO3
Molar mass	119.120 g·mol−1
3D model (JSmol)	Interactive image
SMILES C(C(CN)O)C(=O)O
InChI InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8) Key:YQGDEPYYFWUPGO-UHFFFAOYSA-N

γ-Amino-β-hydroxybutyric acid (GABOB), also known as β-hydroxy-γ-aminobutyric acid (β-hydroxy-GABA), and sold under the brand name Gamibetal among others, is an anticonvulsant which is used for the treatment of epilepsy in Europe, Japan, and Mexico. It is a GABA analogue, or an analogue of the neurotransmitter γ-aminobutyric acid (GABA), and has been found to be an endogenous metabolite of GABA.

Medical uses

GABOB is an anticonvulsant and is used in the treatment of epilepsy.

Pharmacology

GABOB is a GABA receptor agonist. It has two stereoisomers, and shows stereoselectivity in its actions. Specifically, (R)-(–)-GABOB is a moderate-potency agonist of the GABA_B receptor, while (S)-(+)-GABOB is a partial agonist of the GABA_B receptor and an agonist of the GABA_A receptor. (S)-(+)-GABOB is around twice as potent an anticonvulsant as (R)-(–)-GABOB. GABOB is used medically as a racemic mixture.

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. 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.

Chemistry

GABOB, or 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), and pregabalin (β-isobutyl-GABA).

Society and culture

Generic name

GABOB has been referred to by the generic name buxamine or buxamina.

Brand names

GABOB is sold primarily under the brand name Gamibetal. It has also been marketed under a variety of other brand names including Aminoxan, Bogil, Diastal, Gabimex, Gabomade, Gaboril, Gamalate, and Kolpo.