gamma-Amino-beta-hydroxybutyric acid

gamma-Amino-beta-hydroxybutyric acid

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
Molar 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

1. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 44–. ISBN 978-3-88763-075-1.
2. Michael Bryant Smith (23 October 2013). Methods of Non-α-Amino Acid Synthesis, Second Edition. CRC Press. pp. 146–. ISBN 978-1-4665-7789-3.
3. Jack R. Cooper; Floyd E. Bloom; Robert H. Roth (2003). The Biochemical Basis of Neuropharmacology. Oxford University Press. pp. 112–. ISBN 978-0-19-514007-1.
4. Melis, Gian B.; Paoletti, A. M.; Mais, V.; Mastrapasqua, N. M.; Strigini, F.; Fruzzetti, F.; Guarnieri, G.; Gambacciani, M.; Fioretti, P. (2014). "Dose-related effects of γ-amino β-hydroxy butyric acid (GABOB) infusion on growth hormone secretion in normal women". Journal of Endocrinological Investigation 5 (2): 101–106. doi:10.1007/BF03350499. ISSN 0391-4097.
5. Hayashi, Takashi (1959). "The inhibitory action of β-hydroxy-γ-aminobutyric acid upon the seizure following stimulation of the motor cortex of the dog". The Journal of Physiology 145 (3): 570–578. doi:10.1113/jphysiol.1959.sp006163. ISSN 0022-3751.
6. De Maio, D.; Pasquariello, G. (1963). "Gamma-amino-beta-hydroxybutyric acid (GABOB) and brain serotonin". Psychopharmacologia 5 (1): 84–86. doi:10.1007/BF00405577. ISSN 0033-3158.
7. Chemello R, Giaretta D, Pellegrini A, Testa G (1980). "[Effect of gamma-amino-beta-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity]" [Effect of γ-amino-β-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity]. Rivista di Neurologia (in Italian) 50 (4): 253–268. PMID 7466221.
8. García-Flores E, Farías R (1997). "γ-Amino-β-hydroxybutyric acid as add-on therapy in adult patients with severe focal epilepsy". Stereotactic and Functional Neurosurgery 69 (1–4 Pt 2): 243–236. doi:10.1159/000099882. PMID 9711762.
9. Roberts E, Krause DN, Wong E, Mori A (1981). "Different Efficacies of d- and l-γ-Amino-β-Hydroxybutyric Acids in GABA Receptor and Transport Test Systems" (pdf). Journal of Neuroscience 1 (2): 132–140. PMID 6267220.
10. Lapin I (2001). "Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug". CNS Drug Rev 7 (4): 471–81. doi:10.1111/j.1527-3458.2001.tb00211.x. PMID 11830761.