WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 319920
Description: GABOB, also known as γ-Amino-β-hydroxybutyric acid, β-hydroxy-γ-aminobutyric acid, β-hydroxy-GABA, is an anticonvulsant which is used for the treatment of epilepsy in Europe, Japan, and Mexico. 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.
MedKoo Cat#: 319920
Name: GABOB (beta-hydroxy-GABA)
Chemical Formula: C4H9NO3
Exact Mass: 119.0582
Molecular Weight: 119.12
Elemental Analysis: C, 40.33; H, 7.62; N, 11.76; O, 40.29
Synonym: GABOB; β-hydroxy-GABA; beta-hydroxy-GABA; γ-Amino-β-hydroxybutyric acid; brand names Gamibetal, Gabomade, Aminoxan, Bogil, Diastal, Gabimex, Gaboril, Kolpo.
IUPAC/Chemical Name: (3S)-4-amino-3-hydroxybutanoic acid
InChi Key: YQGDEPYYFWUPGO-VKHMYHEASA-N
InChi Code: InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1
SMILES Code: O=C(O)C[C@H](O)CN
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. GABOB has two stereoisomers, with the (3S) isomer d-GABOB being around twice as potent an anticonvulsant as the (3R) isomer l-GABOB. 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), and pregabalin (β-isobutyl-GABA).
1: Yamamoto I, Absalom N, Carland JE, Doddareddy MR, Gavande N, Johnston GA, Hanrahan JR, Chebib M. Differentiating enantioselective actions of GABOB: a possible role for threonine 244 in the binding site of GABA(C) ρ(1) receptors. ACS Chem Neurosci. 2012 Sep 19;3(9):665-73. Epub 2012 Apr 26. PubMed PMID: 23019493; PubMed Central PMCID: PMC3447397.
2: Du Z, Chen Z, Chen Z, Yu X, Hu W. Dirhodium-catalyzed enantioselective C-H insertion of N-(2-benzyloxyethyl)-N-(tert-butyl)diazoacetamide and its application for the synthesis of chiral GABOB. Chirality. 2004 Oct;16(8):516-9. PubMed PMID: 15290686.
3: Nakao J, Hasegawa T, Hashimoto H, Noto T, Nakajima T. Formation of GABOB from 2-hydroxyputrescine and its anticonvulsant effect. Pharmacol Biochem Behav. 1991 Oct;40(2):359-66. PubMed PMID: 1805240.
4: Banfi S, Fonio W, Allievi E, Pinza M, Dorigotti L. Cyclic GABA-GABOB analogues. IV. Activity on learning and memory. Farmaco Sci. 1984 Jan;39(1):16-22. PubMed PMID: 6538512.
5: Melis GB, Paoletti AM, Mais V, Mastrapasqua NM, Strigini F, Fruzzetti F, Guarnieri G, Gambacciani M, Fioretti P. Dose-related effects of gamma-amino beta-hydroxy butyric acid (GABOB) infusion on growth hormone secretion in normal women. J Endocrinol Invest. 1982 Mar-Apr;5(2):101-6. PubMed PMID: 7096918.
6: Pellegata R, Pinza M, Pifferi G, Gaiti A, Mozzi R, Tirillini B, Porcellati G. Cyclic GABA-GABOB analogues. III - Synthesis and biochemical activity of new alkyl and acyl derivatives of 4-hydroxy-2-pyrrolidinone. Farmaco Sci. 1981 Oct;36(10):845-55. PubMed PMID: 7308456.
7: Bonardi G, Mondino A, Silvestri S, Zanolo G. Absorption, distribution and excretion of DL-gamma-amino-beta-hydroxybutyric acid-1-14C (GABOB-1-14C) in the rat. Arzneimittelforschung. 1981;31(11):1910-3. PubMed PMID: 7198473.
8: Takahara J, Yunoki S, Yakushiji W, Yamauchi J, Hosogi H, Ofuji T. Stimulatory effects of gamma-aminohydroxybutyric acid (GABOB) on growth hormone, prolactin and cortisol release in man. Horm Metab Res. 1980 Jan;12(1):31-4. PubMed PMID: 6244218.
9: Matsushita K, Gjessing LR. Analysis of gamma-amino-beta-hydroxy butyric acid (GABOB) by chromatography and electrophoresis. J Chromatogr. 1979 Mar 1;162(3):427-32. PubMed PMID: 528609.
10: Pinza M, Pifferi G. Cyclic GABA-GABOB analogues. II - Synthesis of new 2-oxo and 2,5-dioxo-delta3-pyrroline derivatives. Farmaco Sci. 1978 Feb;33(2):130-41. PubMed PMID: 631318.
11: Pifferi G, Pinza M. Cyclic Gaba-Gabob analogues I - Synthesis of new 4-hydroxy-2-pyrrolidinone derivatives. Farmaco Sci. 1977 Aug;32(8):602-13. PubMed PMID: 891913.
12: Abe H, Kato Y, Chihara K, Ohgo S, Iwasaki Y. Growth hormone release by gamma-aminobutyric acid (GABA) and gamma-amino-beta-hydroxybutyric acid (GABOB) in the rat. Endocrinol Jpn. 1977 Apr;24(2):229-31. PubMed PMID: 872825.
13: Nistico G. Effects of gaba, gabob and some anticonvulsant drugs on dibutyryl cyclic AMP evoked seizures. Int J Clin Pharmacol Biopharm. 1977 Jan;15(1):19-22. PubMed PMID: 190179.
14: Tartara A, Arrigo A, Scamoni C, Presazzi A. [Clinico-experimental studies in the treatment of epilepsy with GABOB-diazepam]. Minerva Med. 1973 May 23;64(36):1943-8. Italian. PubMed PMID: 4578343.
15: Mille T, Scamoni C, Presazzi A. [Clinical and electroencephalographic studies of Gabob-Diazepam effects on young children with behavior disorders]. Minerva Pediatr. 1973 Apr 14;25(13):593-603. Italian. PubMed PMID: 4708945.
16: Di Marco A. [Effect of a combination of GABOB and plant extracts on the behavior of hospitalized children]. Minerva Pediatr. 1972 Dec 15;24(43):2150-61. Italian. PubMed PMID: 4652220.
17: Amore F, Cavazzuti GB. [Clinical and statistical evaluation of GABOB in behavior disorders in young children]. Minerva Med. 1971 Apr 11;62(29):1503-13. Italian. PubMed PMID: 4936825.
18: Matsumoto K, Omoto T, Nanba S, Miyamoto T. [Influence of GABOB and GABA solutions on the cortical evoked potentials]. No To Shinkei. 1971 Apr;23(4):357-63. Japanese. PubMed PMID: 5108042.
19: Nagai K, Sano A, Yamaguchi K, Kodaira Y. Studies on the synergistic action and anti-ulcerous activity of cortisone-GABOB. Arzneimittelforschung. 1971 Jan;21(1):96-7. PubMed PMID: 5108207.
20: Colucci D'Amato F. [Chemico-clinical evaluation of Gabob in schizophrenic patients]. Osp Psichiatr. 1970 Jul-Sep;38(3):377-81. Italian. PubMed PMID: 5514594.