Gabaculine HCl
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MedKoo CAT#: 330119

CAS#: 59556-17-1 (HCl)

Description: Gabaculine is a naturally occurring, conformationally constrained analog of GABA and an irreversible inhibitor of GABA transaminase (GABA-T; Ki = 2.9 μM). Gabaculine alters plastid development and differentially affects abundance of plastid-encoded DPOR and nuclear-encoded GluTR and FLU-like proteins in spruce cotyledons.


Chemical Structure

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Gabaculine HCl
CAS# 59556-17-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 330119
Name: Gabaculine HCl
CAS#: 59556-17-1 (HCl)
Chemical Formula: C7H10ClNO2
Exact Mass: 175.04
Molecular Weight: 175.612
Elemental Analysis: C, 47.88; H, 5.74; Cl, 20.19; N, 7.98; O, 18.22

Price and Availability

Size Price Availability Quantity
5.0mg USD 325.0 2 Weeks
10.0mg USD 550.0 2 Weeks
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Related CAS #: 59556-29-5 (free base)   59556-17-1 (HCl)    

Synonym: Gabaculine HCl; Gabaculine hydrochlorlide; 708-B

IUPAC/Chemical Name: 5-amino-1,3-cyclohexadiene-1-carboxylic acid, monohydrochloride

InChi Key: OBZFLUDUSNCZKL-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H9NO2.ClH/c8-6-3-1-2-5(4-6)7(9)10;/h1-3,6H,4,8H2,(H,9,10);1H

SMILES Code: O=C(C1=CC=CC(N)C1)O.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 175.612 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Bellucci M, De Marchis F, Ferradini N, Pompa A, Veronesi F, Rosellini D. A mutant Synechococcus gene encoding glutamate 1-semialdehyde aminotransferase confers gabaculine resistance when expressed in tobacco plastids. Plant Cell Rep. 2015 Dec;34(12):2127-36. doi: 10.1007/s00299-015-1856-z. Epub 2015 Aug 12. PubMed PMID: 26265112.

2: Demko V, Pavlovic A, Hudák J. Gabaculine alters plastid development and differentially affects abundance of plastid-encoded DPOR and nuclear-encoded GluTR and FLU-like proteins in spruce cotyledons. J Plant Physiol. 2010 Jun 15;167(9):693-700. doi: 10.1016/j.jplph.2009.12.008. Epub 2010 Feb 2. PubMed PMID: 20129699.

3: Orriss GL, Patel TR, Sorensen J, Stetefeld J. Absence of a catalytic water confers resistance to the neurotoxin gabaculine. FASEB J. 2010 Feb;24(2):404-14. doi: 10.1096/fj.09-138297. Epub 2009 Sep 28. PubMed PMID: 19786580.

4: Irifune M, Katayama S, Takarada T, Shimizu Y, Endo C, Takata T, Morita K, Dohi T, Sato T, Kawahara M. MK-801 enhances gabaculine-induced loss of the righting reflex in mice, but not immobility. Can J Anaesth. 2007 Dec;54(12):998-1005. PubMed PMID: 18056209.

5: Drazic G, Bogdanovic M. Gabaculine does not inhibit cytokinin-stimulated biosynthesis of chlorophyll in Pinus nigra seedlings in the dark. Plant Sci. 2000 May 15;154(1):23-29. PubMed PMID: 10725555.

6: Fu M, Silverman RB. Isolation and characterization of the product of inactivation of gamma-aminobutyric acid aminotransferase by gabaculine. Bioorg Med Chem. 1999 Aug;7(8):1581-90. PubMed PMID: 10482450.

7: Shah SA, Shen BW, Brünger AT. Human ornithine aminotransferase complexed with L-canaline and gabaculine: structural basis for substrate recognition. Structure. 1997 Aug 15;5(8):1067-75. PubMed PMID: 9309222.

8: Gilbert SM, Allison GG, Rogers LJ, Smith AJ. Expression of genes involved in phycocyanin biosynthesis following recovery of Synechococcus PCC 6301 from nitrogen starvation, and the effect of gabaculine on cpcBa transcript levels. FEMS Microbiol Lett. 1996 Jun 15;140(1):93-8. PubMed PMID: 8666206.

9: Howe G, Mets L, Merchant S. Biosynthesis of cytochrome f in Chlamydomonas reinhardtii: analysis of the pathway in gabaculine-treated cells and in the heme attachment mutant B6. Mol Gen Genet. 1995 Jan 20;246(2):156-65. PubMed PMID: 7862086.

10: Behar KL, Boehm D. Measurement of GABA following GABA-transaminase inhibition by gabaculine: a 1H and 31P NMR spectroscopic study of rat brain in vivo. Magn Reson Med. 1994 Jun;31(6):660-7. PubMed PMID: 7914662.

11: Chappell DL, Rogers LJ, Smith AJ. Synechococcus PCC6301 mutants possessing resistance to the tetrapyrrole biosynthesis inhibitor gabaculine. Biochem Soc Trans. 1992 Aug;20(3):285S. PubMed PMID: 1426569.

12: Smith MA, Grimm B. Gabaculine resistance of Synechococcus glutamate 1-semialdehyde aminotransferase. Biochemistry. 1992 Apr 28;31(16):4122-7. PubMed PMID: 1567858.

13: Grimm B, Smith AJ, Kannangara CG, Smith M. Gabaculine-resistant glutamate 1-semialdehyde aminotransferase of Synechococcus. Deletion of a tripeptide close to the NH2 terminus and internal amino acid substitution. J Biol Chem. 1991 Jul 5;266(19):12495-501. PubMed PMID: 1905724.

14: Asakura T, Sakurai T, Hayashi T, Matsuda M. Effect of gabaculine on metabolism and release of gamma-aminobutyric acid (GABA) formed from 4-aminobutyraldehyde in synaptosomes. Biochem Pharmacol. 1991 Jul 5;42(2):447-50. PubMed PMID: 1677570.

15: Cubells JF, Ndubuka C, Makman MH. 2-amino-4-phosphonobutyric acid exerts a light-dependent effect on post-gabaculine levels of retinal gamma-aminobutyric acid (GABA): evidence that ON synaptic pathways regulate retinal GABAergic transmission. J Neurochem. 1991 Jul;57(1):46-52. PubMed PMID: 1646863.

16: Anderson CM, Gray JC. Effect of Gabaculine on the Synthesis of Heme and Cytochrome f in Etiolated Wheat Seedlings. Plant Physiol. 1991 Jun;96(2):584-7. PubMed PMID: 16668225; PubMed Central PMCID: PMC1080810.

17: Kaneko M, Fujimoto S, Kikugawa M, Tamaki N. Irreversible inhibition of D-3-aminoisobutyrate-pyruvate aminotransferase by gabaculine. FEBS Lett. 1990 Dec 10;276(1-2):115-8. PubMed PMID: 2125004.

18: Hinko CN, Rozanov C. The role of bicuculline, aminooxyacetic acid and gabaculine in the modulation of ethanol-induced motor impairment. Eur J Pharmacol. 1990 Jul 3;182(2):261-71. PubMed PMID: 2397743.

19: Asakura T, Matsuda M. Effect of gabaculine on metabolism and release of gamma-aminobutyric acid in synaptosomes. Neurochem Res. 1990 Mar;15(3):295-300. PubMed PMID: 1973270.

20: Steulet AF, Hauser K, Martin P, Leonhardt T, Bandelier V, Gunst F, Bernasconi R. Reversal by apomorphine of the gabaculine-induced GABA accumulation in mouse cortex. Eur J Pharmacol. 1989 Dec 19;174(2-3):161-70. PubMed PMID: 2630298.