An irreversible inhibitor of GABA-T
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Gabaculine (hydrochloride)

Item No. 24209

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-amino-1,3-cyclohexadiene-1-carboxylic acid, monohydrochloride
CAS Number
59556-17-1
Molecular Formula
C7H9NO2 • HCl
Formula Weight
175.6
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 0.2 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
276 nm
SMILES
NC1C=CC=C(C(O)=O)C1.Cl
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
InChi Key
OBZFLUDUSNCZKL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

    $213

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    10 mg

    $376

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    Product Description

    Gabaculine is a naturally occurring, conformationally constrained analog of GABA and an irreversible inhibitor of GABA transaminase (GABA-T; Ki = 2.9 μM).1 It irreversibly inhibits D-amino acid transaminase, L-alanine transaminase, and L-aspartate transaminase with Ki values of 0.1, 1, and 55 mM, respectively.2 Gabaculine also irreversibly inhibits ornithine aminotransferase in vitro and in mouse brain and liver homogenates, where ornithine aminotransferase activity is suppressed for over 24 hours when administered at a dose of 50 mg/kg.3 Gabaculine increases latency to convulsion in the 3-mercaptopropionic acid-induced and minimal electroshock-induced seizure models (ED50s = 135 and 200 mg/kg, respectively) and inhibits 3-mercaptopropionic acid-induced increases in glutamic acid decarboxylase (GAD) activity and GABA-T activity in mice (ED50s =135 mg/kg), however, the doses fall above the LD50 value of 62 mg/kg.4 Gabaculine (135 mg/kg, i.p.) elevates concentrations of GABA in mouse brain by over 500% and knocks out GABA-T activity to below detection limits.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rando, R.R. Mechanism of the irreversible inhibition of γ-aminobutyric acid--ketoglutaric acid transaminase by the neurotoxin gabaculine. Biochem J. 16(21), 4604-4610 (1977).

    2. Soper, T.S., and Manning, J.M. Inactivation of pyridoxal phosphate enzymes by gabaculine. Correlation with enzymic exchange of β-protons. The Journal of Biological Chemisty 257(23), 13930-13936 (1982).

    3. Jung, M.J., and Seiler, N. Enzyme-activated irreversible inhibitors of L-ornithine:2-oxoacid aminotransferase. Demonstration of mechanistic features of the inhibition of ornithine aminotransferase by 4-aminohex-5-ynoic acid and gabaculine and correlation with in vivo activity. The Journal of Biological Chemisty 253(20), 7431-7439 (1978).

    4. Löscher, W. 3-Mercaptopropionic acid: convulsant properties, effects on enzymes of the γ-aminobutyrate system in mouse brain and antagonism by certain anticonvulsant drugs, aminooxyacetic acid and gabaculine. Biochem. Pharmacol. 28(8), 1397-1407 (1979).