Gabaculine
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
5-Aminocyclohexa-1,3-diene-1-carboxylic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H9NO2 | |
| Molar mass | 139.154 g·mol−1 |
| Pharmacology | |
| Drug class | GABA-T inhibitor; GABA reuptake inhibitor; GABA transporter 1 (GAT-1) inhibitor; Anticonvulsant |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gabaculine is a naturally occurring neurotoxin first isolated from the bacteria Streptomyces toyacaensis,[1] which acts as a potent and irreversible GABA transaminase inhibitor,[2][3] and also a GABA reuptake inhibitor.[4][5] Gabaculine is also known as 3-amino-2,3-dihydrobenzoic acid hydrochloride [6] and 5-amino cyclohexa-1,3 dienyl carboxylic acid.[7] Gabaculine increased GABA levels in the brain and had an effect on convulsivity in mice.[7]
Gabaculine includes a comparable structure to GABA and a dihydrobenzene ring. This comparable GABA structure is used in order to be able to take the place of GABA during the first steps of transamination, including transaldimination and 1,3-prototrophic shift to the pyridoxamine imine.[8] Following this, a proton from the dihydrobenzene ring is abstracted by an enzymatic base, thus causing the ring to become aromatic.[8] The aromatic stabilization energy of the aromatic ring is what causes this reaction to be irreversible, thus causing the complex not to react further.[8]