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Gabaculine information


Gabaculine
Names
IUPAC name
5-Aminocyclohexa-1,3-diene-1-carboxylic acid
Identifiers
CAS Number
  • 59556-29-5 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 3327 ☒N
PubChem CID
  • 3445
UNII
  • 3F3ENU341O checkY
CompTox Dashboard (EPA)
  • DTXSID50868990 DTXSID90274399, DTXSID50868990 Edit this at Wikidata
InChI
  • InChI=1S/C7H9NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-3,6H,4,8H2,(H,9,10) ☒N
    Key: KFNRJXCQEJIBER-UHFFFAOYSA-N ☒N
  • InChI=1/C7H9NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-3,6H,4,8H2,(H,9,10)
    Key: KFNRJXCQEJIBER-UHFFFAOYAL
SMILES
  • O=C(O)\C1=C\C=C/C(N)C1
Properties
Chemical formula
C7H9NO2
Molar mass 139.154 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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]

  1. ^ Kobayashi K, Miyazawa S, Endo A (April 1977). "Isolation and inhibitory activity of gabaculine, a new potent inhibitor of gamma-aminobutyrate aminotransferase produced by a Streptomyces". FEBS Letters. 76 (2): 207–10. doi:10.1016/0014-5793(77)80153-1. PMID 862902.
  2. ^ Rando RR (October 1977). "Mechanism of the irreversible inhibition of gamma-aminobutyric acid-alpha-ketoglutaric acid transaminase by the neurotoxin gabaculine". Biochemistry. 16 (21): 4604–10. doi:10.1021/bi00640a012. PMID 410442.
  3. ^ Irifune M, Katayama S, Takarada T, et al. (December 2007). "MK-801 enhances gabaculine-induced loss of the righting reflex in mice, but not immobility". Can J Anaesth. 54 (12): 998–1005. doi:10.1007/BF03016634. PMID 18056209.
  4. ^ Allan RD, Johnston GAR, Twitchin B. Effects of Gabaculine on uptake, binding and metabolism of GABA. Neuroscience Letters. 1977;4:51-54.
  5. ^ Høg S, Greenwood JR, Madsen KB, Larsson OM, Frølund B, Schousboe A, Krogsgaard-Larsen P, Clausen RP (2006). "Structure-activity relationships of selective GABA uptake inhibitors". Current Topics in Medicinal Chemistry. 6 (17): 1861–82. doi:10.2174/156802606778249801. PMID 17017962. Archived from the original on 2013-04-14.
  6. ^ Santa Cruz Biotechnology, Inc. "Gabaculine Material Safety Data Sheet". Retrieved 5 December 2014.
  7. ^ a b Mutsui, Yoshiki; Deguchi, Takehiko (1977). "Effects of gabaculine, a new potent inhibitor of gamma-aminobutyrate transaminase, on brain gamma-aminobutyrate content and convulsions in mice". Life Sciences. 20 (7): 1291–1296. doi:10.1016/0024-3205(77)90505-7. PMID 850479.

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Gabaculine

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Arecaidine

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GABA reuptake inhibitor

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GABA

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hyperforin, tiagabine.[citation needed] GABA transaminase inhibitors: gabaculine, phenelzine, valproate, vigabatrin, lemon balm (Melissa officinalis)....

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Glutamate decarboxylase

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Vigabatrin

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GABA analogue

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antagonist Arecaidine – constituent of areca nuts; GABA reuptake inhibitor Gabaculine – neurotoxin; GABA-T inhibitor and GABA reuptake inhibitor Gabapentin...

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Valproate

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Pyridoxal phosphate

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its lack of specificity has prompted further designs of ALR inhibitors. Gabaculine and Vigabatrin inhibit GABA aminotransferase Canaline and 5-fluoromethylornithine...

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Isoniazid

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β-Alanine Arecaidine CI-966 DABA Deramciclane (EGIS-3886, EGYT-3886) EF-1502 Gabaculine Guvacine Ibotenic acid Muscimol Nipecotic acid NNC 05-2090 NO-711 Riluzole...

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Phenelzine

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C7H9NO2

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mass: 139.0633 u) may refer to: Ammonium benzoate Deferiprone (Ferriprox) Gabaculine This set index page lists chemical structure articles associated with...

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Muscimol

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β-Alanine Arecaidine CI-966 DABA Deramciclane (EGIS-3886, EGYT-3886) EF-1502 Gabaculine Guvacine Ibotenic acid Muscimol Nipecotic acid NNC 05-2090 NO-711 Riluzole...

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Ibotenic acid

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Riluzole

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β-Alanine Arecaidine CI-966 DABA Deramciclane (EGIS-3886, EGYT-3886) EF-1502 Gabaculine Guvacine Ibotenic acid Muscimol Nipecotic acid NNC 05-2090 NO-711 Riluzole...

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Cycloserine

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Betaine transporter

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GABA transporter

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Valpromide

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Tiagabine

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