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Gabaculine

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Gabaculine
Names
IUPAC name (RS)-5-amino-1-cyclohexa-1,3-dienecarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • C1C(C=CC=C1C(=O)O)N
Properties
Chemical formula C7H9NO2
Molar mass 139.15186
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Gabaculine is a naturally occurring neurotoxin first isolated from the bacteria Streptomyces toyacaensis, which acts as a potent and irreversible GABA transaminase inhibitor, and also a GABA reuptake inhibitor.

References

  1. Kobayashi K, Miyazawa S, Endo A (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. Rando RR (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. {{cite journal}}: Unknown parameter |month= ignored (help)
  3. Irifune M, Katayama S, Takarada T; et al. (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. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
GABA receptor modulators
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAATooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators


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