γ-Acetylenic GABA[ 1]
Names
IUPAC name
4-Aminohex-5-ynoic acid
Other names
Γ-Acetylenic-GABA 4-Amino-5-hexynoic acid
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.165.059
EC Number
UNII
InChI=1S/C6H9NO2/c1-2-5(7)3-4-6(8)9/h1,5H,3-4,7H2,(H,8,9)
Key: BJNIHWSOVCDBHS-UHFFFAOYSA-N
Properties
C 6 H 9 N O 2
Molar mass
127.143 g·mol−1
Hazards
GHS labelling :[ 2]
Warning
H315 , H319 , H335
P261 , P264 , P264+P265 , P271 , P280 , P302+P352 , P304+P340 , P305+P351+P338 , P319 , P321 , P332+P317 , P337+P317 , P362+P364 , P403+P233 , P405 , P501
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
γ-Acetylenic GABA , also known as 4-aminohex-5-ynoic acid is a potent and irreversible inhibitor of GABA-T .[ 3]
Mechanism of action
Like other GABA-T inhibitors , γ-acetylenic GABA causes GABA levels in the brain to be elevated. This is due to 4-aminobutyrate transaminase being the enzyme that converts γ-aminobutyric acid to L -glutamate . Inhibiting the enzyme stops this conversion from happening.
Potential uses
Anti convulsant
Continuous administration of γ-acetylenic GABA on rats during four days was able to reduce or completely stop seizures that were induced by amygdala overstimulation.[ 4]
Treatment of tardive dyskinesia
A study has showed that γ-acetylenic GABA could reduce tardive dyskinesia symptoms. This result mostly happened in subjects receiving higher doses.[ 5]
References
^ https://pubchem.ncbi.nlm.nih.gov/compound/4-Aminohex-5-ynoic-acid
^ "4-Aminohex-5-ynoic acid" . pubchem.ncbi.nlm.nih.gov .
^ Tell, Guy; Böhlen, Peter; Schechter, Paul J.; Koch-Weser, Jan; Agid, Yves; Bonnet, A. M.; Coquillat, Gilles; Chazot, Guy; Fischer, Catherine (February 1981). "Treatment of Huntington disease with γ ‐acetylenic GABA, an irreversible inhibitor of GABA‐ transaminase: Increased CSF GABA and homocarnosine without clinical amelioration" . Neurology . 31 (2): 207. doi :10.1212/WNL.31.2.207 . ISSN 0028-3878 .
^ Myslobodsky, M. S.; Valenstein, E. S. (April 1980). "Amygdaloid kindling and the GABA system" . Epilepsia . 21 (2): 163–175. doi :10.1111/j.1528-1157.1980.tb04058.x . hdl :2027.42/66112 . ISSN 0013-9580 . PMID 7358042 .
^ Casey, Daniel E.; Gerlach, Jes; Magelund, Gerhard; Christensen, Torben Rosted (1980-12-01). "γ-Acetylenic GABA in Tardive Dyskinesia" . Archives of General Psychiatry . 37 (12): 1376–1379. doi :10.1001/archpsyc.1980.01780250062007 . ISSN 0003-990X .
Transporter
GAT Tooltip GABA transporter VIAAT Tooltip Vesicular inhibitory amino acid transporter
Enzyme
GAD Tooltip Glutamate decarboxylase GABA-T Tooltip γ-Aminobutyrate aminotransferase
Other