γ-Acetylenic GABA

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γ-Acetylenic GABA^[1]
Names

IUPAC name 4-Aminohex-5-ynoic acid
Other names 4-Amino-5-hexynoic acid
Identifiers
CAS Number	57659-38-8^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL330129
ChemSpider	3334
ECHA InfoCard	100.165.059
EC Number	637-345-7
PubChem CID	3452
UNII	PG9G3XCD6P
CompTox Dashboard (EPA)	DTXSID40973249
InChI InChI=1S/C6H9NO2/c1-2-5(7)3-4-6(8)9/h1,5H,3-4,7H2,(H,8,9) Key: BJNIHWSOVCDBHS-UHFFFAOYSA-N
SMILES C#CC(CCC(=O)O)N
Properties
Chemical formula	C₆H₉NO₂
Molar mass	127.143 g·mol⁻¹
Hazards
GHS labelling:^[2]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

γ-Acetylenic GABA, also known as 4-amino-5-hexynoic 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.

GABA metabolism and transport modulators

Transporter

GATTooltip GABA transporter	Inhibitors: 4-Aminovaleric acid 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 SKF-89976A SNAP-5114 TACA Tiagabine
VIAATTooltip Vesicular inhibitory amino acid transporter	Inhibitors: β-Alanine Bafilomycin A1 Chicago sky blue 6B Evans blue GABA Glycine N-Butyric acid Nigericin Nipecotic acid Valinomycin Vigabatrin

Enzyme

GADTooltip Glutamate decarboxylase	Inhibitors: 3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide Activators: 3-Methyl-GABA
GABA-TTooltip γ-Aminobutyrate aminotransferase	Inhibitors: 3-Hydrazinopropionic acid DABA γ-Acetylenic-GABA AOAA EOS Gabaculine Isoniazid L-Cycloserine Phenelzine PEH Rosmarinic acid (lemon balm) Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (divalproex sodium) Valproic acid Valpromide Vigabatrin Activators: 3-Methyl-GABA

Other

Antivitamin B6	Ginkgotoxin

See also: Receptor/signaling modulators; GABA receptor modulators; GABA_A receptor positive modulators; Glutamate metabolism/transport modulators

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