2,4-Diaminobutyric acid

2,4-Diaminobutyric acid
Names
IUPAC name
2,4-diaminobutanoic acid
Other names
α,γ-diaminobutanoic acid
Identifiers
CAS Number
  • 305-62-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:64307
ChEMBL
  • ChEMBL307931
ChemSpider
  • 457
EC Number
  • 206-166-2
PubChem CID
  • 470
UNII
  • 92V7KM11ZK
CompTox Dashboard (EPA)
  • DTXSID20938710 Edit this at Wikidata
InChI
  • Key: OGNSCSPNOLGXSM-UHFFFAOYSA-N
  • InChI=1S/C4H10N2O2/c5-2-1-3(6)4(7)8/h3H,1-2,5-6H2,(H,7,8)
  • C(CN)C(C(=O)O)N
Properties
Chemical formula
 C4H10N2O2
Molar mass 118.136 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

2,4-Diaminobutyric acid, also known as DABA, is GABA-T non-competitive inhibitor and a GABA reuptake inhibitor.

Mechanism of action

DABA's main action is being an inhibitor of GABA transaminase, an enzyme that converts GABA back to glutamate. When the enzyme is inhibited, this conversion cannot happen, therefore, GABA levels are elevated.[1]

It has also been observed that 2,4-diaminobutyric acid is a GABA reuptake inhibitor.[2] This action further elevates levels of GABA.

Toxicity

In addition to being a neurotoxin, DABA can also cause liver damage.

Its potential as an anticonvulsant is unclear, it has been shown to have anticonvulsant properties against picrotoxin, but over the long term, it could paradoxically cause convulsions.[2][3]

References

  1. ^ Beart, P.M.; Bilal, Khalidah (1977). "L-2,4-Diaminobutyric acid and the GABA system". Neuroscience Letters. 5 (3–4): 193–198. doi:10.1016/0304-3940(77)90046-5. PMID 19604993. S2CID 34289803.
  2. ^ a b Taberner, P. V.; Pycock, C. J. (1981). "The Effects of GABA Uptake Inhibitors including 2, 4-Diaminobutyric Acid on GABA Metabolism in vivo". Central Neurotransmitter Turnover. pp. 177–182. doi:10.1007/978-1-4615-9778-0_12. ISBN 978-1-4615-9780-3.
  3. ^ O'Neal, R. M.; Chen, C. H.; Reynolds, C. S.; Meghal, S. K.; Koeppe, R. E. (1968). "The 'neurotoxicity' of L-2,4-diaminobutyric acid". The Biochemical Journal. 106 (3): 699–706. doi:10.1042/bj1060699. PMC 1198561. PMID 5639925.
  • v
  • t
  • e
GABATooltip γ-Aminobutyric acid metabolism and transport modulators
Transporter
GATTooltip GABA transporter
VIAATTooltip Vesicular inhibitory amino acid transporter
Enzyme
GADTooltip Glutamate decarboxylase
GABA-TTooltip γ-Aminobutyrate aminotransferase
Other
Antivitamin B6
See also
Receptor/signaling modulators
GABA receptor modulators
GABAA receptor positive modulators
Glutamate metabolism/transport modulators