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2,4-Diaminobutyric acid

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2,4-Diaminobutyric acid
2,4-Diaminobutyric acid.svg
2-4-Diaminobutyric-acid Conformer3D large.png
Names
Preferred IUPAC name
2,4-Diaminobutanoic acid
Other names
α,γ-diaminobutanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.607 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-166-2
PubChem CID
UNII
  • 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
C4H10N2O2
Molar mass 118.136 g·mol−1
Pharmacology
Drug class GABA-T inhibitor; GABA reuptake inhibitor
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 PM, Bilal K (July 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. 1 2 Taberner PV, Pycock CJ (1981). "The Effects of GABA Uptake Inhibitors including 2, 4-Diaminobutyric Acid on GABA Metabolism in vivo". In Pycock CJ, Taberner PV (eds.). Central Neurotransmitter Turnover. pp. 177–182. doi:10.1007/978-1-4615-9778-0_12. ISBN   978-1-4615-9780-3.
  3. ↑ O'Neal RM, Chen CH, Reynolds CS, Meghal SK, Koeppe RE (February 1968). "The 'neurotoxicity' of L-2,4-diaminobutyric acid". The Biochemical Journal. 106 (3): 699–706. doi:10.1042/bj1060699. PMC   1198561 . PMID   5639925.
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