(Z)-4-Amino-2-butenoic acid

(Z)-4-Amino-2-butenoic acid[1] (CACA, cis-4-aminocrotonic acid) is a GABA receptor partial agonist selective for the GABAA-ρ (previously known as GABAC) subtype.[2][3][4]

(Z)-4-Amino-2-butenoic acid[1]
CACA molecule
Names
Preferred IUPAC name
(2Z)-4-Aminobut-2-enoic acid
Other names
(Z)-4-Amino-2-butenoic acid
cis-4-Aminocrotonic acid
4-Amino-cis-2-butenoic acid
Identifiers
3D model (JSmol)
Abbreviations CACA
ChEMBL
ChemSpider
UNII
  • InChI=1S/C4H7NO2/c5-3-1-2-4(6)7/h1-2H,3,5H2,(H,6,7)/b2-1- checkY
    Key: FMKJUUQOYOHLTF-UPHRSURJSA-N checkY
  • InChI=1/C4H7NO2/c5-3-1-2-4(6)7/h1-2H,3,5H2,(H,6,7)/b2-1-
    Key: FMKJUUQOYOHLTF-UPHRSURJBR
  • C(\C=C/C(=O)O)N
  • O=C(O)\C=C/CN
Properties
C4H7NO2
Molar mass 101.105 g·mol−1
124 mg/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

References
  1. cis-4-Aminocrotonic acid at Sigma-Aldrich
  2. Qian, H; Dowling, JE (1996). "Selective agonists for GABAC receptors". Trends in Neurosciences. 19 (5): 190. doi:10.1016/0166-2236(96)85451-8. PMID 8723205. S2CID 208792634.
  3. Duke, RK; Chebib, M; Balcar, VJ; Allan, RD; Mewett, KN; Johnston, GA (2000). "(+)- and (−)-cis-2-aminomethylcyclopropanecarboxylic acids show opposite pharmacology at recombinant rho(1) and rho(2) GABA(C) receptors". Journal of Neurochemistry. 75 (6): 2602–10. doi:10.1046/j.1471-4159.2000.0752602.x. PMID 11080214.
  4. Reis, GM; Duarte, ID (2007). "Involvement of chloride channel coupled GABA(C) receptors in the peripheral antinociceptive effect induced by GABA(C) receptor agonist cis-4-aminocrotonic acid". Life Sciences. 80 (14): 1268–73. doi:10.1016/j.lfs.2006.12.015. PMID 17316706.


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