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

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(Z)-4-Amino-2-butenoic acid^[1]


IUPAC name (Z)-4-Amino-2-butenoic acid
Other names cis-4-Aminocrotonic acid; 4-Amino-cis-2-butenoic acid
Identifiers
Abbreviations	CACA
CAS number	55199-25-2
PubChem	6603697
ChemSpider	5036011^Y
ChEMBL	CHEMBL32307^Y
Jmol-3D images	Image 1 Image 2
SMILES C(\C=C/C(=O)O)N O=C(O)\C=C/CN
InChI InChI=1S/C4H7NO2/c5-3-1-2-4(6)7/h1-2H,3,5H2,(H,6,7)/b2-1-^Y Key: FMKJUUQOYOHLTF-UPHRSURJSA-N^Y InChI=1/C4H7NO2/c5-3-1-2-4(6)7/h1-2H,3,5H2,(H,6,7)/b2-1- Key: FMKJUUQOYOHLTF-UPHRSURJBR
Properties
Molecular formula	C₄H₇NO₂
Molar mass	101.10 g mol⁻¹
Solubility in water	124 mg/mL
Hazards
S-phrases	S22 S24/25
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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

References

↑ cis-4-Aminocrotonic acid at Sigma-Aldrich
↑ 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.
↑ 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. PMID 11080214.
↑ 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.

GABAergics

Receptor
ligands

GABA_A	Agonists: Main site: Bamaluzole Gaboxadol Ibotenic acid Isoguvacine Isonipecotic acid Muscimol (Amanita Muscaria) Progabide SL 75102 Thiomuscimol Tolgabide; Positive allosteric modulators: Alcohols (2M2B, Ethanol, Ethchlorvynol, Methylpentynol Barbiturates Benzodiazepines Carbamates Chlormezanone Clomethiazole Etomidate Kavalactones (Kava) Loreclezole Metomidate Neuroactive steroids Nonbenzodiazepines (β-Carbolines, Cyclopyrrolones, Imidazopyridines, Pyrazolopyrimidines, etc.) Phenols Piperidinediones Propanidid Pyrazolopyridines Quinazolinones ROD-188 Skullcap Stiripentol Valerenic acid (Valerian) Note: See the GABA_A receptor PAMs navbox for a full list of GABA_A positive allosteric modulators. Antagonists: Main site: Bicuculline Gabazine Pitrazepin Quisqualamine; Negative allosteric modulators: 17-Phenylandrostenol (17-PA) α5IA Bilobalide Cicutoxin Cyclothiazide DMCM Flumazenil Flurothyl Furosemide Iomazenil (¹²³I) L-655,708 Oenanthotoxin Penicillin Pentylenetetrazol Picrotoxin PWZ-029 Radequinil Ro15-4513 Sarmazenil Suritozole Terbequinil Thujone Thiocolchicoside ZK-93426

GABA_B	Agonists: Main site: 1,4-Butanediol Baclofen GBL GHB GHV GVL Lesogaberan Phenibut Progabide SKF-97,541 Tolgabide; Positive allosteric modulators: BHF-177 BHFF BSPP CGP-7930 GS-39783 Antagonists: Main site: CGP-35348 Phaclofen Saclofen SCH-50911

GABA_C	Agonists: Main site: CACA CAMP GABOB N⁴-Chloroacetylcytosine arabinoside Progabide Tolgabide Antagonists: Main site: Bilobalide TPMPA

Reuptake
inhibitors

Plasmalemmal

GAT inhibitors	CI-966 Deramciclane EF-1502 Gabaculine Guvacine Nipecotic acid NNC 05-2090 SKF-89976A SNAP-5114 Tiagabine

Enzyme
inhibitors

Anabolism

GAD inhibitors	Allylglycine

Catabolism

GABA-T inhibitors	3-Hydrazinopropionic acid Aminooxyacetic acid Gabaculine Isoniazid Phenelzine Phenylethylidenehydrazine Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (Divalproex sodium) Valproic acid Valpromide Vigabatrin

Others

Precursors	Glutamate Glutamine

Cofactors	Vitamin B₆ (pyridoxine pyridoxamine pyridoxal phosphate)

Others	Gabapentin Hopantenic acid Picamilon Pregabalin L-Theanine

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