(Z)-4-Amino-2-butenoic acid
(Z)-4-Amino-2-butenoic acid[1]
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Names |
IUPAC name
(Z)-4-Amino-2-butenoic acid |
Other names
cis-4-Aminocrotonic acid; 4-Amino-cis-2-butenoic acid |
Identifiers |
Abbreviations |
CACA |
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55199-25-2 N |
ChEMBL |
ChEMBL32307 Y |
ChemSpider |
5036011 Y |
InChI=1S/C4H7NO2/c5-3-1-2-4(6)7/h1-2H,3,5H2,(H,6,7)/b2-1- YKey: FMKJUUQOYOHLTF-UPHRSURJSA-N YInChI=1/C4H7NO2/c5-3-1-2-4(6)7/h1-2H,3,5H2,(H,6,7)/b2-1- Key: FMKJUUQOYOHLTF-UPHRSURJBR
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Jmol-3D images |
Image Image |
PubChem |
6603697 |
C(\C=C/C(=O)O)N O=C(O)\C=C/CN
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Properties |
Molecular formula |
C4H7NO2 |
Molar mass |
101.10 g·mol−1 |
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124 mg/mL |
Hazards |
S-phrases |
S22 S24/25 |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
N verify (what is: Y/N?) |
Infobox references |
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(Z)-4-Amino-2-butenoic acid (CACA, cis-4-aminocrotonic acid) is a GABA receptor partial agonist selective for the GABAA-ρ (previously known as GABAC) 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 |
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| Receptor (ligands) | |
- PAMs (abridged; see here for a full list): α-EMTBL
- Alcohols (e.g., ethanol)
- Avermectins (e.g., ivermectin)
- Barbiturates (e.g., phenobarbital)
- Benzodiazepines (e.g., diazepam)
- Bromide compounds (e.g., potassium bromide)
- Carbamates (e.g., meprobamate)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- Dihydroergolines (e.g., ergoloid (dihydroergotoxine))
- Etazepine
- Etifoxine
- Fenamates (e.g., mefenamic acid)
- Flavonoids (e.g., apigenin, hispidulin)
- Fluoxetine
- Flupirtine
- Imidazoles (e.g., etomidate)
- Kava constituents (e.g., kavain)
- Lanthanum
- Loreclezole
- Monastrol
- Neuroactive steroids (e.g., allopregnanolone, cholesterol)
- Niacin
- Nicotinamide (niacinamide)
- Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon))
- Norfluoxetine
- Petrichloral
- Phenols (e.g., propofol)
- Phenytoin
- Piperidinediones (e.g., glutethimide)
- Propanidid
- Pyrazolopyridines (e.g., etazolate)
- Quinazolinones (e.g., methaqualone)
- Retigabine (ezogabine)
- ROD-188
- Skullcap constituents (e.g., baicalin)
- Stiripentol
- Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
- Topiramate
- Valerian constituents (e.g., valerenic acid)
- Volatiles/gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane)
- NAMs: 1,3M1B
- 3M2B
- 17-Phenylandrostenol
- α5IA (LS-193,268)
- β-CCB
- β-CCE
- β-CCM
- β-CCP
- β-EMGBL
- Amiloride
- Anisatin
- β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
- Bemegride
- Bilobalide
- CHEB
- Cicutoxin
- Cloflubicyne
- Cyclothiazide
- DHEA
- DHEA-S
- Dieldrin
- (+)-DMBB
- DMCM
- DMPC
- EBOB
- Etbicyphat
- FG-7142 (ZK-31906)
- Fiproles (e.g., fipronil)
- Flavonoids (e.g., amentoflavone, oroxylin A)
- Flumazenil
- Fluoroquinolones (e.g., ciprofloxacin)
- Flurothyl
- Furosemide
- Iomazenil (123I)
- Isopregnanolone (sepranolone)
- L-655,708
- Laudanosine
- Leptazol
- Lindane
- MaxiPost
- Morphine
- Morphine-3-glucuronide
- MRK-016
- Naloxone
- Naltrexone
- Nicardipine
- Oenanthotoxin
- Pentetrazol (metrazol)
- Phenylsilatrane
- Picrotoxin (i.e., picrotin and picrotoxinin)
- Pregnenolone sulfate
- Propybicyphat
- PWZ-029
- Radequinil
- RG-1662
- Ro 15-4513
- Ro 19-4603
- RO4882224
- RO4938581
- Sarmazenil
- SCS
- Suritozole
- TB-21007
- TBOB
- TBPS
- TCS-1105
- Terbequinil
- TETS
- Thujone
- U-93631
- Zinc
- ZK-93426
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| Transporter (blockers) | |
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| Enzyme (inhibitors) | |
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| Others |
- Others: GABA-T activators: 3-Methyl-GABA
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| See also: GHBergics • Glutamatergics • Glycinergics |
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