From Wikipedia, the free encyclopedia
(Z)-4-Amino-2-butenoic acid[1]
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Names
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Preferred IUPAC name
(2Z)-4-Aminobut-2-enoic acid
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Other names
(Z)-4-Amino-2-butenoic acid cis-4-Aminocrotonic acid 4-Amino-cis-2-butenoic acid
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Identifiers
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3D model (JSmol)
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Abbreviations
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CACA
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ChEMBL
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ChemSpider
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IUPHAR/BPS
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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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C(\C=C/C(=O)O)N O=C(O)\C=C/CN
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Properties
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C4H7NO2
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Molar mass
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101.105 g·mol−1
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124 mg/mL
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N (what is Y N ?)
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Infobox references
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Chemical compound
(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]
References[]
- ^ a b 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. S2CID 208792634.
- ^ 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.
- ^ 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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Ionotropic | GABAA |
- Positive modulators (abridged; see here for a full list):
- Alcohols (e.g., drinking alcohol, 2M2B)
- Anabolic steroids
- 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, THDOC)
- Niacin
- 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
- (e.g., sulfonmethane (sulfonal))
- Topiramate
- Valerian constituents (e.g., valerenic acid)
- Volatiles/gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane)
- Negative modulators:
- 11-Ketoprogesterone
- 17-Phenylandrostenol
- α5IA (LS-193,268)
- Anabolic steroids
- Amiloride
- Anisatin
- β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
- Basmisanil
- Bemegride
- Bicyclic phosphates (TBPS, TBPO, IPTBO)
- BIDN
- Bilobalide
- Bupropion
- Chlorophenylsilatrane
- Cicutoxin
- Cloflubicyne
- Cyclothiazide
- DHEA
- DHEA-S
- Dieldrin
- DMCM
- EBOB
- FG-7142 (ZK-31906)
- (e.g., fipronil)
- Flavonoids (e.g., amentoflavone, oroxylin A)
- Flumazenil
- Fluoroquinolones (e.g., ciprofloxacin)
- Flurothyl
- Furosemide
- Golexanolone
- Iomazenil (123I)
- IPTBO
- Isopregnanolone (sepranolone)
- L-655,708
- Laudanosine
- Lindane
- Morphine
- Morphine-3-glucuronide
- MRK-016
- Naloxone
- Naltrexone
- Nicardipine
- Nonsteroidal antiandrogens (e.g., apalutamide, bicalutamide, enzalutamide, flutamide, nilutamide)
- Oenanthotoxin
- Pentylenetetrazol (pentetrazol)
- Phenylsilatrane
- Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
- Pregnenolone sulfate
- PWZ-029
- Radequinil
- Ro 15-4513
- Sarmazenil
- Suritozole
- TB-21007
- TBPS
- Terbequinil
- TETS
- Thujone
- Zinc
- ZK-93426
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GABAA-ρ | |
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Metabotropic | |
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- See also
- Receptor/signaling modulators
- GABAA receptor positive modulators
- GABA metabolism/transport modulators
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Categories:
- Amino acids
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- GABAA-rho receptor agonists
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