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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Abbreviations
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CACA
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ChEMBL
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ChemSpider
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UNII
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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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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
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^ 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.
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^ 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.
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^ 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 |
GABAATooltip γ-Aminobutyric acid A receptor |
- Positive modulators (abridged; see
here for a full list):
α-EMTBL
-
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
-
Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal))
-
Topiramate
-
Valerian constituents (e.g.,
valerenic acid)
-
Volatiles/
gases (e.g.,
chloral hydrate,
chloroform,
diethyl ether,
paraldehyde,
sevoflurane)
- Negative modulators:
1,3M1B
-
3M2B
-
11-Ketoprogesterone
-
17-Phenylandrostenol
-
α3IA
-
α5IA (LS-193,268)
-
β-CCB
-
β-CCE
-
β-CCM
-
β-CCP
-
β-EMGBL
-
Anabolic steroids
-
Amiloride
-
Anisatin
-
β-Lactams (e.g.,
penicillins,
cephalosporins,
carbapenems)
-
Basmisanil
-
Bemegride
-
Bicyclic phosphates (
TBPS,
TBPO,
IPTBO)
-
BIDN
-
Bilobalide
-
Bupropion
-
CHEB
-
Chlorophenylsilatrane
-
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
-
Golexanolone
-
Iomazenil (123I)
-
IPTBO
-
Isopregnanolone (sepranolone)
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L-655,708
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Laudanosine
-
Lindane
-
MaxiPost
-
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)
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Pregnenolone sulfate
-
Propybicyphat
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PWZ-029
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Radequinil
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Ro 15-4513
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Ro 19-4603
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RO4882224
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RO4938581
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Sarmazenil
-
SCS
-
Suritozole
-
TB-21007
-
TBOB
-
TBPS
-
TCS-1105
-
Terbequinil
-
TETS
-
Thujone
-
U-93631
-
Zinc
-
ZK-93426
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GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor | |
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Metabotropic |
GABABTooltip γ-Aminobutyric acid B receptor | |
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