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

(Z)-4-Amino-2-butenoic acid^[1]
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
CAS Number	55199-25-2 ;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	CACA
ChEMBL	ChEMBL32307 ;
ChemSpider	5036011 ;
IUPHAR/BPS	4148;
PubChem CID	6603697;
UNII	2B75NX3MA8 ;
	InChI InChI=1S/C4H7NO2/c5-3-1-2-4(6)7/h1-2H,3,5H2,(H,6,7)/b2-1- Key: FMKJUUQOYOHLTF-UPHRSURJSA-N ; InChI=1/C4H7NO2/c5-3-1-2-4(6)7/h1-2H,3,5H2,(H,6,7)/b2-1- Key: FMKJUUQOYOHLTF-UPHRSURJBR;
	SMILES C(\C=C/C(=O)O)N; O=C(O)\C=C/CN;
Properties
Chemical formula	C4H7NO2
Molar mass	101.105 g·mol−1
Solubility in water	124 mg/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

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

↑ ^1.0 ^1.1 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. 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.

{{Navbox | name = GABA receptor modulators | title = GABA receptor modulators | state = collapsed | bodyclass = hlist | groupstyle = text-align:center;

 | group1 = Ionotropic
 |  list1 = {{Navbox|subgroup
 | groupstyle = text-align:center
 | groupwidth = 5em

   | group1 = GABA_A
   | list1  =

Agonists: (+)-Catechin
Bamaluzole
Barbiturates (e.g., phenobarbital)
BL-1020
DAVA
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
Ibotenic acid
iso-THAZ
iso-THIP
Isoguvacine
Isomuscimol
Isonipecotic acid
Kojic amine
Lignans (e.g., honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g., allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
P4S
Progabide
Propofol
Quisqualamine
SL-75102
TACA
TAMP
Terpenoids (e.g., borneol)
Thiomuscimol
Tolgabide
ZAPA

Positive modulators (abridged; see here for a full list): α-EMTBL
Alcohols (e.g., ethanol)
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, [[Chemistry:Cholecholesterol]], THDOC)
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, [[Chemistry:Diethyl diethyl ether, Par paraldehyde]], sevoflurane)

Negative modulators: 1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
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)
L-655,708
Laudanosine
Leptazol
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalut enzalutamide, Chemistry:Flutamide|flut]]amide]], nilutamide)
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
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

   | group2 = GABA_A-ρ
   | list2  =

Negative modulators: 5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin, picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

}}

 | group2 = Metabotropic

| list2 =

 | below =

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

}}

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Original source: https://en.wikipedia.org/wiki/(Z)-4-Amino-2-butenoic acid. Read more

[SIGMA-1] 1.0 ^1.1 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.

[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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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
CAS Number	55199-25-2^Y
3D model (JSmol)	Interactive image Interactive image
Abbreviations	CACA
ChEMBL	ChEMBL32307^Y
ChemSpider	5036011^Y
IUPHAR/BPS	4148
PubChem CID	6603697
UNII	2B75NX3MA8^Y
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
SMILES C(\C=C/C(=O)O)N O=C(O)\C=C/CN
Properties
Chemical formula	C₄H₇NO₂
Molar mass	101.105 g·mol⁻¹
Solubility in water	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 ^YN ?)
Infobox references

Anonymous

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