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B141

Sigma-Aldrich

(±)-4-Bromohomoibotenic acid

solid

Synonym(s):

(±)-α-Amino-4-bromo-2,3-dihydro-3-oxo-5-isoxazolepropanoic acid

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About This Item

Empirical Formula (Hill Notation):
C6H7BrN2O4
CAS Number:
71366-32-0
Molecular Weight:
251.03
MDL number:
MFCD00153776
UNSPSC Code:
12352200
PubChem Substance ID:
329773184

form

solid

color

white

solubility

H2O: moderately soluble

SMILES string

NC(CC1=C(Br)C(=O)NO1)C(O)=O

InChI

1S/C6H7BrN2O4/c7-4-3(13-9-5(4)10)1-2(8)6(11)12/h2H,1,8H2,(H,9,10)(H,11,12)

InChI key

JRTOQOAGTSUNHA-UHFFFAOYSA-N

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Biochem/physiol Actions

Potent AMPA receptor agonist

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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J Arnt
Neuroscience letters, 23(3), 337-342 (1981-05-29)
Unilateral injection of AMPA ((R,S)-alpha-3-hydroxyl-5-methyl-4-isoxazolepropionic acid), 4-bromohomoibotenic acid, kainic acid and N-methylaspartic acid into the caudal part of substantia nigra induced ipsilateral turning behaviour. AMPA and kainic acid were most potent. Ibotenic acid produced short-lasting ipsilateral turning followed by long-lasting
D S Chung et al.
The Journal of pharmacology and experimental therapeutics, 283(2), 742-749 (1997-11-14)
Metabotropic glutamate receptors (mGluRs) are a family of glutamate receptors that are coupled to a variety of second messenger systems through GTP-binding proteins. Of the eight subtypes cloned to date, mGluR1 and mGluR5 are coupled to phosphoinositide hydrolysis in expression
U Madsen et al.
European journal of pharmacology, 230(3), 383-386 (1993-01-19)
The D-enantiomer of bromohomoibotenic acid (Br-HIBO) was inactive in electrophysiological experiments when administered alone, but enhanced depolarizations evoked by L-Br-HIBO or quisqualate when co-administered with these agonists. In addition, quisqualate induced a long-lasting (> 120 min) sensitization of cortical wedge
D S Chung et al.
Journal of neurochemistry, 63(1), 133-139 (1994-07-01)
Glutamate activates a family of receptors, known as metabotropic glutamate receptors (mGluRs), that are coupled to various second messenger systems through G proteins. All mGluR subtypes characterized to date in rat brain slices are activated by the glutamate analogue 1-aminocyclopentane-1S,3R-dicarboxylic
T Coquelle et al.
Neuroreport, 11(12), 2643-2648 (2000-09-08)
The lack of subtype-selective compounds for AMPA receptors (AMPA-R) led us to search for compounds with such selectivity. Homoibotenic acid analogues were investigated at recombinant GluR1o, GluR2o(R), GluR3o and GluR1o + 3o receptors expressed in Sf9 insect cells and affinities
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