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Merck
CN

B141

(±)-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
UNSPSC Code:
12352200
PubChem Substance ID:
329773184
MDL number:
MFCD00153776

Key Documents

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Product Name

(±)-4-Bromohomoibotenic acid, solid

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)

SMILES string

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

InChI key

JRTOQOAGTSUNHA-UHFFFAOYSA-N

form

solid

color

white

solubility

H2O: moderately soluble

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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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
Mai Marie Holm et al.
Proceedings of the National Academy of Sciences of the United States of America, 102(34), 12053-12058 (2005-08-16)
Glutamate receptors (GluRs) are the most abundant mediators of the fast excitatory neurotransmission in the human brain. Agonists will, after activation of the receptors, induce different degrees of desensitization. The efficacy of agonists strongly correlates with the agonist-induced closure of
T G Banke et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 21(9), 3052-3062 (2001-04-20)
Although GluR1(o) and GluR3(o) are homologous at the amino acid level, GluR3(o) desensitizes approximately threefold faster than GluR1(o). By creating chimeras of GluR1(o) and GluR3(o) and point amino acid exchanges in their S2 regions, two residues were identified to be
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
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