121313-14-2

Basic information

• Product Name: (R)-4-BROMO-HOMO-IBOTENIC ACID
• Synonyms: (R)-ALPHA-AMINO-4-BROMO-3-HYDROXY-5-ISOXAZOLEPROPIONIC ACID;(R)-4-BROMO-HOMO-IBOTENIC ACID;(R)-A-AMINO-4-BROMO-3-HYDROXY-5-ISOXAZOLEPROPIONIC ACID;(R)-4-BROMO-HOMO-IBOTENIC ACID, >98%
• CAS NO: 121313-14-2
• Molecular Formula: C5H5BrN2O4
• Molecular Weight: 237.01
• Mol File: 121313-14-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.95g/cm³
• Refractive Index: 1.651
• CAS DataBase Reference: (R)-4-BROMO-HOMO-IBOTENIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-BROMO-HOMO-IBOTENIC ACID(121313-14-2)
• EPA Substance Registry System: (R)-4-BROMO-HOMO-IBOTENIC ACID(121313-14-2)

Safety Data

• Hazardous Substances Data: 121313-14-2(Hazardous Substances Data)

Usage

General Description

(R)-4-Bromo-Homo-Ibotenic Acid is a chemical compound that belongs to the class of ibotenic acid derivatives. It is an analog of the neurotransmitter glutamate and acts as a potent agonist at glutamate receptors. (R)-4-BROMO-HOMO-IBOTENIC ACID is used in research to study the role of glutamate receptors in various physiological and pathological processes in the brain. It has been found to exhibit neuroexcitatory and neurotoxic effects, and has potential applications in the study of neurodegenerative disorders and drug development. Additionally, (R)-4-Bromo-Homo-Ibotenic Acid may also have potential utility in understanding the mechanisms underlying the effects of psychoactive substances.

InChI:InChI=1/C5H5BrN2O4/c6-1-3(2(7)5(10)11)12-8-4(1)9/h2H,7H2,(H,8,9)(H,10,11)/t2-/m1/s1

Upstream product

• 121253-50-7 (RS)-α-amino-4-bromo-3-methoxy-5-isoxazolepropionic acid 
• 71366-31-9 diethyl acetamido<(4-bromo-3-methoxyisoxazol-5-yl)methyl>malonate 
• 121313-17-5 (R)-α-(acetylamino)-4-bromo-3-methoxy-5-isoxazolepropionic acid 

Relevant articles and documents

Excitatory amino acid agonists. Enzymic resolution, X-ray structure, and enantioselective activities of (R)- and (S)-bromohomoibotenic acid

The enantiomers of α-amino-4-bromo-3-hydroxy-5-isoxazolepropionic acid (4-bromohomoibotenic acid, Br-HIBO, 1), a selective and potent agonist at one class of the central (S)-glutamic acid receptors, were prepared with an enantiomeric excess higher than 98.8% via stereoselective enzymic hydrolysis of (RS)-α-(acetylamino)-4-bromo-3-methoxy-5-isoxazolepropionic acid using immobilized aminoacylase. The absolute configuration of the enantiomers of Br-HIBO was established by X-ray crystallographic analysis, which confirmed the expected preference of the enzyme for the S form of the substrate. (S)- and (RS)-Br-HIBO were potent neuroexcitants on cat spinal neurones in vivo, while (R)-Br-HIBO was a very weak excitant. Correspondingly, the S enantiomer of Br-HIBO (IC50 = 0.34 μM) was considerably more potent than the R form (IC50 = 32 μM) as an inhibitor of [3H]-(RS)-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid ([3H]AMPA) binding to rat brain synaptic membranes in vitro. In contrast, (S)- and (R)-Br-HIBO were approximately equipotent (IC50 values of 0.22 and 0.15 μM, respectively) as inhibitors of [3H]-(S)-glutamic acid binding in the presence of CaCl2. The enantiomers of Br-HIBO showed no significant affinity for those binding sites on rat brain membranes which are labeled by [3H]kainic acid or [3H]-(R)-aspartic acid.