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ibotenic acid
4-isoxazoline-5-acetic acid, alpha-amino-3-oxo-

Supplier Sponsors

Name:2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid
CAS Number: 2552-55-8Picture of molecule3D/inchi
Other(deleted CASRN):31758-99-3
FDA UNII: 44AS82FRSI
Nikkaji Web:J7.613I
MDL:MFCD00069294
XlogP3-AA:-3.90 (est)
Molecular Weight:158.11362000
Formula:C5 H6 N2 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:toxic natural substances
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 458.80 °C. @ 760.00 mm Hg (est)
Flash Point: 448.00 °F. TCC ( 231.30 °C. ) (est)
logP (o/w): -1.070 (est)
Soluble in:
 water, 3.776e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Ibotenic acid ≥98%
Odor: characteristic
Use: Ibotenic acid is a neuroexcitatory amino acid originally isolated from amanita
Carbosynth
For experimental / research use only.
Ibotenic Acid
EMD Millipore
For experimental / research use only.
Ibotenic Acid
sds
ExtraSynthese
For experimental / research use only.
Ibotenic Acid
Santa Cruz Biotechnology
For experimental / research use only.
Ibotenic Acid ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Ibotenic Acid ∼95%, solid
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-mouse LD50 15 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 311, 1968.

oral-mouse LD50 38 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 311, 1968.

intravenous-rat LD50 42 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 311, 1968.

oral-rat LD50 129 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 311, 1968.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
toxic natural substances
Recommendation for ibotenic acid usage levels up to:
 not for fragrance use.
 
Recommendation for ibotenic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :1233
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid
Chemidplus:0002552558
RTECS:NY2100000 for cas# 2552-55-8
 
References:
 2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):1233
Pubchem (sid):134982726
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10600
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid
alpha-amino-2,3-dihydro-3-oxo-5-isoxazoleacetic acid
 ibotenate
dextro,laevo-ibotenic acid
DL-ibotenic acid
4-isoxazoline-5-acetic acid, alpha-amino-3-oxo-
 

Articles:

PubMed:Enhanced consumption of salient solutions following pedunculopontine tegmental lesions.
PubMed:Fungal hallucinogens psilocin, ibotenic acid, and muscimol: analytical methods and biologic activities.
PubMed:Basolateral amygdala lesions facilitate reward choices after negative feedback in rats.
PubMed:Neonatal hippocampal damage impairs specific food/place associations in adult macaques.
PubMed:Hippocampus-dependent place learning enables spatial flexibility in C57BL6/N mice.
PubMed:Bilateral lesions of the thalamic trigeminal orosensory area dissociate natural from drug reward in contrast paradigms.
PubMed:Prefrontal dopamine release and sensory-specific satiety altered in rats with neonatal ventral hippocampal lesions.
PubMed:Berberine promotes axonal regeneration in injured nerves of the peripheral nervous system.
PubMed:Amygdala central nucleus interacts with dorsolateral striatum to regulate the acquisition of habits.
PubMed:Superior colliculus lesions impair threat responsiveness in infant capuchin monkeys.
PubMed:Evidence for time-of-day dependent effect of neurotoxic dorsomedial hypothalamic lesions on food anticipatory circadian rhythms in rats.
PubMed:Dissociable effects of subtotal lesions within the macaque orbital prefrontal cortex on reward-guided behavior.
PubMed:Pontine and thalamic influences on fluid rewards: III. Anticipatory contrast for sucrose and corn oil.
PubMed:Deconstructing craving: dissociable cortical control of cue reactivity in nicotine addiction.
PubMed:Neonatal amygdala lesions alter responsiveness to objects in juvenile macaques.
PubMed:Selective lesions of the dorsomedial striatum impair serial spatial reversal learning in rats.
PubMed:Distinct contributions of the amygdala and hippocampus to fear expression.
PubMed:Functional interaction of medial mediodorsal thalamic nucleus but not nucleus accumbens with amygdala and orbital prefrontal cortex is essential for adaptive response selection after reinforcer devaluation.
PubMed:Antidepressant-like effects of medial prefrontal cortex deep brain stimulation in rats.
PubMed:Chemotherapy-induced kaolin intake is increased by lesion of the lateral parabrachial nucleus of the rat.
PubMed:Bar pressing for food: differential consequences of lesions to the anterior versus posterior pedunculopontine.
PubMed:Gustatory insular cortex lesions disrupt drug-induced, but not lithium chloride-induced, suppression of conditioned stimulus intake.
PubMed:A comparison of behavioural and histological outcomes of periventricular injection of ibotenic acid in neonatal rats at postnatal days 5 and 7.
PubMed:Effects of motor training on the recovery of manual dexterity after primary motor cortex lesion in macaque monkeys.
PubMed:Neurotoxic lesions of the medial mediodorsal nucleus of the thalamus disrupt reinforcer devaluation effects in rhesus monkeys.
PubMed:Lesions of the basal forebrain impair reversal learning but not shifting of attentional set in rats.
PubMed:Insular cortex lesions fail to block flavor and taste preference learning in rats.
PubMed:Neurotoxic lesions of the caudate-putamen on a reaching for food task in the rat: acute sensorimotor neglect and chronic qualitative motor impairment follow lateral lesions and improved success follows medial lesions.
PubMed:The expression of social dominance following neonatal lesions of the amygdala or hippocampus in rhesus monkeys (Macaca mulatta).
PubMed:Hippocampal lesion prevents spatial relational learning in adult macaque monkeys.
PubMed:The role of the dorsal CA3 hippocampal subregion in spatial working memory and pattern separation.
PubMed:Specific changes in conditioned responding following neurotoxic damage to the posterior parietal cortex.
PubMed:Medial parabrachial nucleus neurons modulate d-fenfluramine-induced anorexia through 5HT2C receptors.
PubMed:Differential effects of infralimbic cortical lesions on temperature and locomotor activity responses to feeding in rats.
PubMed:Behavioral and morphological alterations following neonatal excitotoxic lesions of the medial prefrontal cortex in rats.
PubMed:Dipsogenic stimulation in ibotenic DRN-lesioned rats induces concomitant sodium appetite.
PubMed:Role of gustatory thalamus in anticipation and comparison of rewards over time in rats.
PubMed:An examination of d-amphetamine self-administration in pedunculopontine tegmental nucleus-lesioned rats.
PubMed:Combined unilateral lesions of the amygdala and orbital prefrontal cortex impair affective processing in rhesus monkeys.
PubMed:Effects of hippocampal lesions in a food location task in pigeons.
PubMed:Learning and memory impairments in Kv beta 1.1-null mutants are rescued by environmental enrichment or ageing.
PubMed:Potent mammalian cerebroprotection and neuronal cell death inhibition are afforded by a synthetic antioxidant analogue of marine invertebrate cell protectant ovothiols.
PubMed:Lateral hypothalamic lesions impair flavour-nutrient and flavour-toxin trace learning in rats.
PubMed:An examination of the effects of bilateral excitotoxic lesions of the pedunculopontine tegmental nucleus on responding to sucrose reward.
PubMed:Protection and reversal of excitotoxic neuronal damage by glucagon-like peptide-1 and exendin-4.
PubMed:Medial versus lateral parabrachial nucleus lesions in the rat: effects on mercaptoacetate-induced feeding and conditioned taste aversion.
PubMed:The effect of excitotoxic lesions of the pedunculopontine tegmental nucleus on performance of a progressive ratio schedule of reinforcement.
PubMed:Anterograde amnesia and temporally graded retrograde amnesia for a nonspatial memory task after lesions of hippocampus and subiculum.
PubMed:The effects of excitotoxic lesions of the pedunculopontine tegmental nucleus on conditioned place preference to 4%, 12% and 20% sucrose solutions.
PubMed:Persistence of meal-entrained circadian rhythms following area postrema lesions in the rat.
PubMed:Parabrachial nucleus lesions block taste and attenuate flavor preference and aversion conditioning in rats.
PubMed:Conditioned flavor preference and aversion: role of the lateral hypothalamus.
PubMed:Medial versus lateral parabrachial nucleus lesions in the rat: effects on cholecystokinin- and D-fenfluramine-induced anorexia.
PubMed:The function of the pedunculopontine nucleus in the preparation and execution of an externally-cued bar pressing task in the rat.
PubMed:Increased alcohol intake and behavioral disinhibition in rats with ventral striatal neuron loss.
PubMed:Combined lesions of hippocampus and subiculum Do not produce deficits in a nonspatial social olfactory memory task.
PubMed:Lateral parabrachial nucleus lesions in the rat: aversive and appetitive gustatory conditioning.
PubMed:Medial frontal cortex mediates perceptual attentional set shifting in the rat.
PubMed:Feeding-entrained circadian rhythms are attenuated by lesions of the parabrachial region in rats.
PubMed:The paraventricular nucleus of the thalamus alters rhythms in core temperature and energy balance in a state-dependent manner.
PubMed:Hippocampectomized rats are impaired in homing by path integration.
PubMed:Effects of dorsomedial hypothalamic nuclei lesions on intake of an imbalanced amino acid diet.
PubMed:Behavioral disinhibition following basal forebrain excitotoxin lesions: alcohol consumption, defensive aggression, impulsivity and serotonin levels.
PubMed:Differential effects of dorsal and ventral hippocampal lesions.
PubMed:Paw and limb use in skilled and spontaneous reaching after pyramidal tract, red nucleus and combined lesions in the rat: behavioral and anatomical dissociations.
PubMed:Neurotoxic hippocampal lesions fail to impair reinstatement of an appetitively conditioned response.
PubMed:Increase of the aversive value of taste stimuli following ibotenic acid lesion of the central amygdaloid nucleus in the rat.
PubMed:Discrete thalamic lesions attenuate winter adaptations and increase body weight.
PubMed:The role of an amygdalo-nigrostriatal pathway in associative learning.
PubMed:Hippocampal tissue transplants reverse lesion-induced spatial memory deficits in zebra finches (Taeniopygia guttata).
PubMed:Ventromedial nuclei of the hypothalamus are involved in the phase advance of temperature and activity rhythms in food-restricted rats fed during daytime.
PubMed:The hypothalamic ventromedial nuclei couple activity in the hypothalamo-pituitary-adrenal axis to the morning fed or fasted state.
PubMed:Ibotenic acid lesions of the amygdala basolateral complex or central nucleus differentially effect the response to reductions in reward.
PubMed:The hippocampus and reward: effects of hippocampal lesions on progressive-ratio responding.
PubMed:An animal model for type 2 alcoholism? Alcohol consumption and aggressive behavior following lesions in the raphe nuclei, medial hypothalamus, or ventral striatum-septal area.
PubMed:The nucleus accumbens in monkeys (Macaca fascicularis): II. Emotion and motivation.
PubMed:Does the red nucleus provide the tonic support against which fractionated movements occur? A study on forepaw movements used in skilled reaching by the rat.
PubMed:Effects of nerve growth factor treatment on rats with lesions of the nucleus basalis magnocellularis produced by ibotenic acid, quisqualic acid, and AMPA.
PubMed:The effects of bilateral striatal lesions on the acquisition of an operant test of short term memory.
PubMed:In a rat model of parkinsonism, lesions of the subthalamic nucleus reverse increases of reaction time but induce a dramatic premature responding deficit.
PubMed:Central nucleus of the amygdala and the development of hypertension in spontaneously hypertensive rats.
PubMed:The effects of mammillary body lesions on delayed matching and delayed non-matching to place tasks in the mice.
PubMed:Selective damage to the hippocampal region blocks long-term retention of a natural and nonspatial stimulus-stimulus association.
PubMed:Effects of ibotenic acid lesions of the nucleus accumbens on instrumental action.
PubMed:Effects of morphine injection into the parabrachial area on saccharin preference: modulation by lateral hypothalamic neurons.
PubMed:The nucleus accumbens in monkeys (Macaca fascicularis): I. The organization of behaviour.
PubMed:Reversal of dexfenfluramine-induced anorexia and c-Fos/c-Jun expression by lesion in the lateral parabrachial nucleus.
PubMed:An investigation into the role of the pedunculopontine tegmental nucleus in the mediation of locomotion and orofacial stereotypy induced by d-amphetamine and apomorphine in the rat.
PubMed:Ibotenate lesions of the hippocampus enhance latent inhibition in conditioned taste aversion and increase resistance to extinction in conditioned taste preference.
PubMed:Lateral parabrachial subnucleus lesions abolish feeding induced by mercaptoacetate but not by 2-deoxy-D-glucose.
PubMed:Where does damage lead to enhanced food aversion: the ventral pallidum/substantia innominata or lateral hypothalamus?
PubMed:Two types of motivation revealed by ibotenic acid nucleus accumbens lesions: dissociation of food carrying and hoarding and the role of primary and incentive motivation.
PubMed:Lateral hypothalamic injections of glutamate, kainic acid, D,L-alpha-amino-3-hydroxy-5-methyl-isoxazole propionic acid or N-methyl-D-aspartic acid rapidly elicit intense transient eating in rats.
PubMed:Effects of NBM lesions with two neurotoxins on spatial memory and autoshaping.
PubMed:Comparison of the effects of single and combined neurotoxic lesions of the nucleus basalis magnocellularis and dorsal noradrenergic bundle on learning and memory in the rat.
PubMed:Naturally-occurring excitatory amino acids as neurotoxins and leads in drug design.
PubMed:Drug discrimination learning in rats with excitotoxic lesions of nucleus basalis and ventral globus pallidus.
PubMed:Excitotoxic lesions of the pedunculopontine tegmental nucleus of the rat. II. Examination of eating and drinking, rotation, and reaching and grasping following unilateral ibotenate or quinolinate lesions.
PubMed:Excitotoxicity in the embryonic chick spinal cord.
PubMed:Differential involvement of anterior and posterior cingulate cortices in spatial discriminative learning in a T-maze in mice.
PubMed:Red nucleus lesions do not affect limb preference or use, but exacerbate the effects of motor cortex lesions on grasping in the rat.
PubMed:Ibotenic acid lesion of the lateral hypothalamus increases preference and aversion thresholds for saccharin and alters the morphine modulation of taste.
PubMed:Comparative effects of ibotenic acid- and quisqualic acid-induced lesions of the substantia innominata on attentional function in the rat: further implications for the role of the cholinergic neurons of the nucleus basalis in cognitive processes.
PubMed:Effects of anterior or dorsomedial thalamic ibotenic lesions on learning and memory in rats.
PubMed:Ibotenate-induced total septal lesions reduce resistance to extinction but spare the partial reinforcement extinction effect in the rat.
PubMed:Lateral hypothalamic feeding mechanisms: iontophoretic effects of kainic acid, ibotenic acid and 6-hydroxydopamine.
PubMed:Striatal grafts in rats with unilateral neostriatal lesions--III. Recovery from dopamine-dependent motor asymmetry and deficits in skilled paw reaching.
PubMed:Double dissociations of the effects of amygdala and insular cortex lesions on conditioned taste aversion, passive avoidance, and neophobia in the rat using the excitotoxin ibotenic acid.
PubMed:Effect of bilateral ibotenic acid lesions in the basolateral amygdala on the sham feeding response to sucrose in the rat.
PubMed:The effects of intra-subicular ibotenate on resistance to extinction after continuous or partial reinforcement.
PubMed:Locomotor behavior changes induced by E-17 striatal transplants in normal rats.
PubMed:Comparative functions of the central noradrenergic, dopaminergic and cholinergic systems.
PubMed:Ingestive behavior of rats with ibotenic acid lesions of the dorsomedial hypothalamus.
PubMed:Visual localization and discrimination after ibotenic lesion of the cat orbito-insular cortex.
PubMed:Pilocarpine and physostigmine attenuate spatial memory impairments produced by lesions of the nucleus basalis magnocellularis.
PubMed:The effects of intrahippocampal ibotenate on resistance to extinction after continuous or partial reinforcement.
PubMed:Differential effects of neurotoxic lesions on psychoneuroendocrine functions.
PubMed:Disruption of central cholinergic systems in the rat by basal forebrain lesions or atropine: effects on feeding, sensorimotor behaviour, locomotor activity and spatial navigation.
PubMed:Learning and memory deficits after lesions of the nucleus basalis magnocellularis: reversal by physostigmine.
PubMed:Comparison of electrolytic and ibotenic acid lesions in the lateral hypothalamus.
PubMed:Ibotenic acid lesions of the lateral hypothalamus: comparison with the electrolytic lesion syndrome.
 
Notes:
a neurotoxic isoxazole (similar to kainic acid and muscimol) found in amanita mushrooms. it causes motor depression, ataxia, and changes in mood, perceptions and feelings, and is a potent excitatory amino acid agonist.
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