Ibotenic acid

Names

[ Name ]:
Ibotenic acid

[Synonym ]:
Ibotenic acid
5-Isoxazoleacetic acid, α-amino-2,3-dihydro-3-oxo-
a-Amino-3-hydroxy-5-isoxazoleacetic Acid
a-Amino-2,3-dihydro-3-oxo-5-isoxazoleacetic Acid
Acide amino(3-oxo-2,3-dihydro-1,2-oxazol-5-yl)acétique
Amino(3-oxo-2,3-dihydro-1,2-oxazol-5-yl)acetic acid
MFCD00069294
Amino-(3-hydroxy-5-isoxazolyl)acetic acid
2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid

Biological Activity

[Description]:

Ibotenic acid has agonist activity at both the N-methyl-D-aspartate (NMDA) and trans-ACPD or metabolotropic quisqualate (Qm) receptor sites.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

Signaling Pathways >> Neuronal Signaling >> iGluR

Natural Products >> Acids and Aldehydes

Research Areas >> Neurological Disease

[Target]

NMDA receptor[1]

[In Vitro]

Ibotenic acid (Ibo) is capable of acting at both NMDA and trans-ACPD receptors in the CNS, although only activation of NMDA receptors is involved in Ibo neurotoxicity. Ibotenic acid is toxic to cortical neurons exposes for 5 min with an EC50=77.3±8 μM (n=5) as measured by release of lactate dehydrogenase to the culture media[1].

[References]

[1]. Zinkand WC, et al. Ibotenic acid mediates neurotoxicity and phosphoinositide hydrolysis by independent receptormechanisms. Mol Chem Neuropathol. 1992 Feb-Apr;16(1-2):1-10.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
458.8±45.0 °C at 760 mmHg

[ Melting Point ]:
141-147 °C

[ Molecular Formula ]:
C₅H₆N₂O₄

[ Molecular Weight ]:
158.112

[ Flash Point ]:
231.3±28.7 °C

[ Exact Mass ]:
158.032761

[ PSA ]:
109.58000

[ LogP ]:
-1.07

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.610

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S45-S38-S36/37/39-S28A-S22

[ RIDADR ]:
1544

[ RTECS ]:
NY2100000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Audition-independent vocal crystallization associated with intrinsic developmental gene expression dynamics.

J. Neurosci. 35(3) , 878-89, (2015)

Complex learned behavior is influenced throughout development by both genetic and environmental factors. Birdsong, like human speech, is a complex vocal behavior acquired through sensorimotor learning...

Assessment of sensorimotor gating following selective lesions of cholinergic pedunculopontine neurons.

Eur. J. Neurosci. 40(10) , 3526-37, (2014)

Sensorimotor gating is the state-dependent transfer of sensory information into a motor system. When this occurs at an early stage of the processing stream it enables stimuli to be filtered out or par...

Dopamine D2 Modulation of Sign and Goal Tracking in Rats.

Neuropsychopharmacology 40 , 2096-102, (2015)

In Pavlovian conditioning, sign- and goal-tracking behaviors represent different approaches towards the conditioned stimulus. These behavioral patterns have been associated with predictive or incentiv...