Details
Stereochemistry | RACEMIC |
Molecular Formula | C5H9NO4 |
Molecular Weight | 147.1293 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(CC(O)=O)C(O)=O
InChI
InChIKey=HOKKHZGPKSLGJE-UHFFFAOYSA-N
InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)
N-Methyl-DL-Aspartic Acid (NMDLA) represents a racemic mixture of D and L enantiomers (NMDA; NMLA). Each enantiomer has different biological activities and different natural tissue/species abundances. Therefore, each enantiomer should be considered separately. NMDA is a widely studied neurotoxin which is an agonist of the NMDA receptor and induces brain legions. NMDA is not normally found in tissues, while NMLA can be found naturally in some bivalves.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8561964
Curator's Comment: referenced study was conducted on mice
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1456842 |
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Target ID: CHEMBL2094133 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7871049 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Plasma interleukin-1beta, prolactin, ACTH and corticosterone responses to endotoxin after damage of the anterior hypothalamic area. | 2001 |
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Anticonvulsant activity of aqueous extract of Leonotis leonurus. | 2002 Apr |
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Effects of xenon on in vitro and in vivo models of neuronal injury. | 2002 Jun |
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Variability analyses suggest that supraspino-spinal interactions provide dynamic stability in motor control. | 2002 Mar 15 |
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The respective contribution of lumbar segments to the generation of locomotion in the isolated spinal cord of newborn rat. | 2002 Nov |
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Neuroprotective and neurotoxic properties of the 'inert' gas, xenon. | 2002 Nov |
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Reticulospinal neurons receive direct spinobulbar inputs during locomotor activity in lamprey. | 2004 Sep |
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Seasonal differences in the secretion of luteinising hormone and prolactin in response to N-methyl-DL-aspartate in starlings (Sturnus vulgaris). | 2005 Feb |
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Locomotor-like rhythms in a genetically distinct cluster of interneurons in the mammalian spinal cord. | 2005 Mar |
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Continuous human metastin 45-54 infusion desensitizes G protein-coupled receptor 54-induced gonadotropin-releasing hormone release monitored indirectly in the juvenile male Rhesus monkey (Macaca mulatta): a finding with therapeutic implications. | 2006 May |
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Elevation of intracellular ca(2+) concentration induced by hypoxia in retinal ganglion cells. | 2007 May-Jun |
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Methods for syntheses of N-methyl-DL-aspartic acid derivatives. | 2007 Nov |
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Photopic ERG negative response from amacrine cell signaling in RCS rat retinal degeneration. | 2008 Jan |
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Anticonvulsant activity of Nylandtia spinosa L. Dumont (Polygalaceae) aqueous and methanol leaf extracts in mice. | 2008 Nov |
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Seasonal differences of gene expression profiles in song sparrow (Melospiza melodia) hypothalamus in relation to territorial aggression. | 2009 Dec 4 |
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Rhythmic cFos expression in the ventral subparaventricular zone influences general activity rhythms in the Nile grass rat, Arvicanthis niloticus. | 2009 Oct |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681002
Curator's Comment: referenced study was conducted on mice
Mice were induced to seizures by intravenous injection of NMDLA 150 mg/kg.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11930910
Tissue slices (0.35 mm thick) from the guinea pig cerebral cortex were prepared and incubated for 40 min in control media contained (mM): NaCl, 124 mM; KCl, 5 mM; KH2PO4, 1.2 mM; MgSO4, 1.2 mM; CaCl2, 2.4mM; NaHCO3, 26 mM and glucose, 10 mM; gassed with O2/CO2 (95:5) at 37°C. The slices were then incubated in control medium or in media containing glutamate or stereoisomers of N-methyl-aspartate. Tissues were also incubated in the same media with 5 mM [1-13C] glucose for various time periods. At the end of the incubation periods, the slices were rapidly removed by filtration, washed, homogenized, and centrifuged. Pellets were kept for protein determination. The supernatant was neutralized and dried by rotary-film evaporation. High concentrations of NMDLA (200 micro-M) resulted in decreases in PCr and ATP greater than NMDA (10 - 400 micro-M) alone. This result suggests that NMLA may be contributing more to tissue damage than NMDA, and was confirmed when tissues were exposed to NMLA (400 micro-M) alone. There was a significant increase in lactate and decrease in NAA within 30 min of exposure to 10 micro-M NMDA when Mg+ was absent from solution, but at longer times of exposure ( > 1hr) or higher concentrations of NMDA (400 micro-M these changes were also significant in the presence of Mg. The effects of the stereoisomers (NMDLA and NMLA; 20 - 800 micro-M) on lactate and NAA were essentially similar to those of NMDA itself.
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DSLD |
3436 (Number of products:19)
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4376
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17833-53-3
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EU52DFC4WJ
Created by
admin on Sat Dec 16 11:21:03 GMT 2023 , Edited by admin on Sat Dec 16 11:21:03 GMT 2023
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SUBSTANCE RECORD