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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
Structure of N-METHYL-DL-ASPARTIC ACID

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)

HIDE SMILES / InChI

Molecular Formula C5H9NO4
Molecular Weight 147.1293
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Curator's Comment: referenced study was conducted on mice

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Plasma interleukin-1beta, prolactin, ACTH and corticosterone responses to endotoxin after damage of the anterior hypothalamic area.
2001
Anticonvulsant activity of aqueous extract of Leonotis leonurus.
2002 Apr
Effects of xenon on in vitro and in vivo models of neuronal injury.
2002 Jun
Variability analyses suggest that supraspino-spinal interactions provide dynamic stability in motor control.
2002 Mar 15
The respective contribution of lumbar segments to the generation of locomotion in the isolated spinal cord of newborn rat.
2002 Nov
Neuroprotective and neurotoxic properties of the 'inert' gas, xenon.
2002 Nov
Effect of glutamate on basal steroidogenesis by ovarian follicles of rainbow trout (Oncorhynchus mykiss).
2004 May
Altered sensorimotor development in a transgenic mouse model of amyotrophic lateral sclerosis.
2004 Nov
Reticulospinal neurons receive direct spinobulbar inputs during locomotor activity in lamprey.
2004 Sep
Seasonal differences in the secretion of luteinising hormone and prolactin in response to N-methyl-DL-aspartate in starlings (Sturnus vulgaris).
2005 Feb
Locomotor-like rhythms in a genetically distinct cluster of interneurons in the mammalian spinal cord.
2005 Mar
Morphological evidence that xenon neuroprotects against N-methyl-DL-aspartic acid-induced damage in the rat arcuate nucleus: a time-dependent study.
2006 Aug
Anticonvulsant activity of Cotyledon orbiculata L. (Crassulaceae) leaf extract in mice.
2007 May 30
Anticonvulsant activity of Nylandtia spinosa L. Dumont (Polygalaceae) aqueous and methanol leaf extracts in mice.
2008 Nov
Seasonal differences of gene expression profiles in song sparrow (Melospiza melodia) hypothalamus in relation to territorial aggression.
2009 Dec 4
Rhythmic cFos expression in the ventral subparaventricular zone influences general activity rhythms in the Nile grass rat, Arvicanthis niloticus.
2009 Oct
Patents

Sample Use Guides

In Vivo Use Guide
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:21:03 GMT 2023
Edited
by admin
on Sat Dec 16 11:21:03 GMT 2023
Record UNII
EU52DFC4WJ
Record Status Validated (UNII)
Record Version
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Name Type Language
N-METHYL-DL-ASPARTIC ACID
Systematic Name English
ASPARTIC ACID, N-METHYL-
Systematic Name English
METHYL ASPARTIC ACID, DL-
Systematic Name English
N-METHYL-DL-ASPARTATE
Systematic Name English
DL-N-METHYLASPARTIC ACID
Common Name English
Classification Tree Code System Code
DSLD 3436 (Number of products:19)
Created by admin on Sat Dec 16 11:21:03 GMT 2023 , Edited by admin on Sat Dec 16 11:21:03 GMT 2023
Code System Code Type Description
PUBCHEM
4376
Created by admin on Sat Dec 16 11:21:03 GMT 2023 , Edited by admin on Sat Dec 16 11:21:03 GMT 2023
PRIMARY
CAS
17833-53-3
Created by admin on Sat Dec 16 11:21:03 GMT 2023 , Edited by admin on Sat Dec 16 11:21:03 GMT 2023
PRIMARY
FDA UNII
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
PRIMARY