(2R)-2-(methylamino)butanedioic acid

• ChemBase ID: 103948
• Molecular Formular: C5H9NO4
• Molecular Mass: 147.12926
• Monoisotopic Mass: 147.05315777
• SMILES: CN[C@H](CC(=O)O)C(=O)O
• Canonical SMILES: CN[C@@H](C(=O)O)CC(=O)O
• InChI: InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m1/s1
• InChIKey: HOKKHZGPKSLGJE-GSVOUGTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-(methylamino)butanedioic acid
• IUPAC Traditional name: N methyl D aspartate
• Synonyms: (R)-2-(Methylamino)succinic acid; N-Methyl-D-aspartic acid; NMDA (N-Methyl-D-aspartic acid); N-Methylaspartate; N-Methyl-D-aspartate; NMDA; N-Me-D-Asp-OH; N-METHYL-D-ASPARTIC ACID; N-甲基-D-天冬氨酸

Database IDs

• CAS Number: 6384-92-5
• MDL Number: MFCD00004226
• Beilstein Number: 1724431
• PubChem SID: 162090971; 24277987
• PubChem CID: 22880
• CHEBI ID: 31882
• CHEMBL: 291278
• Chemspider ID: 21436
• KEGG ID: C12269
• MeSH Name: N-Methylaspartate
• Wikipedia Title: N-Methyl-D-aspartic_acid

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 1.4571203
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.8783696
• LogD (pH = 7.4): -5.6304536
• Log P: -3.2736425
• Molar Refractivity: 31.3073 cm^3
• Polarizability: 12.69048 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 4

PROPERTIES

Physical Property

• Apperance: white solid; White, opaque crystals
• Melting Point: 189 - 190°C
• Partition Coefficient: 1.39
• Optical Rotation: [α]20/D -15.0±1°, c = 2% in H2O
• pKa: 2.206
• pKb: 11.791
• Odor: Odorless

Safety Information

• RTECS: CI9457000
• German water hazard class: 3
• Safety Statements: S22, S24/25
• LD50: 137 mg kg^-1 (intraperitoneal, mouse)
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: GluR
• Gene Information: human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907)rat ... Gria1(50592), Grik1(29559), Grin2a(24409)

Product Information

• Purity: ≥98% (TLC); ≥98.0% (TLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C5H9NO4

DETAILS

Sigma Aldrich - M3262

Biochem/physiol Actions
Excitotoxic amino acid. Prototypic agonist at the NMDA-type glutamate receptor that regulates ion channels; important in long-term potentiation, ischemia, and epilepsy.

Sigma Aldrich - 65831

Other Notes
Excitatory amino acid, neurotransmitter1; Long term potentiation in the hippocampus - mechanisms of initiation and modulation by neurotransmitters, review2; In vitro modulation of excitatory amino acid responses by serotonin in the cat neocortex3