2-amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid hydrobromide

• ChemBase ID: 75581
• Molecular Formular: C7H11BrN2O4
• Molecular Mass: 267.07724
• Monoisotopic Mass: 265.99021884
• SMILES: n1c(O)c(c(o1)C)CC(C(=O)O)N.Br
• Canonical SMILES: OC(=O)C(Cc1c(C)onc1O)N.Br
• InChI: InChI=1S/C7H10N2O4.BrH/c1-3-4(6(10)9-13-3)2-5(8)7(11)12;/h5H,2,8H2,1H3,(H,9,10)(H,11,12);1H
• InChIKey: KUAHVIUZGLGASU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid hydrobromide
• IUPAC Traditional name: AMeP hydrobromide; AMPA hydrobromide
• Synonyms: D,L-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic Acid Hydrobromide; γ-Amino-3-hydroxy-5-methylisoxazole-4-propionic Αcid Hydrobromide; (R,S)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid Hydrobromide; (+/-)-AMPA hydrobromide; (+/-)-2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoic acid hydrobromide; (±)-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid hydrobromide; (±)-AMPA hydrobromide; AMPA; (±)-α-AMINO-3-HYDROXY-5-METHYL-ISOXAZOLE-4-PROPIONIC ACID

Database IDs

• CAS Number: 171259-81-7; 118896-96-1
• MDL Number: MFCD00055183
• PubChem SID: 162040499; 24277979
• PubChem CID: 11957558

CALCULATED PROPERTIES

• Acid pKa: 1.5563054
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.4256098
• LogD (pH = 7.4): -3.4511206
• Log P: -2.3328915
• Molar Refractivity: 44.0024 cm^3
• Polarizability: 16.434475 Å^3
• Polar Surface Area: 109.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble16 mg/mL; ethanol: soluble1.8 mg/mL; H2O: ≥10 mg/L; H2O: soluble1.2 mg/mL; Methanol; Water
• Apperance: off-white to light tan powder; white; White to Off-White Solid
• Melting Point: 185°C; 205-208°C

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C, Desiccate
• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... GRIA1(2890), GRIA2(2891), GRIA3(2892), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIK5(2901)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C7H10N2O4 · HBr

DETAILS

MP Biomedicals - 02154747

(AMPA) Hydrobromide Potent quisqualate-like agonist

Apollo Scientific Ltd - OR1155T

Racemic mixture

Sigma Aldrich - A9111

Biochem/physiol Actions
(±)-AMPA is a potent excitatory amino acid that interacts selectively with central AMPA/kainate receptors.

Sigma Aldrich - G017

Biochem/physiol Actions
(±)-AMPA is a potent excitatory amino acid that interacts selectively with central AMPA/kainate receptors.

Toronto Research Chemicals - A611550

A potent and selective agonist of the excitatory neurotransmitter L-glutamic Acid. AMPA does not interfere with binding sites for kainic acid in vitro, and AMPA- induced neuronal excitation is not significantly affected by NMDA antagonists.

REFERENCES

• Krogsgaard-Larsen, P., et al., Nature (London), 284: 64, (1980).
• Honore, T., et al., J. Neurochem., 38: 173, (1982).
• MacDonald, J.F., et al.: Science, 253, 1132 (1991)
• Krogsgaard-Larsen, et al.: Nature, 284, 64 (1980)
• Honore, T., et al.: J. Neurochem., 38, 173 (1980)