5-(aminomethyl)-1,2-oxazol-3-ol

• ChemBase ID: 174865
• Molecular Formular: C4H6N2O2
• Molecular Mass: 114.10264
• Monoisotopic Mass: 114.04292744
• SMILES: c1c(onc1O)CN
• Canonical SMILES: NCc1cc(no1)O
• InChI: InChI=1S/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7)
• InChIKey: ZJQHPWUVQPJPQT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(aminomethyl)-1,2-oxazol-3-ol
• IUPAC Traditional name: muscimol
• Synonyms: 5-Aminomethyl-3-hydroxyisoxazole; 5-(Aminomethyl)-3(2H)-isoxazolone; Agarin; Agarine; NSC 333569; Pantherine; Muscimol

Database IDs

• CAS Number: 2763-96-4
• PubChem SID: 164230775
• PubChem CID: 4266

CALCULATED PROPERTIES

• Acid pKa: 5.7831507
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.977992
• LogD (pH = 7.4): -0.77039915
• Log P: -0.65293354
• Molar Refractivity: 28.1453 cm^3
• Polarizability: 10.367029 Å^3
• Polar Surface Area: 72.28 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Beige Solid
• Melting Point: >146°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Hygroscopic, Store in Freezer at -20°C

DETAILS

Toronto Research Chemicals - M815000

A potent but toxic structural analogue of g-aminobutyric acid (GABA), with a zwitterionic structure that can cross the blood-brain barrier.

REFERENCES

• Smart, T., et al.: Br. J. Pharmacol., 103, 1837 (1991)
• Holden, J., et al.: J. Biol. Chem., 277, 18785 (1991)