5-[amino(2H2)methyl]-1,2-oxazol-3-ol hydrochloride

• ChemBase ID: 174866
• Molecular Formular: C4H7ClN2O2
• Molecular Mass: 151.5569889
• Monoisotopic Mass: 151.01664005
• SMILES: c1c(onc1O)C[15NH2].Cl
• Canonical SMILES: [15NH2]Cc1cc(no1)O.Cl
• InChI: InChI=1S/C4H6N2O2.ClH/c5-2-3-1-4(7)6-8-3;/h1H,2,5H2,(H,6,7);1H/i5+1
• InChIKey: IIDOLBNZAZXSHC-LJJZSEGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[amino(^2H₂)methyl]-1,2-oxazol-3-ol hydrochloride
• IUPAC Traditional name: 5-[amino(^2H₂)methyl]-1,2-oxazol-3-ol hydrochloride
• Synonyms: 5-Aminomethyl-3-hydroxyisoxazole-15N,d2 Hydrochloride; 5-(Aminomethyl)-3(2H)-isoxazolone-15N,d2 Hydrochloride; Muscimol-15N,d2 Hydrochloride

Database IDs

• PubChem SID: 164230776
• PubChem CID: 71750867

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: 10.368288 Å^3
• Polar Surface Area: 72.28 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M815002

Labelled Muscimol (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)