lithium(1+) ion 2-{methyl[(3R)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]amino}acetate

• ChemBase ID: 153947
• Molecular Formular: C19H19F3LiNO3
• Molecular Mass: 373.2952696
• Monoisotopic Mass: 373.14770768
• SMILES: [Li+].CN(CC[C@H](c1ccccc1)Oc1ccc(cc1)C(F)(F)F)CC(=O)[O-]
• Canonical SMILES: [O-]C(=O)CN(CC[C@H](c1ccccc1)Oc1ccc(cc1)C(F)(F)F)C.[Li+]
• InChI: InChI=1S/C19H20F3NO3.Li/c1-23(13-18(24)25)12-11-17(14-5-3-2-4-6-14)26-16-9-7-15(8-10-16)19(20,21)22;/h2-10,17H,11-13H2,1H3,(H,24,25);/q;+1/p-1/t17-;/m1./s1
• InChIKey: VMQXVSNARQMSDL-UNTBIKODSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: lithium(1+) ion 2-{methyl[(3R)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]amino}acetate
• IUPAC Traditional name: lithium(1+) ion 2-{methyl[(3R)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]amino}acetate
• Synonyms: R-(-)-N-Methyl-N-[3-[(4-trifluoromethyl)phenoxy]-3-phenyl-propyl]glycine lithium salt; Org 24598 lithium salt

Database IDs

• CAS Number: 722456-08-8
• MDL Number: MFCD08705419
• PubChem SID: 24898046; 162248086
• PubChem CID: 16219807

CALCULATED PROPERTIES

• Acid pKa: 1.3035002
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.3037857
• LogD (pH = 7.4): 1.3020864
• Log P: 1.3037537
• Molar Refractivity: 102.5839 cm^3
• Polarizability: 34.610764 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: white to off-white solid

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H19F3LiNO3

DETAILS

Sigma Aldrich - O7639

Biochem/physiol Actions
Org 24598 is a selective, potent inhibitor of glial GlyT (GlyT1, glycine transporter type 1). In rats (P12-P16) and in the presence of kynurenic acid, 6-cyano-7-nitroquinoxaline-2,3-dione (CNQX) and bicuculline, ORG 24598 at a concentration of 10 μM induced a mean inward current of -10/-50 pA at -60 mV and increased significantly the decay time constants of miniature (mIPSCs), spontaneous (sIPSCs) and electrically evoked glycinergic (eIPSCs) inhibitory postsynaptic currents. Replacing extracellular sodium with N-methyl-d-glucamine or superfusing the slice with micromolar concentrations of glycine also increased the decay time constant of glycinergic IPSCs. Glycine (1-5 μM and d-serine (10 μM) increased the amplitude of eEPSCs whereas l-serine had no effect. Org 24598 increased significantly the amplitude of NMDA receptor-mediated eEPSCs without affecting the amplitude of non-NMDA receptor-mediated eEPSCs. This brings conclusion that blocking glial glycine transporter by Org 24598 increased the level of glycine in spinal cord slices, which in turn prolonged the duration of glycinergic synaptic current and potentiated the NMDA-mediated synaptic response.