3-methyl-5-[(2S)-1-methylpyrrolidin-2-yl]-1,2-oxazole hydrochloride

• ChemBase ID: 153718
• Molecular Formular: C9H15ClN2O
• Molecular Mass: 202.6812
• Monoisotopic Mass: 202.08729079
• SMILES: Cc1cc(on1)[C@@H]1CCCN1C.Cl
• Canonical SMILES: CN1CCC[C@H]1c1onc(c1)C.Cl
• InChI: InChI=1S/C9H14N2O.ClH/c1-7-6-9(12-10-7)8-4-3-5-11(8)2;/h6,8H,3-5H2,1-2H3;1H/t8-;/m0./s1
• InChIKey: VOXHERKWAIEJQF-QRPNPIFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-5-[(2S)-1-methylpyrrolidin-2-yl]-1,2-oxazole hydrochloride
• IUPAC Traditional name: 3-methyl-5-[(2S)-1-methylpyrrolidin-2-yl]-1,2-oxazole hydrochloride
• Synonyms: 3-Methyl-5-[(2S)-1-methyl-2-pyrrolidinyl]isoxazole hydrochloride; ABT-418 hydrochloride

Database IDs

• CAS Number: 147388-83-8
• MDL Number: MFCD11045960
• PubChem SID: 162247857; 24724395
• PubChem CID: 10375597

CALCULATED PROPERTIES

• LogD (pH = 5.5): -1.9287518
• LogD (pH = 7.4): -0.15744549
• Log P: 0.7961238
• Molar Refractivity: 47.7229 cm^3
• Polarizability: 18.074957 Å^3
• Polar Surface Area: 29.27 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• H Acceptors: 2
• H Donor: 0

PROPERTIES

Physical Property

• Solubility: H2O: soluble15 mg/mL
• Apperance: powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 7/9-22-28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• RID/ADR: UN 2811 6.1/PG 2

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C9H14N2O · HCl

DETAILS

Sigma Aldrich - A6476

Biochem/physiol Actions
Neuronal nicotinic acetylcholine receptor agonist with cognition enhancing and anxiolytic activities.
Legal Information
Subject to U.S. Patent No. 5409946 and sold under license from Abbott Laboratories.
Application
ABT-418 [(S)-3-methyl-5-(1 methyl-2-pyrrolidinyl)isoxazole hydrochloride] is a novel neuronal nicotinic acetylcholine receptor (nAChR) ligand with cognitive enhancing and anxiolytic-like activity 3- to 10-fold more potent than (-)-nicotine in rodents. ABT-418 hydrochloride has been used to study new therapeutic approaches for the treatment of Alzheimer’s disease.