2-(2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole hydrochloride

• ChemBase ID: 132689
• Molecular Formular: C11H13ClN2O2
• Molecular Mass: 240.68612
• Monoisotopic Mass: 240.06655535
• SMILES: c1ccc2c(c1)OCC(O2)C1=NCCN1.Cl
• Canonical SMILES: C1CN=C(N1)C1COc2c(O1)cccc2.Cl
• InChI: InChI=1S/C11H12N2O2.ClH/c1-2-4-9-8(3-1)14-7-10(15-9)11-12-5-6-13-11;/h1-4,10H,5-7H2,(H,12,13);1H
• InChIKey: MYUBYOVCLMEAOH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole hydrochloride
• IUPAC Traditional name: idazoxan hydrochloride
• Synonyms: (±)-2-[1,4-Benzodioxan-2-yl]-2-imidazoline hydrochloride; RX 781094; Idazoxan hydrochloride; 2-(2,3-Dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole Hydrochloride; (+/-)-Idazoxan Monohydrochloride; RX 781094A; Idazoxan Hydrochloride

Database IDs

• CAS Number: 79944-56-2
• MDL Number: MFCD00069293
• PubChem SID: 24278493; 162226966
• PubChem CID: 154494

CALCULATED PROPERTIES

• Acid pKa: 17.071854
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.71076983
• LogD (pH = 7.4): 0.61873114
• Log P: 0.76896405
• Molar Refractivity: 54.549 cm^3
• Polarizability: 21.304382 Å^3
• Polar Surface Area: 42.85 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• Safety Statements: 7
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... ADRA2A(150), ADRA2B(151), ADRA2C(152)

DETAILS

Sigma Aldrich - I6138

Biochem/physiol Actions
α2-adrenoceptor antagonist; I2 imidazoline receptor agonist; I1 imidazoline receptor antagonist

Toronto Research Chemicals - I506800

An α-adrenoceptor antagonist; in rat brain Idazoxan is a pure antagonist and it has a selectivity for α2- over α1-receptors markedly superior to Piperoxane, Yohimbine, or Rauwolscine. Antiparkinsonian.

REFERENCES

• Fliri, A., et al.: Med. Chem., 48, 6918 (2005)
• Yildirim, M., et al.: Nat. Biotechnol., 25, 1119 (2005)