2-[(1S)-1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole

• ChemBase ID: 172360
• Molecular Formular: C11H12Cl2N2O
• Molecular Mass: 259.13178
• Monoisotopic Mass: 258.03266837
• SMILES: c1(c(c(ccc1)Cl)O[C@H](C1=NCCN1)C)Cl
• Canonical SMILES: C[C@@H](C1=NCCN1)Oc1c(Cl)cccc1Cl
• InChI: InChI=1S/C11H12Cl2N2O/c1-7(11-14-5-6-15-11)16-10-8(12)3-2-4-9(10)13/h2-4,7H,5-6H2,1H3,(H,14,15)/t7-/m0/s1
• InChIKey: KSMAGQUYOIHWFS-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S)-1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole
• IUPAC Traditional name: lofexidine hydrochloride
• Synonyms: 2-[(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenylethanoneHydrochloride; Lobeline Hydrochloride; (-)-Lobeline Hydrochloride; (-)-α-Lobeline Hydrochloride; Lobelin Hydrochloride; Lobron; Zoolobelin; α-Lobeline Hydrochcloride; 2-[(1R)-1-(2,6-Dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole; (-)-Lofexidine; Levlofexidine; (R)-Lofexidine

Database IDs

• CAS Number: 81447-78-1; 134-63-4
• PubChem SID: 164228270
• PubChem CID: 208822

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.6871826
• LogD (pH = 7.4): 2.2111351
• Log P: 2.6630576
• Molar Refractivity: 64.413 cm^3
• Polarizability: 25.174986 Å^3
• Polar Surface Area: 33.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 184-186°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L469395

The R-enantiomer of Lofexidine. α2-Adrenoceptor agonist related structurally to Clonidine. Used in treatment of opioid withdrawal symptoms; antihypertensive.

Toronto Research Chemicals - L469350

A neuronal nicotinic acetylcholine receptor agonist. A CNS stimulant.

REFERENCES

• Velly, J., et al.: J. Pharmacol., 8, 351 (1977)
• Jarrot, B., et al.: Biochem. Pharmacol., 28, 141 (1977)
• Birch, P., at al.: Brit. J. Pharmacol., 68, 107 (1977)
• Damaj, M.I., et al.: J. Pharmacol. Exp. Ther., 282, 410 (1997)
• Toth, P.T., et al.: Eur. J. Pharmacol., 363, 75 (1997)
• Flammia, D., et al.: J. Med. Chem., 42, 3726 (1997)
• Dwoskin, P.A., et al.: Biochem. Pharmacol., 63, 89 (1997)