(2R,3S)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-3-[(propan-2-yl)amino]butan-2-ol hydrochloride

• ChemBase ID: 134044
• Molecular Formular: C17H28ClNO2
• Molecular Mass: 313.86272
• Monoisotopic Mass: 313.18085682
• SMILES: Cc1ccc(c2c1CCC2)OC[C@@H]([C@H](C)NC(C)C)O.Cl
• Canonical SMILES: CC(N[C@H]([C@H](COc1ccc(c2c1CCC2)C)O)C)C.Cl
• InChI: InChI=1S/C17H27NO2.ClH/c1-11(2)18-13(4)16(19)10-20-17-9-8-12(3)14-6-5-7-15(14)17;/h8-9,11,13,16,18-19H,5-7,10H2,1-4H3;1H/t13-,16-;/m0./s1
• InChIKey: KBXMBGWSOLBOQM-LINSIKMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-3-[(propan-2-yl)amino]butan-2-ol hydrochloride
• IUPAC Traditional name: (2R,3S)-3-(isopropylamino)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]butan-2-ol hydrochloride
• Synonyms: (±)-1-[2,3-(Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-2-butanol hydrochloride; ICI 118,551 hydrochloride; (2R,3R)-rel-1-[(2,3-Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-2-butanol Hydrochloride; (R*,R*)-1-[(2,3-Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-2-butanol Hydrochloride; ICI 111581; ICI 118551 Hydrochloride; (2R,3S)-rel-1-[(2,3-Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-2-butanol Hydrochloride; (R*,S*)-()-1-[(2,3-Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-2-butanol Hydrochloride; threo-ICI 118551 Hydrochloride

Database IDs

• CAS Number: 72795-01-8; 72795-04-1; 72795-19-8
• MDL Number: MFCD00153812
• PubChem SID: 162228321; 24277782
• PubChem CID: 25102594

CALCULATED PROPERTIES

• Acid pKa: 13.816111
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.329761
• LogD (pH = 7.4): 1.2247218
• Log P: 3.5319011
• Molar Refractivity: 82.7167 cm^3
• Polarizability: 32.452805 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: white powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADRB2(154)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - I127

Biochem/physiol Actions
ICI 118,551 hydrochloride is a highly selective β2-adrenoceptor antagonist.
Caution
Hygroscopic

Toronto Research Chemicals - I163855

The (S,S)-enantiomer of ICI 118551 as highly selective β2-adrenoceptor antagonist. It is the most potent enantiomer.

Toronto Research Chemicals - I163850

The (R,R)-enantiomer of ICI 118551 as highly selective β2-adrenoceptor antagonist. The S,S-enantiomer is the most potent.

REFERENCES

• Bilski, A., et al.: J. Cardiovasc. Pharmacol., 5, 430 (1983)
• Furse, K., et al.: J. Med. Chem., 46, 4450 (1983)
• Cherezov, V., et al.: Science, 318, 1258 (1983)
• Bilski, A., et al.: J. Cardiovasc. Pharmacol., 5, 430 (1983)
• Furse, K., et al.: J. Med. Chem., 46, 4450 (1983)
• Cherezov, V., et al.: Science, 318, 1258 (1983)