4-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol hydrochloride

• ChemBase ID: 131493
• Molecular Formular: C17H22ClNO3
• Molecular Mass: 323.81448
• Monoisotopic Mass: 323.12882125
• SMILES: C[C@@H]([C@@H](c1ccc(cc1)O)O)NCCc1ccc(cc1)O.Cl
• Canonical SMILES: Oc1ccc(cc1)CCN[C@H]([C@@H](c1ccc(cc1)O)O)C.Cl
• InChI: InChI=1S/C17H21NO3.ClH/c1-12(17(21)14-4-8-16(20)9-5-14)18-11-10-13-2-6-15(19)7-3-13;/h2-9,12,17-21H,10-11H2,1H3;1H/t12-,17-;/m0./s1
• InChIKey: IDLSITKDRVDKRV-XHXSRVRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol hydrochloride
• IUPAC Traditional name: 4-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol hydrochloride
• Synonyms: N-(p-Hydroxyphenethyl)-4-hydroxynorephedrine hydrochloride; Ritodrine hydrochloride; N-[2-(p-Hydroxyphenyl)ethyl]-N-[2-(p-hydroxyphenyl)-2-hydroxy-1-methylethyl]amine Hydrochloride; N-(p-Hydroxyphenylethyl)-4-hydroxynorephedrine Hydrochloride; Du-21220; Miolene; Prempar; Pre-Par; Ritodrine Hydrochloride

Database IDs

• CAS Number: 23239-51-2
• EC Number: 245-514-8
• MDL Number: MFCD01657514
• PubChem SID: 24278672; 162225771
• PubChem CID: 31728

CALCULATED PROPERTIES

• Acid pKa: 9.154391
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.4678472
• LogD (pH = 7.4): 0.5068871
• Log P: 1.8155849
• Molar Refractivity: 83.0167 cm^3
• Polarizability: 32.40149 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 201-203°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• RTECS: DO6524000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

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

DETAILS

Sigma Aldrich - R0758

Biochem/physiol Actions
β2-adrenoceptor agonist; relaxes uterine muscle contraction.

Toronto Research Chemicals - R533700

A β2-Adrenergic agonist.

REFERENCES

• Coutinho, et al.: Am. J. Obstet. Gynecol., 104, 1053 (1969)
• Wesselius-De Casparis, et al.: Brit. Med. J., 3, 144 (1969)
• Larsen, J.F., et al.: Obstet. Gynecol., 67, 607 (1986)