[(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine hydrochloride

• ChemBase ID: 133757
• Molecular Formular: C16H22ClNO2
• Molecular Mass: 295.80438
• Monoisotopic Mass: 295.13390663
• SMILES: CC(C)NC[C@@H](COc1cccc2c1cccc2)O.Cl
• Canonical SMILES: O[C@H](COc1cccc2c1cccc2)CNC(C)C.Cl
• InChI: InChI=1S/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H/t14-;/m0./s1
• InChIKey: ZMRUPTIKESYGQW-UQKRIMTDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine hydrochloride
• IUPAC Traditional name: [(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](isopropyl)amine hydrochloride
• Synonyms: (S)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride; (S)-(-)-Propranolol hydrochloride; (2S)-1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol Hydrochloride; S-(-)-1-Isopropylamino-3-(1-naphthoxy)-2-propanol Hydrochloride; (-)-Propranolol Hydrochloride; (S)-(-)-Propranolol Hydrochloride; L-(-)-Propranolol Hydrochloride; l-Propranolol Chlorhydrate; l-Propranolol Hydrochloride; (S)-Propranolol Hydrochloride; (S)-1-异丙基氨基-3-(1-萘氧基)-2-丙醇 盐酸盐; (S)-(-)-普奈洛尔 盐酸盐

Database IDs

• CAS Number: 4199-10-4
• EC Number: 224-096-0
• MDL Number: MFCD00064547
• Beilstein Number: 3574966
• PubChem SID: 162228034; 24278657; 24887925
• PubChem CID: 165193

CALCULATED PROPERTIES

• Acid pKa: 14.08793
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.6095358
• LogD (pH = 7.4): 0.3584574
• Log P: 2.583696
• Molar Refractivity: 76.8257 cm^3
• Polarizability: 31.766071 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble8.0 mg/mL; DMSO: <14.5 mg/mL; ethanol: soluble10 mg/mL; H2O: soluble50 mg/mL (With heat. Aqueous solutions are most stable at pH 3.0 and decompose rapidly at basic pH. Decomposition is accompanied by discoloration of the solution.)
• Apperance: powder
• Melting Point: 193-195 °C(lit.); 193-197 °C
• Optical Rotation: [α]20/D -25±2°, c = 1% in ethanol; [α]20/D -26°, c = 1 in ethanol; [α]25/D -25.5°, c = 1.0 in ethanol(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADRB1(153), ADRB2(154), ADRB3(155), HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355)

Product Information

• Purity: ≥98% (TLC); ≥99.0% (AT); 98%
• Grade: puriss.
• Optical Purity: enantiomeric ratio: ≥99:1 (HPLC)
• Linear Formula: C10H7OCH2CH(OH)CH2NHCH(CH3)2·HCl

DETAILS

Sigma Aldrich - P8688

包装
100, 500 mg in glass bottle
Biochem/physiol Actions
Active β-adrenoceptor blocking enantiomer, as measured by inhibition of isoprenaline-induced tachycardia; Propranolol is also non-specific 5-HT1A, 5-HT1B and 5-HT1C serotonin receptor antagonist. The stereoselective association of mianserin and propranolol with the 5HT1A, 5HT1B and 5HT1C sites may prove useful in the characterization of these sites

Sigma Aldrich - 82066

Other Notes
β-adrenergic blocker1

Toronto Research Chemicals - P831795

The S-enantiomer of Propranolol (P831800). β-Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

REFERENCES

• Bond, et al.: Nature, 213, 721 (1967)
• Hansteen, V., et al.: Br. Med. J., 284, 155 (1967)
• Diamond, S., et al.: J. Clin. Pharmacol., 28, 193 (1967)