(1R,2S)-2-amino-1-phenylpropan-1-ol

• ChemBase ID: 130289
• Molecular Formular: C9H13NO
• Molecular Mass: 151.20562
• Monoisotopic Mass: 151.09971404
• SMILES: O[C@H](c1ccccc1)[C@@H](N)C
• Canonical SMILES: O[C@H](c1ccccc1)[C@@H](N)C
• InChI: InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
• InChIKey: DLNKOYKMWOXYQA-CBAPKCEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-2-amino-1-phenylpropan-1-ol
• IUPAC Traditional name: fenilpropanolamina
• Synonyms: (αS)-rel-α-[(1R)-1-Aminoethyl]-benzenemethanol; erythro-2-Amino-1-phenyl-1-propanol; (+/-)-Norephedrine; (+/-)-Phenylpropanolamine; Propadrine; dl-Phenylpropanolamine; PPA; (αR)-α-[(1S)-1-Aminoethyl]benzenemethanol; (-)-Norephedrin; (-)-Norephedrine; (-)-Phenylpropanolamine; (R,S)-(-)-Norephedrine; D-Norephedrine; erythro-(1R,2S)-Norephedrine; (1R,2S)-Norephedrine; Phenylpropanolamine; L-(-)-Norephedrine; (1R,2S)-2-Amino-1-phenyl-1-propanol; L-(-)-Norephedrine; (1R,2S)-(-)-Norephedrine; L-(-)-去甲麻黄素; (1R,2S)-2-氨基-1-苯基-1-丙醇; L-(-)-去甲麻黄素; (1R,2S)-(-)-去甲麻黄素

Database IDs

• CAS Number: 14838-15-4; 492-41-1
• EC Number: 207-755-7
• MDL Number: MFCD00008079
• Beilstein Number: 2207678
• PubChem SID: 24857054; 24886492; 162224568
• PubChem CID: 10297
• ATC CODE: R01BA01; QG04BX91
• CHEMBL: 136560
• Chemspider ID: 9875
• DrugBank ID: DB00397
• KEGG ID: D08368
• Unique Ingredient Identifier: 33RU150WUN
• Wikipedia Title: Phenylpropanolamine

CALCULATED PROPERTIES

• Acid pKa: 13.896164
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.0889428
• LogD (pH = 7.4): -1.0537072
• Log P: 0.8852543
• Molar Refractivity: 44.9127 cm^3
• Polarizability: 18.00672 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 41-44°C; 51-53 °C(lit.)
• Flash Point: 113 °C; 235.4 °F
• Optical Rotation: [α]20/D -41.0±1°, c = 7% in 1 M HCl; [α]20/D -41°, c = 7 in 1 M HCl

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• RTECS: RC2275000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 2.1 to 3.4 hours.
• Legal Status: ?-only; Unknown (UK)
• Gene Information: rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413)

Product Information

• Purity: ≥98.0% (NT); 99%
• Grade: purum
• Linear Formula: C6H5CH(OH)CH(CH3)NH2
• Empirical Formula (Hill Notation): C9H13NO

DETAILS

Sigma Aldrich - 282553

Packaging
10, 50 g in glass bottle

Toronto Research Chemicals - N674400

A metabolite of Phenmetrazine. An ephedrine alkaloid, a nervous system stimulant.

Toronto Research Chemicals - P336100

Norephedrine, also called Phenylpropanolamine (PPA), is a synthetic form of the ephedrine alkaloid. Used in treatment of urinary incontinence in dogs and cats; decongestant nasal. After reports of the occurrence of intracranial hemorrhage and other advers

REFERENCES

• Jian, Z., et al.: Planta Med., 54, 69 (1988)
• Tanaka, T., et al.: Nat. Med., 49, 418 (1988)
• Marchei, E., et al.: J. Pharm. Biomed. Anal., 41, 1633 (1988)
• Bowyer, J., et al.: Toxicol. Sci., 2000, 55, 133 (2000)
• Baker, S., et al.: Can. J. Neurol. Sci., 32, 248 (2000)
• Suwalsky, M., et al.: Biophys. Chem., 141, 34 (2000)