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

• ChemBase ID: 280
• Molecular Formular: C9H13NO
• Molecular Mass: 151.20562
• Monoisotopic Mass: 151.09971404
• SMILES: O[C@H]([C@H](N)C)c1ccccc1
• 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-/m1/s1
• InChIKey: DLNKOYKMWOXYQA-VXNVDRBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-2-amino-1-phenylpropan-1-ol
• IUPAC Traditional name: phenylpropanolamine
• Brand Name: Acutrim; Ami-Tex; Codimal; Conex; Contuss; Despec; Dexatrim; Dura-Vent; Entex; Gentab; Guaipax; Myminic; Naldecon; Nolex; Partuss; Phenoxine; Phenyldrine; Phenylfenesin; Propagest; Rhindecon; Rhymed; Snaplets; Triaminic; ULR; Vanex
• Synonyms: (1S,2R)-2-Amino-1-phenyl-1-propanol; erythro-α-(1-aminoethyl)benzyl alcohol; D-(+)-Norephedrine; Phenylpropanolamine; (1S,2R)-(+)-Norephedrine; (+-)-Phenylpropanolamine; (+/-)-Norephedrin; PPA; Phenylpropanolamine; D-(+)-Norephedrine; (1S,2R)-2-氨基-1-苯基-1-丙醇; D-(+)-去甲麻黄素; 苯丙醇胺; 赤型-α-(1-氨基乙基)苄醇; (1S,2R)-(+)-去甲麻黄素; D-(+)-去甲麻黄素

Database IDs

• CAS Number: 37577-28-9; 14838-15-4
• MDL Number: MFCD00064411
• Beilstein Number: 2802896
• PubChem SID: 24886491; 160963743; 24859081; 46508087
• PubChem CID: 26934

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 0.57
• LOG S: -0.87
• Solubility (Water): 2.06e+01 g/l

PROPERTIES

Physical Property

• Solubility: Freely soluble
• Melting Point: 51-54 °C(lit.)
• Flash Point: 113 °C; 235.4 °F
• Optical Rotation: [α]20/D +40.0±1°, c = 7% in 1 M HCl; [α]20/D +40°, c = 7 in 1 M HCl
• Hydrophobicity(logP): 1

Safety Information

• 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

Product Information

• Purity: ≥98.0% (NT); 98%
• Grade: purum
• Linear Formula: C6H5CH(OH)CH(CH3)NH2
• Empirical Formula (Hill Notation): C9H13NO

DETAILS

DrugBank - DB00397

• Drug Groups: approved; withdrawn
• Description: Phenylpropanolamine has been withdrawn in Canada. In November 2000, the Food and Drug Administration (FDA) issued a public health advisory against the use of the drug.
• Indication: For the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.
• Pharmacology: Phenylpropanolamine (PPA), a sympathomimetic agent structurally similar to pseudoephedrine, is used to treat nasal congestion. Phenylpropanolamine is found in appetite suppressant formulations and with guaifenesinin in cough-cold formulations. In 2000, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine, due to an increased risk of hemorrhagic stroke in women who used phenylpropanolamine.
• Toxicity: May induce ventricular extrasystoles and short paroxysms of ventricular tachycardia, a sensation of fullness in the head and tingling of the extremities; LD₅₀=1490mg/kg (orally in rat)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Reduced bioavailability (about 38%) from gastrointestinal tract because of first pass metabolism by monoamine oxidase in the stomach and liver.
• Half Life: 2.1 to 3.4 hours.
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - 317500

Packaging
10, 50 g in glass bottle